My Neighbor's Daughter Ch. 01

My name is Ray, and I've lived alone in a 2300 sq. ft. ranch-style house since my wife Ann passed away in a tragic accident. While a hefty lawsuit settlement has left me financially secure for the rest of my life, all the money in the world couldn't help my loneliness. I still maintain some income from being a freelance writer, but I treat it more as a hobby and something to keep myself busy. I like to play golf and have some beers with my friends, and I attend various sporting events and concerts to pass the time.

I work out every day at the gym to stay in decent shape. I'm nowhere near being a bodybuilder, but I'm toned and in good shape for my age. I have a little bit of a beer belly, but not as bad as most guys my age. It took me a few years to start thinking about dating again, but I'm in my early fifties, and the pickings are slim.

Friends have tried setting me up with women they know, but that hasn't worked out well at all. I wish they would stop trying so hard to play matchmaker and let nature take its course. I've tried online dating, and that hasn't been any better than matchmaking friends. Part of the problem is that I'm not looking for a serious relationship right now or maybe ever. Most of the women my age are looking for a husband, and that's when I run for the hills. I've had a few friends with benefits relationships, but when they started to get serious, I broke it off with them.

More often than I want to admit, I'm left to jerk off to my fantasies while watching Internet porn. It's less complicated than trying to date while I'm in my fifties. Don't get me wrong, I'm not jerking off every night, but sometimes, a guy needs to release the pressure in his balls. I like to have a beer and watch sports on TV out on my back patio. I have a nice inground pool with a diving board and hot tub that I enjoy regularly.

There is a young couple with an infant child on one side of me and a couple around my age on the other. I don't have much of a relationship with either neighbor, but I know the older couple better since they've been there longer.

Felix and Helen have three grown children. Gretchen is the youngest and is finishing up college. I've talked to them over the years, but we don't share many interests. Felix is a computer software engineer, and Helen is a Math professor at a local university. I don't want to call them nerdy, so I'll say they are scholarly. I've had friendly conversations with both of them, but it's not like I can talk sports or play a round of golf with Felix. They don't drink much, so we've never hung out and had a few beers either.

It has been said, "The apple doesn't fall far from the tree," so it isn't surprising that their children are a bit nerdy, er, scholarly, too.

While most kids were going to summer camp to fish, swim, play sports, and tell stories around the campfire, their kids were off to physics or astronomy camps. Hey, to each their own. I'm not going to judge anyone, I'm only trying to give the readers some perspective.

One early summer day, Felix stopped to talk to me while I was out cutting the grass.

"Hi, Ray."

"How's it going, Felix? What's up?"

"I just wanted to let you know that Helen and I are going to be taking a six-week trip through Europe starting next week."

"That's great, Felix. I hope you two have a great time."

"Gretchen is going to stay at the house while we're away. Even though she's twenty-one, I was hoping you'd keep an eye on her and help her out if needed."

"No problem. I'd be happy to help out in any way I can."

"Thanks, Ray. Even though she's an adult, we still worry about our kids. It's nice to know she can go to you if she has to."

"You're welcome. Tell her she can call me any time."

I'd see Gretchen coming and going from her parents' house during her school breaks, but I hadn't talked to her in years. It's not like we communicated a lot anyway. From what I could remember, she was average in height, maybe carrying a few extra pounds, but it was hard to tell because of the way she dressed. The best way to describe her attire is frumpy. She wore long skirts or dresses, or baggy clothes. She wore glasses and kept her hair in a bun most of the time. She resembled the stereotypical librarian.

I almost forgot about my neighbors going out of town until I saw Gretchen coming and going from the house. She hadn't changed much since the last time I saw her. She was dressed in the same frumpy manner. Her dark brown hair was in a bun as usual, and she was wearing a sweatshirt and sweatpants.

Things were pretty quiet around the house for the first few days, but then I saw Gretchen having a hard time starting the lawnmower, so I went over and gave her a hand. It wasn't a big deal, anyone would have given her a hand. Later that same day, her car wouldn't start, so I tried to give it a jump start, but that didn't work. I drove her to the auto parts store to get a new battery and installed it for her.

Gretchen was so appreciative, she told me, "I don't know what I would have done without you today, Ray. Thank you so much."

"You're welcome. I'm glad I could help out. I promised your parents I'd look out for you while they were gone."

"Normally, I don't like them treating me like I'm still a kid, but it worked out for me this time."

"If you ever need anything, don't hesitate to ask me for help."

"Thanks, Ray, I feel like I owe you something for helping me today."

"Ah, you don't owe me anything. It was my pleasure."

"How about if I cook you dinner? I don't have any plans."

I thought about her offer and replied, "How about if we have dinner at my house. I have a pool and a hot tub. We can throw something on the grill and enjoy the nice weather."

"Yeah, that sounds like fun. I'll bring over a couple of strip steaks, and I'll make pasta salad."

"Sounds good. I have plenty to drink too. Soft drinks, beer, or wine."

We had our plans set. Gretchen was going grocery shopping, and when she got back, she would come over. I was happy to have some company to break up the monotony that my life had become.

After spending a good portion of the afternoon with Gretchen, I noticed that behind the glasses, hair in a bun, and frumpy clothes, she was kind of pretty. She was shy in a cute way, with a genuine way about her. There was nothing phony about her. I was looking forward to spending the evening with her.

I straightened up the house and anxiously awaited Gretchen's arrival. I knew it was silly, but I couldn't help myself. I smiled when I heard the doorbell ring. She was wearing an oversized long-sleeved t-shirt and loose shorts.

After I welcomed her inside, I asked, "Did you bring a swimsuit?"

"Yeah, I have it on underneath."

"Good, because that's the first thing I wanted to do. It's hot out there."

"Yeah, I was looking forward to cooling down, too."

After we put the food in the fridge, Gretchen told me she'd like some red wine, so I grabbed a bottle and headed out to the pool. When we got outside, I took off my shirt and waited for my guest to get ready. She seemed a bit shy about taking her outer clothing off, so I jumped into the pool so she wouldn't feel too uncomfortable. I'm a normal guy and was curious to see what she looked like in a bathing suit.

Gretchen was wearing a very modest one-piece swimsuit. It was more fitting of a woman much older than a woman her age. Her swimwear showed no cleavage at all and fully covered her ass. She had pale white skin, and I could tell she wasn't confident in revealing even a small portion of her body.

However, it appeared that Gretchen might be hiding a decent-sized pair of breasts and a well rounded ass that led to some thicker thighs.

I remember thinking to myself, "Uh, she's got a decent body. Too bad she's been hiding it all these years."

She took off her glasses and let down her hair. I don't recall ever seeing her with her hair down before. Gretchen walked slowly down the stairs and waded into the pool before fully submerging herself in the crystal clear water.

"Oh, it feels good to cool off in your pool, Ray. Thanks for inviting me."

We'd swim around and then go to the side of the pool to sip our wine before swimming around again. We were also chatting about her studies and how she also wanted to be a college professor as her long-term goal. She asked me about my writing and some of my hobbies. It was nice to have a conversation with a young lady. It made me wish I had gotten to know her better before that night.

When we got hungry, I fired up the grill and put the steaks on. Gretchen covered herself with a towel as I was grilling the steaks. We had another glass of wine over dinner. She told me she wasn't much of a drinker; she normally stopped after two, but felt pretty good that night.

Gretchen seemed to be relaxing and enjoying herself, and decided to have a third drink while we soaked in the hot tub after dinner. At times, she would get warm and sit on the edge of the hot tub to cool off.

I don't know if it was the alcohol or the fact that I hadn't gotten laid in a while, but I started looking at Gretchen in a more sexual manner. Even though her swimsuit was anything but sexy, I was still checking out her bare legs covered in droplets of water. I was trying to imagine what her breasts and ass looked like. I would sometimes feel guilty for looking at her like that, but the guilt didn't last too long.

At one point, Gretchen asked me, "Is everything okay?"

"Yeah, why do you ask?"

"You keep looking at me."

"For one, you're the only other person here," I said with a chuckle, "and two, I've never seen you with your hair down before. You should do that more often. You look nice with your hair down."

Gretchen blushed a little and replied, "Really, no one has ever said that to me before."

"You have really pretty blue eyes, too."

She gave me a forced smile in response, and I could tell she was uncomfortable with my compliments, but I was sincere in my comments. Gretchen changed the subject as we relaxed. It was nice to have someone to talk to. I had spent many lonely nights in the pool and hot tub. When Gretchen told me she had to leave, I was disappointed and figured she didn't want to hang out with an older guy.

Before she left, I told her, "You know, you can come over anytime you want and use the pool or hot tub. Even if I'm not home, you're always welcome."

"Thanks, Ray. I'll remember that. I had a nice time tonight. Thanks for inviting me."

"I had a great time, too. It was nice talking with you."

I watched as she dried herself off while further admiring her youthful body.

From that day forward, Gretchen and I would talk often, either in person or by text messaging each other. We'd get together to swim or to have meals together. Sometimes it was a morning, coffee, lunch, or dinner. We were becoming quite close. I especially liked the time we spent in the pool.

As we got closer, we felt more comfortable with each other. I told her about how devastated I was to lose my wife at a relatively young age, and she shared that she wasn't that experienced with men and dating.

One evening while we were sitting around the pool having some wine, I told Gretchen, "I hope you don't mind me saying this, but you're a naturally beautiful woman."

She scoffed at my comment and replied, "Alright, if you say so."

"No, you really are. I don't like it when women pile on the makeup. They seem so phony. You're pretty without all the fake stuff. You should have more confidence in yourself."

"I don't feel pretty, and I'm fat."

That's when I scoffed at her comment, "Why do women think they're fat? You look great."

"I've got a fat ass and my boobs are small, not a great combination for attracting guys."

"You've got a nice ass and your breasts are lovely," I replied but realized afterward that I just admitted to checking her out.

"You're just saying that to make me feel better."

"No, I'm not. If you don't mind me saying it, you should consider dressing a little more fashionable."

"No one wants to see my body."

"Oh, I for one, ah, never mind," I started to say before I caught myself. I didn't want Gretchen to think I was looking at her in a sexual manner, even though I was.

We quickly changed the subject, but I could tell she was flattered by my comments. She stayed for another half an hour before saying goodnight.

I went inside to change, have another glass of wine, and catch the end of a ball game on TV. As I was walking by the spare room that I used as an office for writing, I noticed a light come on in one of the bedrooms next door. The shade was up, so I could see into the house. Holy shit, it was Gretchen's room.

I told myself, "Don't look, just go get dressed."

That thought lasted for a split second until I saw Gretchen start to take off her swimsuit. I was frozen in place, hypnotized as I watched her peel down the top of her swimsuit. Oh my goodness, her breasts were even better than I imagined. I moved to a dark corner of the room so she wouldn't see me watching her.

Her breasts were beautifully formed, round, firm, and full. Her nipples were very dark and hard. She pinched them a couple of times and brushed her hands across them while looking at herself in the mirror attached to her dresser. Gretchen then continued to strip off her swimsuit.

The first thing that caught my eye was a full, dark bush of pubic hair, and then her well-cushioned curvy ass. Holy fuck, I wanted to sink my hands into those luscious cheeks. Gretchen twisted and turned in the mirror, checking herself out while I watched while hidden in the corner of my office. My hand found its way to my hardening cock and I unconsciously began stroking it ever so slowly.

I told myself it was wrong to be spying on my youthful neighbor, but that didn't stop me from watching her. Gretchen ran her hands over her body and inserted a finger into her pussy and began to move it around. She then bent over in front of the mirror. I saw her full ass and got an obstructed view of her pussy lips in the reflection.

Gretchen turned around and pulled out a vibrator from her dresser drawer. There was no way I was going to stop watching her now. I stared out the window as she laid down on the bed and spread her legs wide. I thought I could see her pussy glistening from the light in her room as she slowly inserted the vibrator.

As Gretchen fucked herself with the vibrator, she rubbed her nipples with her free hand. I began to stroke myself faster, in time with the insertion of her vibrator. I couldn't help but wish it was my dick inside of her instead of the plastic sex toy. I wanted to kiss her, suck on her nipples, lick her pussy, and fuck her. I fantasized about how tight her inexperienced pussy would feel as I plunged myself into her. In my masturbatory fantasy, she was also thinking about how I would ravage her young body.

When her hips began to wiggle and her free hand drifted down to massage her clit, I knew she was close to orgasm. I was stroking myself faster now, on the verge of cumming too. I saw her body stiffen and her face grimace in pleasure. Her orgasm rippled through her body as I began to cum along with her.

My cum filled the inside of my damp swim trunks as I watched Gretchen bring herself to another quick orgasm before she laid still with the vibrator still inserted inside of her. She rested for a few moments and then left the room. I assumed she went to take a shower, so I did the same.

When I was done showering, I returned to my office to see Gretchen dressed in a long-sleeved T-shirt and no bra. She wore loose sleep shorts and turned out the lights. I fell asleep that night to the nasty thoughts of what I'd like to do with my young neighbor.

Whenever I was in my office or even walking by, I would glance out the window, hoping to catch another glimpse of Gretchen in various states of undress or masturbation. Much to my disappointment, all I saw was a drawn shade.

That made me wonder, "Did she see me watching her?" The hopeful side of me wondered, "Did she leave her shade raised on purpose in the hope that I would see her naked?"

I hadn't seen Gretchen for a couple of days because we were both busy, but on the third day, I sent her a text that read, "Hey, I'm going to get the grill started. I've got some burgers ready to throw on the grill. Let me know if you're interested."

A few minutes later, she responded by saying, "Sounds good. I'll bring a salad."

"Great. Wear your swimsuit, too. I'll be in the pool."

"I was planning on it."

Several minutes later, I heard Gretchen opening the gate to the yard. She was wearing a T-shirt and shorts and carrying a bowl of salad. She took the liberty of putting the salad in an outdoor fridge I had on the patio and then proceeded to take off her outer clothing. I was pleasantly surprised to see her wearing a modest bikini. It showed just a hint of cleavage and a bit of her meaty ass cheeks. The top was a strapless bandeau type.

"Is that a new bikini?" I inquired.

"Yes. I decided to take your advice and try to wear something more fashionable. Do you like it?"

"Yeah, you look great."

I watched as she applied suntan lotion onto her nubile body. Her skin glistened in the sunlight from the lotion. I marvelled at how good she looked and wondered why she kept herself covered up all these years. I guess it's normal for young women to have body image issues, which is a shame.

Gretchen then said, "I got a little sunburn the other day, so I have to be careful. Would you put some lotion on my back, please?"

"Of course I will."

I was hoping she would ask. I squirted some lotion onto Gretchen's back and slowly rubbed it into her soft skin in a circular motion. I accidentally put too much on her, so it took longer to rub it in, but she didn't seem to mind.

"Um, that feels good."

"I've been told I give great back massages," I said as I pressed my fingers deeper into her neck and shoulders.

"Oh god, you sure do. Don't stop."

After the lotion was sufficiently rubbed in, I stopped massaging Gretchen's back, mostly because I was afraid I wouldn't be able to control my urges. My dick was beginning to grow and I didn't want to embarrass myself or her.

When I was done, Gretchen turned around, gave me a sheepish look, and said, "Thank you."

I stupidly replied, "It was my pleasure," then I quickly corrected myself, "I meant, I didn't want you to get sunburned. I'm happy to help out."

Gretchen snickered and replied, "I understand."

In all reality, it was my pleasure. It felt good to touch her young body and to hear her soft sighs of pleasure. I wanted to go further, but knew I couldn't and shouldn't.

I poured us both a glass of wine, and we enjoyed the warm water of the pool for almost an hour. We were in the deep end when we got out of the pool, and I followed Gretchen up the ladder. Her pillowy butt was practically in my face, tiny beads of water were cascading over her cheeks and down her legs. Her bikini bottoms were pulled into the crack of her ass. I was tempted to nibble on her cheeks. I walked behind her until we got to the table where the towels were. Her ass twitched and jiggled with each step. She did not attempt to pull her bikini bottoms out of her ass crack until after she dried herself. Gretchen must have known I was checking her out.

Gretchen didn't cover herself with a towel while I was grilling the burgers or during dinner. I told her I like a beer with my burgers and I stared at her curvaceous ass while bent over getting a couple of cans out of the fridge. I wanted so desperately to walk up behind her, pull her bikini bottoms down, and fuck her right there on the patio but we all know a guy can't act on all of his sexual desires.

Besides, what would she want with an old guy like me anyway? I'm old enough to be her father. That didn't keep me from looking and hoping, though. Maybe she thought it was safe to experiment with her more revealing bikini around me. A guy can always dream about being with a younger woman.

After dinner, we ended up in the pool again with a glass of wine.

As we were chatting, Gretchen said, "It's nice to be able to relax like this. I normally don't have more than two drinks, but it feels good to let loose a little."

"You're too young not to enjoy life to its fullest. Before you know it, you'll be my age and wishing you were young again."

"You're right, Ray. I need to loosen up a little, but it's not easy for me."

"I understand, but I'll try and be a bad influence while you're around," I replied half-jokingly.

"Promise?"

"I promise, but be careful what you ask for," I said with a mischievous grin and wink.

We spent some time swimming in the pool and jumping off the diving board. It was a beautiful summer night with an almost full moon. I kept a watchful eye on Gretchen every time she climbed the ladder to go over to the diving board. Her bikini bottoms crept into the crack of her ass again and I made sure to get nice long looks at her round cheeks and half-naked body.

Gretchen dove into the pool headfirst one time, and before her head broke the surface, her bikini top floated my way. I picked it up and held it in my hand waiting for her to surface. She immediately realized her predicament.

"Throw me my top, please."

My first instinct was to be a gentleman and toss it back to her, but the man inside me thought differently. I decided to tease her a bit instead of throwing it to her.

"Come and get it," I responded as I held it out in my hand.

"Come on, you know I can't."

"Sure, you can. There's nothing stopping you," I said with a smirk.

We went back and forth a couple of times. I don't know if Gretchen was feeling the effects of the alcohol, decided to loosen up somewhat, or a combination of both, but she swam to where her feet touched the bottom of the pool and walked over to me. Her firm, young breasts were totally exposed. My eyes were immediately drawn to the beads of water dripping from her tender nipples, which had hardened either from being wet in the night air, from excitement, or both.

"Can I please have my top now?" Gretchen asked while looking into my eyes.

She called my bluff, and she had to have noticed my eyes being drawn to her breasts. I must have stared too long because she had to ask me a second time to give it back to her.

"Uh, yeah, here it is."

"What do you think?" Gretchen asked.

"About what?"

"My breasts."

"They're magnificent."

Gretchen blushed a bit as she put her top back on. I was concerned that I may have angered her, which is the last thing I wanted. However, she didn't seem phased by it and continued to swim for another hour before we decided to call it a night.

The first thing that came to my mind after Gretchen left was to go into my office and see if her shade was up or down. When I got inside, I was disappointed to see the shade drawn. My disappointment quickly turned to excitement when I saw Gretchen raise the shade in the darkness of her room and then turn the light on.

My first thought was, "Holy shit, she wants me to watch," and I was more than happy to oblige.

I hid in the dark corner of the room again and watched attentively as Gretchen walked around her room before she pulled a nightie out of her drawer. She stood before her dresser mirror and removed her bikini top, exposing those marvelous tits once again. My goodness, I desperately wanted to get my hands and lips on those beauties. She played with her breasts and nipples and then pulled off her bottoms.

Gretchen kept peeking over at the window, which made me wonder if she was looking to see if I was watching. Part of me wanted to let her know I was indeed a voyeur to her naked performance, but I also didn't want to risk being wrong in my assumption. My dick was rock hard by then as I waited to see if she was going to masturbate again.

She left to take a quick shower, and I didn't move from my spot out of fear I'd miss something. I tried not to touch myself too much because I wanted to wait to see what Gretchen would do next. I let out a sigh of joy when I saw her pull her vibrator out of her drawer again and lie down on her bed.

When Gretchen spread her legs, all I could think of was how much I wanted to taste her young pussy before I fucked her brains out. Her pussy was facing the window which allowed me to get a perfect view of her performance. She ran the vibrator over her entire body, spending a lot of time on her nipples. I could see the look of lust on her face as she teased herself. She teased the inside of her thighs before running the vibrator over her pussy lips. I was slowly stroking myself while watching Gretchen's lewd solo sex show.

Before she inserted the vibrator into her pussy, Gretchen turned around and bent over, her curvaceous ass staring straight at me. Oh fuck, what I wouldn't have given to be in her room ready to fuck her doggie style. I wanted to hold onto her scrumptious butt cheeks while I drove myself into her. Instead, it was her plastic vibrating toy that was now buried in her. She feverishly worked the vibrator in and out of her pussy. I had to slow down on stroking myself in an attempt to postpone my orgasm for as long as I could.

Gretchen was obviously fantasizing about someone giving her a good hard fucking. In my mind, she was thinking of me. If that was true, how could I know for sure before I made my move to try and fuck her? I had to know for sure if it was just my hopeful imagination at work, or did Gretchen truly want to have sex with me. There was no doubt in my mind that I wanted to fuck her. I guess I had nothing to lose.

I watched closely as Gretchen turned onto her back. She then reinserted the vibrator into her pussy and used her other hand to massage her clit. I was concentrating on watching her solo masturbation scene unfold as it appeared that she was getting close to cumming. Her vibrator and hand were working her into a sexual frenzy, which had a similar effect on me.

Gretchen's body stiffened, her toes pointing straight, and she looked like she was wincing in pain. She was far from in pain, though, as her powerful orgasm rippled through her body, with mine coming shortly afterward. She brought herself to another one before the show was over for the night. Many things were going through my mind before I went to bed. She purposely raised her shade and turned on the light. She must have been hoping I'd be watching. It was a pretty lewd performance for a shy girl, but I told myself even shy girls must get horny. I was determined to form a strategy to see if Gretchen was open to fucking me.

Even though we exchanged text messages, Gretchen and I didn't see each other for a couple of days because we both had other things going on. That didn't stop me from jerking off while fantasizing about all of the things I wanted to do with her. She didn't put on any other performances for me, even though I kept checking to see if her bedroom window shade was open or not.

There was rain in the forecast for several days, and I wanted to get out of the house, so I sent Gretchen a text to see if she wanted to go to dinner.

She replied, "I'd love to. I wanted to go out to dinner, but I didn't want to go alone."

"Great, let's leave around 6."

"OK."

We then sent several texts trying to decide where to go. I felt like I was married again. We finally decided on a Mexican restaurant. I told her I'd order a rideshare in case we wanted to have a couple of drinks. She'd meet me at my house.

When Gretchen arrived, she was wearing a flirty, sleeveless, soft blue summer mini dress with a V-neck that showed some of her cleavage. She had her hair in a braided ponytail. She wore a pearl necklace and flip-flops.

I told her, "You look fantastic."

"You told me I should dress more fashionably, so I'm trying. I got this on sale."

"Wow. You have great taste. It looks great on you."

Her face reddened somewhat, and she replied, "Thank you. I'm glad you like it."

"Like it, I love it."

When our rideshare arrived, I opened the back door for Gretchen to get in first. She kept her knees close together, but her dress rode up, revealing more of her bare legs. She slid over so I could get in, and she started to tug the dress to cover her legs.

I told her, "Oh, don't cover them up. You have great legs."

Gretchen looked at me, smirked, and stopped tugging at her dress. When we arrived at the restaurant, it was difficult for her to get out of the backseat without opening her legs a little, and I got a quick peek at her floral-patterned white panties. My eyes were naturally drawn between her legs, and when I looked up, I saw her smiling at me. She must have known I was looking at her underwear.

Over dinner, Gretchen and I had a couple of Margaritas, which weren't that strong. I told her, "I'll make us some better ones once we get home if you want."

"Sure. You can teach me how to make them."

We had another nice conversation over dinner, and Gretchen looked lovely that night. She even wore some light makeup, which I'd never seen her wear before.

I told Gretchen, "You look beautiful tonight, and your dress is very sexy in a subtle kind of way. It also brings out the blue in your eyes."

It was obvious Gretchen wasn't used to receiving compliments on her looks and attire, and she replied, "Thank you. To be honest, no one's ever said that to me before. I feel kind of sexy, too."

"I'm glad you agreed to go to dinner with me."

"I'm glad you asked me to join you."

The waiter ruined the mood when he came to the table and asked, "How are you and your daughter enjoying your dinners?"

Gretchen looked at me, giggled, and replied, "Oh, I'm not his daughter. He's my boyfriend."

The waiter was embarrassed and stuttered his apologies. Gretchen and I were both holding back our laughter.

After he left the table, Gretchen said, "Did you see the look on his face? It was priceless."

"Yeah, he didn't know what to say."

After I paid the bill, I held Gretchen's hand as we left the restaurant, pretending to be boyfriend and girlfriend. The other customers were looking at us, and we saw some couples whispering to each other. We got a good laugh out of giving them something to gossip about.

When we got into our rideshare, Gretchen made no effort to keep her knees together as she got into the car, which afforded me another glimpse at her panties. She didn't try to tug her dress down to cover her legs like before. I thought I may have seen her pull it up another inch or two while trying to make it look accidental. I got a similar peek of her panties when she got out of the car.

I couldn't help but think, "I wonder if tonight's the night."

It was still raining outside, but it was warm, so we decided to have a Margarita out on the covered patio. I showed Gretchen how I made them, and she said it tasted much better than the one at the restaurant.

We started out talking about the recent run of rainy weather and her having to make a decision on which graduate school she wanted to attend next year. Gretchen then brought up the waiter in the restaurant.

"Do you think the waiter believed I was your girlfriend?"

"I don't know, but it was fun to see him squirm when you said that."

"I've never had a real boyfriend before."

"Never? That's a shame. Young guys are so stupid."

"Yeah, they're so immature. I was with one guy, but he just wanted one thing, if you know what I mean."

"I understand. Some guys are like that."

"I wish more guys were like you. You make me feel good about myself. No one's ever told me that I was beautiful or sexy before."

"You're very beautiful and sexy, Gretchen. You just need to have more confidence in yourself."

"That's easier said than done."

There was a definite sexual vibe in the air that night. I hoped it wasn't just me who was feeling that way. I was struggling whether I should try and fuck Gretchen though. Lord knows I wanted to, but I didn't want her to feel like I was using her just for sex. I also didn't want to scare her away because I was enjoying her company.

She then asked, "Can I have another Margarita? I want to make it this time."

"Sure, I'll supervise."

As we left the patio, we were exchanging glances. It was like we were both hoping the other person could read our minds. I think we were both feeling the same thing, but neither one of us wanted to be the first to say it out loud.

I was joking with Gretchen about how I was a bad influence on her by making a bartender out of her, and she replied, "I think I needed someone to bring me out of my shell and have some fun for once in my life."

"Well, if you're looking for a bad influence, I'm your guy."

I was helping her make the Margaritas, and at one point, I put my arm around her waist to reach around her. She turned and looked deep into my eyes, giving me an unmistakable look of lust. We both sort of stood there silently, looking at one another, and we both simultaneously tilted our heads, closed our eyes, and leaned forward to kiss one another. I felt like a bolt of lightning shot through my body, and she appeared to feel the same way. Gretchen turned around to face me as we kissed more passionately.

As we stood there in the kitchen, kissing one another, I thought to myself, "Well, it's now or never," and I slid my hand down her back to grasp her ass.

Grabbing a woman's ass is like the first test to see if she's open to going further. When I heard soft sighs coming from Gretchen, it gave me the green light to bring my hand up to cup her breast. In response, she pulled me closer to her. Our hips were now pressing against each other, making it impossible for her not to feel my erection.

When Gretchen reached down to slowly stroke my hard cock, I asked, "Are you sure you want to do this?"

"Absolutely, I've been thinking about this since that first night in your pool."

"Let's take this into the bedroom then."

Gretchen took my hand and said, "Let's go."

When we got to my bedroom, I told Gretchen, "Just so you know, I truly care about you."

"I know, Ray. That's why I'm here." She went on to say, "Just so you know, I'm not that experienced. I hope you won't be disappointed."

"There's no way I could be disappointed, Gretchen. You're so darn sexy."

The first thing I did was to remove her glasses, and I began to kiss her again. I could tell she was nervous, so I wanted to make sure I took my time. I also wanted to savor every second of making love to a woman more than half my age. She looked so angelic standing before me.

I ran my hand up her dress and found her panties soaking wet as I began to finger her through the silky material of her underwear. I could hear how wet and squishy she was. I ran my other hand up the back of her dress to fondle her meaty ass. I longed to get my hands on that ass and it was just as wonderful as I had imagined.

I then unzipped her dress and peeled it off her shoulders and down her torso, exposing her soft blue lace bra. More of her cleavage was revealed as I continued to strip her of her dress until she stepped out of it, leaving her in just her bra and panties. I could tell she was self-conscious about her exposed body. We began to kiss again as I fumbled with the hooks of her bra before taking a small step back to free her luscious breasts from their confinement.

"Your breasts are truly spectacular," I said as I gently squeezed them.

I leaned over to kiss, lick, and suck on her nipples. It was then time to remove her panties. I slipped my fingers inside the waistband and pulled them down. I got down on my knees to help Gretchen step out of them, leaving her completely naked. I got a close-up view of her hairy bush, and a faint whiff of her excited pussy. I kissed her lower abdomen and thighs and had her turn around so I could fondle and nibble on those pale white ass cheeks. I gave her a quick slap on the ass before I stood up..

Gretchen watched with lust in her eyes as I undressed. I don't have the greatest body, but I'm pretty well-toned. I have a thin coating of chest hair, which my previous lovers seemed to like. It's masculine enough, but I'm not some overly hairy guy either. I have medium brown hair with a touch of gray. I don't think Gretchen cared too much what my body looked like because I made her feel beautiful and sexy, and she truly was. Besides, her eyes were focused on my erection.

I went behind Gretchen and cupped her dazzling breasts and nuzzled her neck. I love to kiss and nibble on the nape of a woman's neck, and I know they enjoy it too. Her pleasure was my foremost focus. I wanted a much younger, inexperienced woman to have an intimate, joyous sexual evening, unlike her first encounter.

My dick was pressing between her fluffy buttocks and she wiggled her ass against it. After toying with her neck and breasts, my hands slid over her torso, up and down her thighs, around to her buttocks, and over to her back. I did this several times as she purred like a kitten to my tender touch.

I then laid Gretchen on the bed, where we began to kiss again. I ran my hand between her legs and I could feel the dampness of her pussy even before I inserted my finger. As my middle finger plunged into her, Gretchen began to thrust her hips upward and squirm.

It was then that I began to kiss, lick, and nibble my way down her body while touching and feeling every inch of her soft, bare skin. I spent a considerable amount of time focusing on her breasts and nipples to our mutual enjoyment. I jerked off several times dreaming of this moment, and I relished every second of touching and sucking on her hardened nipples.

I then made my way down her torso, passing by her pussy, and down each leg. I kissed each foot, and gently massaged them as I parted her legs to get a view of her hot pussy. I sucked on each toe before I made my way back up her leg. I spread her legs wide and began to lap at her juicy pussy which caused her to emit soft moans of pleasure.

I felt her body twitch as I teased her clit. I pushed her knees back towards her head, further exposing herself to me. I then dove in to tongue fuck her. Gretchen moaned louder and pulled my tongue deeper into her.

"Oh fuck, no one's ever licked my pussy before. It's better than I imagined. Don't stop."

"Oh, honey, you haven't seen anything yet, and I have no intention of stopping."

I tongued fucked Gretchen, devouring her ripe pussy like it was a gourmet meal. I then began to flick my tongue over her clit causing her to moan even louder. As she approached an orgasm, I finger fucked her and sucked on her clit. That pushed her over the edge.

"Oh god, I'm going to cum. Eat me, eat me, OOOOOHHHHHHH."

Gretchen was yelling for me to continue as she came to her first orgasm.

I was thinking, "Oh shit, she's a screamer."

There was nothing shy about her now. I was surprised when she flooded my mouth with her squirting juices. My late wife rarely squirted, but Gretchen was on fire that night. I let her recover for a short time. I also had to catch my breath before I continued eating her hairy pussy. She quickly came to a second powerful orgasm before she asked me to stop.

Her chest was heaving in an attempt to catch her breath when she said, "Okay, no more."

I knew I just gave my young neighbor an oral sex session she'd never forget. She was lying there with her arm over her forehead and her eyes closed.

When Gretchen opened her eyes, she looked at me with a wicked grin and said, "That was amazing. I've never cum like that before."

"I pride myself on satisfying my partner. Hopefully, it won't be the last time you cum like that."

I looked down at my erection and said, "Now it's your turn."

Gretchen swung around, took my dick in her hand and said, "I'm not very experienced giving blow jobs so please be patient with me."

"Don't worry, honey. I'll tell you just what I like."

Her mouth immediately engulfed my dick and she started to bob her head frantically.

I gently pulled her head off my cock and told her, "Slow down. Take your time. Use your tongue to lick my balls, lick my dick like a lollipop or ice cream cone, then take it between your lips."

"I'm sorry, Ray."

"You're fine, Gretchen. I'm just trying to tell you what guys like.

Gretchen followed my instructions and began to lick my balls and dick until I told her, "Now suck it."

She took my cock between her lips and started to slowly bob her head.

I wanted to give her some encouragement, so I said, "Oh, that feels good. Use your tongue, too."

I moaned softly as I felt her tongue swirl around my dick and said, "Oh yeah, just like that. Now, try and take it deeper."

Gretchen was now giving me a decent blow job and gagging a couple of times from trying to get it all into her mouth. She scraped me with her teeth once, and she apologized. I told her it was fine. It wasn't the best blow job I ever had, but there is no such thing as a bad one. I stopped her after several minutes because I didn't want to cum too soon. I laid her back on the bed and moved between her legs.

"I've been waiting for this moment for a while, Gretchen. You're so sexy."

"I've been thinking about doing this, too. Go slow, I've only done this once before, and it's been a while."

"I will, baby."

I rubbed my cock up and down against her wet slit a few times and said, "Tell me what you want me to do now, Gretchen."

"I want you to stick it in me."

"Stick what in you?"

"I want you to stick your dick in me. I want you to fuck me, Ray. Is that what you wanted to hear?"

"That's exactly what I wanted to hear, honey," I replied as I slowly slid my hard dick into her rarely fucked pussy.

Oh my goodness, did Gretchen have a tight pussy. She had only been fucked once before. She had more experience with vibrators than a dick. She wasn't a virgin, but she was pretty close to it. I could tell she was nervous, so I started to fuck her slowly. Once I saw that she relaxed and had a look of desire in her eyes, I started to move faster. I leaned forward to kiss her as I fucked her. There's nothing better than a youthful, tight pussy.

Gretchen began to move her hips upward to meet my thrusts and told me, "This feels sooo good, Ray. Don't stop."

"I wasn't planning on stopping," I said with a grin.

I was playing with and sucking on her nipples when I wasn't kissing her. I decided to pick up the pace, but I put her legs onto my shoulders. I was able to drive myself into her deeper and faster this way. She began to moan loudly and her tits were flopping around as I fucked that pussy hard and fast. Fucking a much younger woman is every older man's fantasy and I was living the dream that night.

I could feel my orgasm building and decided to take Gretchen doggie style. I saw her fuck herself that way with her vibrator and figured she'd like it too. Within seconds, she was bent over on my bed with her ass in the air, offering me her pussy. I got behind her, held onto those succulent buttocks of hers and drove my dick home.

Gretchen began to scream, "Oh yes, oh yes, oh yes," as I pummeled her from behind.

I grabbed onto her ponytail and began to lightly tug on it while slapping her ass with the other hand. Her ass cheeks rippled live waves in the water with each thrust and spank. She was screaming louder, too. She was so loud, I was afraid the neighbors on the other side might think I was hurting someone. In reality, I was giving a young woman the fucking she so desperately needed and wanted. I needed a good fucking too.

Gretchen was getting hotter the longer we fucked and cried out, "Oh shit, I'm cumming again."

My balls were about to burst too as they filled with cum. Shortly after Gretchen came, I grabbed hold of her ass, lunged forward, and thrust deep into her as I began to shoot my jizz into her. I was groaning myself because of how much and how long I've been wanting to fuck her. I never thought my fantasy would come true, but here I was, releasing my cum into that pussy I dreamed off.

When I was done, I collapsed onto her back and tried to catch my breath. I was breathing heavier than I do when working out at the gym. When my dick began to shrink, I withdrew from Gretchen and fell onto my back. She laid down face first on the bed.

When Gretchen rolled onto her back, she told me, "Oh my god, that was so good. Now I know why people like having sex so much."

"That was incredible, Gretchen. You're one hot lady."

"You're pretty hot yourself, Ray."

"I hope you don't have any regrets, Gretchen."

She scoffed at my comment and replied, "My only regret is not doing it with you sooner."

That sure was a boost to a middle-aged man's ego.

We both wanted to freshen up, so I let her use the master bath while I used the guest bathroom, and I told her I'd get us some water and fix us another Margarita. Gretchen joined me in the kitchen just as I was finishing up mixing our drinks. She was wearing one of my white V-neck T-shirts and looked sexier than ever. She had a certain glow about her, maybe it was that just-fucked look.

Gretchen's dark areola was quite visible through the thin cotton shirt, and her nipples poked through. The shirt came to just below her ass cheeks. When she dropped a napkin on the floor, she bent at the waist to pick it up. It was plain to see, she wasn't wearing any underwear. I gave her ass a playful slap.

She quickly stood up with a grin on her face and asked, "Hey, what was that for?"

"That's what you get for teasing me with that fine ass of yours."

Gretchen then lifted the back of the shirt to expose her ass and wiggled it, and asked, "Do you mean this ass?"

It was obvious she was feeling frisky, and when I moved towards her to spank her again, she began to laugh as I chased her into a corner of the kitchen. We were laughing as I pulled her away from the cabinets, lifted the shirt, and gave her a few quick slaps on her ass.

We stopped laughing and looked into each other's eyes. Our lips were naturally drawn to each other's, and we began to kiss passionately. She had her hands around my shoulders while I grasped her ass and pulled her closer.

Gretchen started to rub my dick, signaling to me that she wanted to fuck again. It has been a very long time since I've fucked a woman twice in one night but my dick was responding. I slipped my hand up the front of the shirt and began to finger fuck her as she leaned against the cabinet. I peeled the T-shirt over her head and removed my boxer briefs, leaving us both naked. I immediately began to suck on her tits again while she stroked my cock.

Gretchen then said, "Let's go back into the bedroom."

"That's a great idea," I replied.

I grabbed our drinks and then scampered off to the bedroom with my eager lover. You gotta love youthful enthusiasm.

By the time we got to the bedroom, I had lost some of my erection. Gretchen began to stroke me again, but I suggested, "Why don't you suck it again?"

"Alright."

I sat on the edge of the bed while Gretchen knelt before me. A guy feels dominant when he has a lady on her knees in front of him, ready to suck his dick. She took her time and licked and played with my balls, just like I taught her. She licked my shaft, playing with it with her tongue. Gretchen then concentrated her efforts on the head, licking it and sucking on it. I could tell she wasn't as nervous this time and was enjoying being on her knees giving me a blow job. Gretchen's head began to bob while she worked my dick over with her lips and tongue which caused me to moan softly. I could hear the sounds of her wet sloppy blow job as she sucked me.

I could tell that she desperately wanted to please me, so I complimented her on her efforts by saying, "Oh yeah, baby, just like that. You're doing great. Damn, your mouth feels good on my dick."

Gretchen sucked my dick for several minutes, and when she stopped to catch her breath, I said, "Here, get on my lap."

She smiled and quickly straddled me. She reached around to grasp my cock, aiming at her pussy. I could see the look of pure passion on her face as she lowered herself onto me. Gretchen then began to ride my dick, her amazing tits flopping in my face. I grabbed onto her fluffy ass while she rode me. Gretchen closed her eyes, bit her lower lip while the rhythmic sounds of her pleasure filled the room.

"Ah, ah, ah, ah."

When she would slow down, I'd suck on her precious nipples. As Gretchen was fucking me, she was moving her hips around while choosing her own pace. It appeared she liked being in control of her pleasure where she could direct my dick to just the right spot to scratch the sexual itch that had been building inside of her for a long time.

When Gretchen tired, I stood up without disengaging my dick from inside of her, turned her around, and began to fuck her. Her ass was on the edge of the bed while I stood with her legs resting on my shoulders. She began to feverishly massage her clit as I drilled her tight, tender pussy. I kept thinking how only one other man had his dick inside of her and I knew she was enjoying my fucking more than his.

Gretchen was squealing with pleasure and had another orgasm while my dick was pistoning into her as she came. After she recovered from her orgasm, I had her turn around so I could do her from behind again.

Before I reinserted my dick into Gretchen, I took a mental picture of her delectable ass bending over in front of me. I swore, I'd never forget seeing that gorgeous ass and hot pussy waiting for me. I took hold of her meaty buttocks and drove my dick home. I tugged on her ponytail and spanked her just like before. She seemed to like it, so I kept it up.

Gretchen was crying out, "Oh my god, your dick feels sooo good. Fuck me, Ray. Fuck meee."

As I was fucking her, I leaned over, and whispered in her ear while massaging her tits, " Your pussies mine now, Gretchen. It's all mine. Let me hear you say it."

"My pussy is yours, Ray. You can fuck me any time you want. You're so good. Fuck me, Fuck me, fuck me."

I started fucking her harder while I started to cum. Her pussy felt so good. I forgot how tight a young pussy was. She may have ruined me going forward. How could I fuck an older woman again after experiencing Gretchen?

After I withdrew from Gretchen, I knew I was spent. She milked my balls dry. She wanted to freshen up, and she asked me to get her a glass of water. By the time I got back from the bathroom and kitchen, my youthful lover was fast asleep in my bed. I covered her up, kissed her on the forehead, and joined her. I was exhausted too. That young girl wore me out.

It was strange sharing my bed with someone else. No one slept in my bed with me for several years. I was smiling to myself before I fell asleep. I had a naked twenty-one-year-old woman in my bed. It was a great boost to my ego to know I could still sexually satisfy her at my age. Maybe the old guy still had it.

From that illustrious night until Gretchen's parents returned, we hooked up several times a week. That night was a sexual awakening for her, and lit a fire in her loins as well as mine. It had been a long time since I got laid regularly.

There were several days when Gretchen and I couldn't fuck because she had her period, but she used it as an opportunity to refine her cocksucking skills. We were having dinner at my house when she broke the news that she'd be out of action for a few days.

I half-jokingly commented, "That doesn't mean you can't give me a blow job."

I was pleasantly surprised when she said, "Okay. I could do that."

We began to makeout on the sofa and I took off her shirt and bra so I could play with her tits. She was stroking my dick and then helped me take off my shorts and underwear. She had sucked my dick plenty of times by then but still hadn't deep throated me. She seemed determined to keep trying and I wasn't going to complain.

Gretchen's mouth and tongue felt wonderful around my dick and she was quickly becoming an expert cocksucker. She liked giving me wet, sloppy ones, too. I was playing with her tits while she sucked me. I kept looking down at her head bobbing in my lap, in disbelief at my good fortune.

I warned Gretchen, "I'm about to cum," but she never lifted her head.

Apparently, she wanted to discover what a man's cum tasted like, and I wasn't going to stop her. Even though she knew I was going to cum, she was still caught off guard by the amount I was squirting into her mouth. Gretchen took the first wad but gagged on the next couple. There's no way I could stop myself now so more cum kept flowing into her mouth.

She pulled my dick out of her mouth for a moment. She coughed and some jizz dripped out of her mouth and down her chin. Her face was still close to my dick and I shot a couple of wads onto her forehead and cheek. Gretchen quickly covered my spurting cock with her mouth and swallowed the rest of my load.

When Gretchen lifted her head, she looked so divine with my cum dripping from her face and I said, "That was an outstanding blow job."

"Thanks, I'm glad you liked it."

"How was your first taste of cum?"

"Uh, it wasn't bad. I mean, it wasn't great either. I don't see what the big deal is for some women."

Gretchen gave me a couple more blow jobs before her period ended. She even deep-throated me, a feat she was proud to accomplish.

I was thinking, "Damn, this girl has come a long way in a few weeks."

The crème de la crème came a week before Gretchen's parents returned from their trip, and she would be going back to college. I had increasingly begun to play with her ass whenever I fucked her from behind. I first began to touch her asshole which led to me eventually working my finger into it. She didn't seem to mind, so I continued it each time I had her bent over.

One night, we were naked in the hot tub, talking about how she had not only broken out of her shell but had shattered it. Gretchen began to dress in more fashionable clothing; she was now wearing contact lenses after ditching her glasses, we would skinny dip regularly, and she had become very sexually experienced under my tutelage. She would jokingly refer to me as "Professor."

While having some wine in the hot tub that night, Gretchen asked me, "Is there anything else you'd like to teach me, professor?"

"Well, there is one more thing that I think we should try?"

"What's that?"

"You know how much I love your ass. I was thinking maybe we could try doing anal before you leave. I mean, if you're trying to get an A in this class, it would be nice. Think of it like a final exam," I replied with a devilish grin.

Gretchen pretended to be contemplating my suggestion, and then replied, "I don't know. I've heard it can be quite painful. On the other hand, I am carrying a 4.0 GPA. I wouldn't want to ruin my perfect record."

"The secret is, my dear, to have an experienced lover who will take his time and use plenty of lubrication."

Gretchen teased me by asking, "I don't suppose you know someone with those qualifications, do you?"

"Well, it just so happens, I have experience and have some lube in the bedroom," I replied with a grin.

I was getting an erection just thinking about the prospect of having Gretchen bent over on my bed offering to let me stick my dick into that precious ass of hers, the one I've cherished since I first saw her in a bathing suit. I dreamt of having that puckered hole staring at me while I gradually inserted my dick into her.

"I guess now is as good a time as any," Gretchen said.

"It sounds good to me. Let's go."

We dried off our naked bodies under the stars and moon. I let Gretchen walk ahead of me into the house. I was watching her pillowy ass twitch and wiggle the entire time. I grabbed another bottle of wine and headed to the bedroom.

When we got to the bedroom, we began to kiss while our hands explored one another's familiar bodies. I sucked on her nipples while sinking my fingers into buttocks, kneading them like bread dough. My middle finger massaged her asshole but I didn't penetrate her just yet. I wanted to take my time to allow her to relax at the thought of being sodomized by me.

I then suggested, "Why don't we have sixty-nine? You like doing that."

"Sure, but I thought, you know, you wanted to do my butt."

"Oh, I will. I told you, I'd take my time. There's no rush."

I had Gretchen straddle my head which gave me perfect access to those doughy butt cheeks of her and her asshole was looking back at me while I ate her pussy. I wanted to make sure Gretchen was nice and hot before we carried on with the evening's activities.

The first thing I did was to firmly grasp her cheeks and nibble on them in the process. I then began to run my tongue along her slick slit, tasting those tangy juices of her pussy. I kept groping her ass the entire time. Meanwhile, I felt her lips and tongue on my balls and dick.

When I began to tongue fuck Gretchen my upper lip accidentally came in contact with her asshole. We had just gotten out of a chlorinated hot tub, so I knew she was clean. I heard her moan softly and wiggle her butt in my face. My lip came in contact with her asshole a few more times with her moaning each time. I got an uncontrollable urge to swipe my tongue along it, which made Gretchen moan even louder.

I figured, "If she likes it, I might as well continue," so I alternated between licking and tongue fucking her pussy to licking her ass.

If she liked it, it would only make it easier for me to stick my dick up there later on. Gretchen was squirming on my face, rubbing her pussy and ass against my mouth and tongue. I began to flick my tongue against her clit which made her moan even louder. She was having a difficult time blowing me because of all the pleasure she was receiving. That didn't concern me because I wanted to save my excitement for when I fucked her ass.

When I sensed she was close to cumming, I concentrated on her clit which brought her to a nice juicy orgasm. I eagerly lapped at her pussy until she regained her composure.

I then asked, "Are you ready to try anal?"

"I guess I'm as ready as I'll ever be."

Having given me the okay to proceed, Gretchen climbed off of me and assumed the position of getting on all fours with her head on the mattress and her ass high in the air. As I was getting ready to grease her up, she teasingly wiggled her ass. I leaned over to kiss her cheeks and lick that puckered hole of hers.

I then dripped some lube on her asshole which caused her to say, "Oh, that's cold."

"Don't worry, honey, it'll heat up in no time."

I rubbed the lube around her asshole and slowly inserted my finger. She clenched her ass for a moment and when I felt her release her grip on my finger, I began to move it in and out of her. When I felt her relax even more, I dripped more lube onto her and inserted a second finger. Once again, she clenched her ass. I waited before finger fucking her with two fingers. Gretchen seemed to be enjoying the feeling of my fingers, so I kept it up for a couple of minutes.

I then asked, "Are you ready for me to continue?"

"I guess so."

I generously applied the lube to my hard cock and dripped a little more onto her asshole. I got behind her, slapped her ass, and felt my dick touch her butt hole. I held my dick in place with one hand and held onto her ass with the other. I began to gently push forward. Gretchen got nervous and clenched up when I inserted the tip of my dick into her.

"Relax, Gretchen. You'll be fine."

"That's easy for you to say, no one's sticking their dick up your ass," she replied with a nervous giggle.

When she relaxed a little, I pushed further into her. I stopped when she clenched up again. I waited a few seconds and pushed forward again.

I told Gretchen, "The head of my dick is in there. How are you doing?"

"I'm okay, just go slow."

I pushed in deeper until I heard her cry out, "Ow, ow, ow, stop, it hurts."

Gretchen was breathing faster as she dealt with the pain. I waited patiently until she said, "Okay, keep going."

When I was about half way in, I began to very, very slowly thrust in and out of her ass. I'd go a touch deeper with each forward movement. She'd stop me, at times, and I would wait until she told me it was okay to proceed.

When my cock was fully embedded in her ass, I told her, "There it is, honey. You have it all in your ass now. How are you doing?"

"I'm good, just go slow."

I began to slowly fuck Gretchen's tight virgin ass. I had both hands on her buttocks as I thrust in and out of her. I was honored that she allowed me to be the first man to sodomize her. She trusted me. I kept moving slowly so I didn't hurt her and break her faith in me. I thought her pussy was tight, but her asshole was even tighter.

When I saw her reach between her legs to rub her clit, I knew she was beginning to enjoy having a dick in her ass and began to fuck her faster. Gretchen then began to push back against my dick while breathing harder and rubbing her clit faster.

I thought to myself, "Um, she's liking this."

Gretchen asked me, "Do you like fucking my ass, Ray?"

"I love fucking this fine ass of yours, Gretchen. It's awesome. Do you like it?"

"It's better than I thought it would be. I feel so naughty. Oh yeah, fuck my ass, Ray."

"You're such a bad girl, a bad girl with a nice ass," I told her and began to spank her.

She started to rub her clit faster, and breathe harder while crying out, "I'm so bad, so bad. Fuck my ass. Fuck it."

Gretchen started to cum and I wasn't far behind. I tried to hold out as long as I could. I wanted to keep fucking her big, tight ass all night but I couldn't hold back any longer. My dick began to pulsate, I grunted loudly, and I thrust deep into my young lover's asshole as I shot my load deep into her bowels.

We both fell onto the bed with my dick still embedded in her ass. After I caught my breath, I withdrew from Gretchen's backside and got towels to clean ourselves up.

"That was incredible, Gretchen. That fine ass of yours was made to be fucked. It seemed like you enjoyed it too."

"It was good once I got used to having you in my butt. The best part was knowing how much you were enjoying it. I wanted to please you."

"Mission accomplished, babe. These last few weeks have been amazing. Sadly, you'll be leaving soon."

"You've helped me release a side of myself that I didn't have the guts to explore. You made me feel confident and sexy."

"I've noticed the change in you, too, Gretchen. You didn't appreciate how beautiful you truly are."

With only a week left before her parents were returning, Gretchen and I decided to make the most of it. We spent a lot of time having sex and I even fucked her in her parents bed. It was something she wanted to do. Maybe it was her way of rebelling from a strict upbringing, but who was I to question it? I didn't care, I was having the time of my middle-aged life with a much younger woman.

My only problem was keeping up with her sexual desires. I had to make sure I stayed hydrated because she was draining my balls dry to the point where they hurt a little bit. I found that the more I had sex, the more semen I was able to produce. It also helped being around a lovely woman who made me feel sexy and desirable. It wasn't just a one-way street.

On the night before her parents would be coming home, I treated Gretchen to dinner at a five-star restaurant. She wore a flirty summer dress that showed more cleavage than I'd ever thought she would wear. She looked classy but sexy. She put a little curl in her hair, had on some light makeup, and was wearing a pair of nude thigh-high stockings.

It was a bittersweet evening because we knew it would probably be our last one together for a long time, and who knew if we'd ever get together again. If we never had sex with each other ever again, we'd still have great memories of how we found companionship that summer and had some of the best sex we'd ever have.

Before we got in the car, I told Gretchen, "I can't wait to get you home after dinner because I'm going to fuck you til you can't walk straight."

"Oh yeah, maybe I'm going to fuck you til you can't walk straight."

During dinner, she told me, "I can't wait to suck your dick."

"Um, I can't wait to eat that tasty pussy of yours."

Later on she said to me, "My pussy is hot already at the thought of what we're going to do when we get back to your place."

"I can't wait either. You're like a drug that I can't get enough of."

Gretchen kicked off her high heels and ran her foot along my leg under the table. Seeing and feeling her stocking-covered toes against my leg drove me wild, and she knew it. She kept giving me these sassy smirks because she knew she was teasing the fuck outta me.

I told Gretchen, "You're a fucking cocktease."

She replied, "No, I'm not. I fully intend to finish what I'm starting."

"Wow, you've come a long way from being that shy young woman at the start of the summer."

"Yeah, she's long gone now. See what you've done to me," Gretchen replied with a grin.

I smiled back and said, "You're welcome."

We decided to skip dessert when Gretchen told me, "I'll be your dessert tonight."

"That's fine by me because that sweet pussy of yours is all I need."

We couldn't even wait until we got home to start our night of passion. We were making out in the parking lot before I even opened the car door for my date. Our hands were all over each other. Gretchen gave me an erection in no time and I was fingering her pussy through her thong.

Gretchen continued to stroke me when we got into the car. She pulled my zipper down and released my hard cock from the confines of my underwear. Her mouth quickly replaced her hand as she started blowing me in the parking lot. I was looking around to see if anyone was walking by, but Gretchen didn't seem to care.

She lifted her head and said, "Go ahead and drive home," and went back to sucking my dick.

I started the car and began to drive. It was extremely distracting to try and drive while getting a blow job, but it was also exhilarating to be part of something so daring. Most people in the other vehicles had no idea what was happening, but a few saw Gretchen's head bobbing in my lap. One trucker got a birds eye view of her sucking my dick but it didn't stop her.

She told me to keep driving while she blew me. However, when I felt I couldn't hold out any longer, I pulled into a remote area of a shopping center parking lot. I was afraid I'd get into an accident if I continued to drive while cumming. It's a good thing, too because I closed my eyes, gently held her head, and gave her a nice load of my creamy jizz that she lapped up and swallowed without spilling a drop.

After Gretchen sucked me dry, she lifted her head, and said, "Take me back to your place. I'm so fucking hot right now."

I zipped up my pants, and we were outta there. On the way home, she lifted the hem of her dress and was rubbing her pussy through her thong. When we got to my house, we started stripping off our clothes as soon as I shut the door. I grabbed a bottle of wine and a couple of glasses as we scurried off to the bedroom.

I didn't waste any time kissing, licking, nibbling, and sucking on every inch of Gretchen's body. I knew this was probably our last night together and was in no rush. She already sucked my dick so I needed some time before I'd be ready again anyway.

I kissed those soft lips of hers, nibbled on her ear lobes, nuzzled her neck, left a hickey on both breasts, and feasted on those hard, dark nipples of hers. I kissed and licked her torso and tongued her navel. I worked my way down each leg and massaged the soles of her feet while sucking on her toes. I turned her over and worked my way up the back of her legs before kissing, nibbling, and tonguing her ass. Gretchen was moaning the entire time I was playing with her luscious body.

There are times when a guy sees a young lady and thinks, "I would love to lick her all over and fuck the shit outta her."

Well, I had been living out that fantasy for weeks. I was acting as a sexual mentor for a formerly shy, inexperienced woman. She was now confident in her sexuality, and I was the beneficiary of her newfound self-esteem. A confident woman oozes sexuality, and there's nothing better than an enthusiastic sexual partner. We found a sexual compatibility with each other; we were in sync in our attraction and expectations.

It was Gretchen who then suggested, "Let's sixty-nine. I like doing that."

"That's an offer no man will refuse."

I ate that pussy and savored the tangy taste and smell like it was my last meal. While I was feasting on her pussy, Gretchen was licking and sucking my dick back to life. She was so turned on, it didn't take long for her to have her first orgasm. Maybe it was because I didn't know if or when we'd be together again, but Gretchen's pussy seemed to taste even more delicious that night. I ate her to a second body-shaking orgasm.

After she caught her breath, Gretchen told me, "You can fuck my ass if you want."

"Of course I want to."

I prepped her ass with plenty of KY jelly and applied a generous amount to my dick too. Gretchen wasn't nervous at all, which made it better for both of us. She knew she could easily accommodate my dick in her ass now.

She didn't flinch when I pressed my dick against her asshole and effortlessly slid it in. I think she enjoyed taking it up the ass but she also knew it was a special treat to let a guy sodomize her. It was like her going-away gift to me that I happily accepted. If there is one thing about her body that I adored most, it was her ample ass and jiggly buttocks. I knew she wasn't uncomfortable so I tore into that fine ass of hers. I'd look down to see my dick sawing in and out of her little brown, puckered hole. She looked divine bent over like that.

How many times have you seen a lovely lady in short shorts, leggings, or tight jeans and thought, "Damn, she's got a nice ass. I'd love to get my dick in there."

Well, I had Gretchen bent over taking my dick in her ass, just like I had always wanted. It wasn't the first time, but it might be the last time with her. I had cum earlier from her blow job so I was able to fuck that tight ass for a lot longer than I normally would have. I relished the feeling of her meaty ass cheeks while having my dick buried deep inside her backside. Her ass was made for fucking and I was the first man to experience the pleasure of her offering it to me.

I must have fucked her butt for at least half and hour before I came. After my orgasm, I kept my dick in her ass until it softened. I never wanted to withdraw. I gave her butt a quick spanking while I watched those lovely cheeks jiggle. We laid in bed for several minutes reflecting on how we had grown so close.

"I can't believe how much my life has changed in the past several weeks, Ray. I was always too busy studying to enjoy myself. I've had so much fun with you."

"You certainly livened up my boring life. I'm going to miss you, Gretchen."

"I'm going to miss you, too, Ray. If you're up for more fun. It's our last night together, we should make the most of it."

"I don't know how much I have left in the tank, but I'm game for anything."

We decided to take a shower to freshen up. It also gave me time to take a pill to help me get another erection. I'm not a young man anymore. I don't know if I needed a boost from a pill, but I didn't want to take any chances.

It was fun to shower with Gretchen and use the body wash to slide my hands all over her tender body. She looked so angelic as the warm water cascaded over her curvaceous body. I washed her entire body from the neck down to her pretty little toes for her. Her skin was so soft and alluring, and I cherished every second of being able to gently caress her succulent body.

Gretchen took her time to wash my body, also. We were kissing and making out while the warm water flowed over our naked bodies. I was sucking on her nipples and finger fucking her while she was stroking my cock, trying to bring it back to life.

We stayed in the shower until the water started to chill, and we then helped to dry each other's bodies. It was then that my dick started to grow harder. Once we were dry, we retreated to the bedroom where Gretchen got on her knees before me and began to suck my dick. She had become an expert cocksucker under my tutelage over the past several weeks. They say practice makes perfect, and she had tons of practice.

It wasn't long before my dick was hard again. It was obvious that Gretchen was not only good at sucking a cock but she enjoyed doing it as well. A guy can tell if their partner is going through the motions or if they are blowing you with enthusiasm. Enthusiasm is the difference maker between a good blow job and a great one. Gretchen was giving me a great blow job.

She then pushed me onto the bed and said, "I'm going to fuck you now."

I just grinned as she climbed on board and began to ride me. She looked heavenly while riding me. Gretchen would lean over and present her breasts to my lips so I could suck her nipples or she would kiss me deeply while her vice-like pussy engulfed my cock.

When she began to tire, Gretchen turned around and straddled my face. I immediately began to lick that soaking wet pussy as she sucked my dick again. At times, she would sit up straight and rub her pussy and clit along my lips and tongue before going back to blowing me. I ate her pussy until she came as her pussy juices flowed onto my tongue.

It was my turn to take charge and I fucked her doggie style for several minutes before turning her around in the missionary position. We must have fucked for at least forty-five minutes. Part of me wondered if I had any cum left in my balls but I eventually felt my orgasm approaching.

I wanted to gaze at her youthful face as I came in her one last time while she coaxed me on by saying, "Cum for me, Ray. I want to feel you cum in me. I want to please you."

I released what cum I had left in my balls. It wasn't as much as the first two times, but it still felt amazing. Since Gretchen and I first hooked up, I've had the best sex of my life, and there is no doubt she did too. We both knew our summer relationship had come to a climax. I went to the bathroom to grab us both a towel and went to lock up the house. When I came back, Gretchen was fast asleep in my bed, which was fairly common as of late.

Gretchen was up fairly early the next morning and was getting dressed when I asked her if she wanted breakfast.

"No, I have some things I need to take care of before my parents get back." She went on to say, "I have to spend some time with my parents and other family members. I don't know if I can see you again. I don't want them to get suspicious of, you know, what we've been doing."

She was trying to gently tell me, "I can't fuck you anymore," but I already knew that. I didn't need or want any drama with her parents either. The last thing I needed was to try and explain why I was fucking their twenty one year old daughter almost the entire time they were gone. It seemed so taboo to be fucking my neighbor's daughter but that's what made it so much fun too.

Before she left, Gretchen told me, "I'll see you before I go, but it won't be for long."

"I understand."

She kissed me before she left, and that's where we left it. Over the next few days, I saw Gretchen coming and going with her parents. It was killing me not to be with her. She was so close but yet so far away. We were text messaging each other, saying how much we missed one another. In my heart, I was hoping for one more encounter with Gretchen.

On the morning that she was leaving, I got a text from Gretchen that read, "I told my parents I have to say goodbye to you before I leave. I'll be there in a few minutes."

"I'll be here waiting for you."

When Gretchen arrived, she was wearing a very conservative top that hid her breasts and an over-the-knee skirt. I assumed she was dressed this way for her parents' benefit.

She told me, "I don't have long."

"I understand."

"I just wanted to thank you for all you've done, Ray. I'm going to miss you."

"I'm going to miss you, too, Gretchen. You've done a lot for me as well."

We gave each other a short kiss that turned into a more passionate one. Gretchen sighed when I cupped her breasts, which led to us kissing again. She moaned when I slid my hand up her skirt to rub my fingers along her pussy through her panties.

"Please don't, Ray. I have to go."

Her soft moans told me otherwise as I pushed the fabric of her panties into her pussy and began to massage her clit with my thumb. She began to moan louder, and I could feel her panties getting damp.

"No, Ray. Not now. My parents are waiting for me."

"Let them wait."

I pushed her panties aside and continued to finger fuck her and massage her clit. Gretchen was pleading with me to stop, but her body told me differently. Her breathing got heavier as I continued to play with her pussy. I knew that familiar sound of her increased excitement and knew an orgasm wasn't far behind. Within the next minute, Gretchen had an orgasm right there in my living room. I opened my shorts and pulled them off along with my boxer briefs, and pressed down on her shoulders.

Gretchen's eyes were telling me, "I shouldn't be doing this. My parents will wonder about me," but that didn't stop her from dropping to her knees. I knew she couldn't resist my dick.

She took my dick in her mouth and began to blow me. It felt so wrong to be coercing her into one last sexual encounter, but that's why it was so exciting. I had her blow me for a little while, then I bent her over the side of the sofa, ripped her panties off, and shoved my dick into her hot pussy one last time.

I pummeled that pussy hard and fast, causing her to say, "Oh shit, Ray. Fuck me, fuck meee. I'm going to miss your dick. I really am."

"I'm going to miss your tight pussy too, Gretchen."

Gretchen had another orgasm just before I filled her pussy with my cum. I then made her get on her knees and lick me clean.

Just as she was finishing, her phone buzzed, and Gretchen said, "It's my parents. I have to go."

We hugged and kissed one more time. We both were fighting back the tears as she walked out the door.

Gretchen turned to me as she was walking away and said, "I'll be back for the Thanksgiving break."

"I can't wait. You know where to find me."