Samantha changed my life Ch. 11

I have known Samantha for years. My late wife Ann and I met her when she first became a bartender at a local upscale diner. Ann and I were both sexually attracted to her, but decided the age discrepancy was too much. But, in the meantime, my wife and Samantha became good friends. My wife was a mentor and confidant to her. Samantha was very broken up when Ann died. After Ann passed, my attraction to Samantha increased.

We stayed in touch, but I had some awkward moments because my attraction for her kept increasing. More than 4 years after Ann died, I steeled myself up and decided to ask her out. She surprised me by saying yes.

She works in restaurants, so I invited her for a home cooked meal. I made a delicious dinner, created a great atmosphere and we had a good time. After dinner, we started kissing and our temperatures rose rapidly. We ended up in bed and had incredible sex. Afterwards, she ended up making me cum a second time sucking my cock in the living room. We had great conversations, good food and great sex. She agreed to spend the night.

The previous chapter summaries have been getting long. The story of my May/ December fantasy relationship has been a great story to write. If this is the first time you're reading the story, please read the earlier chapters first.

I'm Bob. I'm a 64-year-old male who retired earlier this year from a career in technology. I'm 5'10, in good shape but feel like I could lose 10 or 20 pounds. I have salt and pepper hair and bright blue eyes. I think I'm average looking, but many women have told me I'm handsome. Personally, I think my sense of humor outweighs my looks.

Samantha is 28 and is 5'7" with luscious "D" tits, a curvy figure, slender hips but a fantastic ass. She has amazingly toned legs with nice thighs and well-defined calves. She is incredibly smart, wise beyond her years and is very funny in addition to being smoking hot. She has brown shoulder length hair, a beautiful face and wears very sexy librarian glasses.

After Samantha left, I did some work in my office and some chores around the house. Samantha called me on her way to work and we chatted for a couple of minutes. She reminded me that she was going to come over after work.

Before dinner, Amy called me. She thanked me again for dinner and said, "you both looked really happy being together. How's it going?"

I replied that, "I'm doing great, feeling very happy right now." I continued "I haven't felt this good since Ann died. We're going to the farmer's market tomorrow, and it feels good doing everyday ordinary things with her." As I gave it some thought, I said, "I feel way closer and more connected to Samantha than I ever did with Laura."

I thanked her and Jon for making Samantha comfortable with all of us, she relaxed and had a great time.

I had leftover Chicken Divan for dinner and ate on the porch watching the ball game. It was a beautiful evening, and I stayed on the porch having a glass of wine until the news came on. I was looking forward to seeing her tonight. I made it a point to lock the door and head up before Samantha got home. I left the light on in the kitchen and went upstairs to watch TV and wait for her.

Fridays are always busy at Tradewinds. It was almost 1 when she came upstairs. I was sitting on the bed watching TV, I stood up and walked to her. She put her arms around my neck, and I wrapped my arms around her waist as we kissed.

"Did you enjoy using YOUR key to come in?" I asked with a smile on my face.

Samantha laughed and said, "I was surprised the door was locked and had honestly forgotten about my key for a second. Then I remembered it and unlocked it, and saw lights were on so I could get to the stairs. You did that on purpose!"

Still smiling, I said, "I couldn't help myself."

Samantha replied, "I love you, and I love having 'my' key and 'my' dresser and 'our bed' here with you!"

Samantha stripped down and got in bed. I took off the shorts and T-shirt I was wearing and got in bed with her. We talked for a few minutes about her shift. The volume was low on the TV and we snuggled together. Within a couple of minutes, Samantha had fallen asleep, snoring softly next to me. A few minutes later I shut off the TV and fell asleep snuggling with Samantha.

I woke up the next morning a little after 9. The bed was empty and the bathroom door was closed. Samantha came out in a couple of minutes. She gave me a kiss and told me she was going down to make coffee. I went to the bathroom and sat on the headboard, waiting for her to come back.

She came into the bedroom with two cups of coffee. She handed me one and sat down next to me. She was wearing her sexy white fluffy robe, and my cock was definitely responding.

We sipped our coffee and Samantha chatted some more about last night's shift.

After I finished my coffee, Samantha peeled off her robe and got on her knees between my legs. My cock had already started to harden. She rubbed a stiff nipple over my cock and then lowered her mouth onto me.

My cock instantly responded to the smoothness of her mouth and the feel of her tongue. As I hardened in her mouth, she moaned. Once I was fully erect, she pulled me out of her mouth. "I love it when you get hard in my mouth!" she exclaimed. She lowered her head again and began bobbing up and down, swirling her tongue over the head, looking me in the eye the whole time.

I moaned as she expertly sucked my cock. She had one hand wrapped around the base of my cock and the other fondled my balls.

She could feel my balls starting to tighten. She lifted her head off my cock and I gasped, "Sweetie, I'm so close!"

She looked at me with a grin and said, "I know." She then pressed the tip of her tongue against my cock and licked her way down to my balls.

She pulled one of my testicles into her mouth, swirling it with her tongue while I moaned out loud. She gently pressed her teeth against it. I exclaimed, "oh, FUCK, that feels incredible!" She let go of that testicle and took the other in her mouth and repeated the treatment.

She slid her mouth off of my balls and licked her way back up to the head of my cock. She slipped her mouth over the head and started twirling her tongue around the head while her hand stroked the rest of it.

In a minute or two I exclaimed, "I'm about to CUM!" Samantha pulled back and barely had the tip of my head in her mouth as I unleashed into her mouth. I shot three or four strong spurts into her mouth.

She lifted her head off my cock and moved up next to me. She pushed her lips on mine and pushed her tongue in my mouth. She still had most of my load in her mouth and shared it with me. I enjoyed it as she snowballed it into my mouth, tasting myself.

After we kissed and snuggled for a minute, she murmured, "I can't wait to watch you suck a cock in front of me!"

That excited me a great deal. I found out after Ann died that I didn't enjoy it nearly as much without a woman there to watch, so I hadn't done it since 8 or 9 months after she passed, but I did meet with a couple about a month before I started dating Laura. Laura was WAY too vanilla to bring up the idea of a threesome.

I replied that, "I'm very excited by that, I have a couple of ideas in mind."

"Really!" she replied.

"Do you remember Joe, the server at Steak 47?" She nodded. "Ann and I had several threesomes with him before COVID. Just as we were comfortable enough to think about picking that back up is when Ann got diagnosed. If you're interested, I could give him a call."

Joe was taller than me, at least six feet, about 10 years younger than me, was handsome and athletic with salt and pepper hair and a matching beard. I could see Samantha pondering.

She said, "yeah, you know him, you've done that before with him. It won't make you uncomfortable that you've been with him with Ann before?" I shook my head no.

She approved, "OK, that would work for me too!"

I replied that I'll call him and see if he's interested.

She jumped out of bed and said, "let's get in the shower."

I protested and said, "I want to take care of you!"

She smiled at me and said, "I have cum so much in the last month, it didn't even occur to me. I just wanted to give you a nice morning blowjob. I'm much more interested in getting some breakfast and going to the farmer's market!"

I laughed, and we jumped in the shower. Afterwards, we dried off and got dressed and headed down to Americana. Before we left, I threw her uniform in the laundry, so she didn't have to rush home for a fresh one before work.

It was a little after 10:30 when we came in and automatically went to the bar. Diane was the weekend day bartender. She was another of Samantha's friends, who had been on last weekend's girls' night, and was still setting up.

Samantha said, "Hi Diane, I know the bar doesn't open 'til 11, but can we sit here, or do you want us to get a table?" I knew her a little bit, I used to bring my stepmom in for Sunday brunch every week or two before she passed.

Diane smiled brightly, and said, "no, go ahead and sit down. I think I can handle the two of you while I finish setting up!" Diane's smile got bigger and she continued, "Hi Bob, it's good to see you, it's been a while. You two look really good together!"

We sat down and ordered two Stoli Bloody Marys. While Diane made them, Samantha leaned up off her bar stool and grabbed a couple of menus from over the bar.

We looked it over and both decided on our breakfast orders. Diane took our orders and continued opening up the bar.

Samantha put her hand on mine, and said, "my mom wants to have lunch or dinner with us. She didn't mention whether my dad was going to be with her. What do you think?"

I looked at Samantha and said, "I actually met them both, two or three years ago, when you had a birthday dinner here. I want them to be comfortable with us, so yeah, let's do that with either her or both of them."

"Oh, I forgot about that! OK, do you want to do lunch or dinner?" I replied, "whatever works for both of you."

Samantha replied, "I'll work it out with her. I thought I would be nervous about you meeting them, but I'm really not. I think you and I are doing great, and I feel so comfortable with you. They are going to have to learn that we are a great couple and fit each other perfectly."

I smiled and agreed with her. I reminded her that I wanted to go away for a long weekend. It was mid-July and I knew she typically needed to schedule time off in advance. She replied that she would talk to her manager about it tonight.

After we ate, we headed a couple of towns over to the farmer's market. Southern New Jersey has some charming smaller towns with great "downtown" areas. This was one of those towns, so we browsed around the farmers market and spent the afternoon browsing the shops up and down the main street. For me, it all felt so comfortable and ordinary and I was at complete peace. We were usually hand-in-hand and kissed a few times. We received a lot of looks from people when we were affectionate.

We got home around 4. I put her uniform in the dryer and another load of laundry in the washing machine.

I came back into the living room, and Samantha was on the phone. In less than a minute it was obvious that she was talking to her mom. She said she loved her and hung up. She looked at me and said, "Dinner on Monday night?"

"That's fine" I said. "Why don't we go to Mantua Inn? It has good food and it's quiet."

She agreed and said, "plus, it's almost exactly halfway between here and their house." She smiled and said, "neutral ground!"

I told Samantha that it was where Jon and I had our infamous single site pub crawl. Jon's day job was as a banker, and we met for lunch at the Mantua Inn on Presidents Day. Around 6, Ann called me, we were still there. I wasn't hammered, but I could definitely use a ride, so I invited her to come for dinner, and Jon called Amy. When they arrived, the bartender assured both of them that we had plenty to eat and drank pretty moderately.

Our long-time congressman had recently resigned, and Jon and I spent a lot of time talking about him running for the seat. When we explained it to them, the whole bar cheered, "Jon for Congress!"

Samantha laughed at the story. She asked if he ran for Congress. I replied, "no, Amy was dead set against letting him do that. She can be introverted and is very private."

Samantha grabbed her uniform out of the dryer and changed. She asked, "can I come over after work? Allie is spending the weekend with her new boyfriend, and I would much rather be snuggled up with you tonight!"

I smiled and said, "Absolutely!"

She leaned in to kiss me. When she pulled back, she grinned and said, "good, I'll count on you for that orgasm you wanted to give me this morning!"

I laughed in response as she headed out the door to leave for work, both of us saying we loved each other.

I was pretty sure Joe worked both weekend nights at Steak 47, so I texted him and asked him to give me a call when he had a minute.

I spent the rest of the afternoon cleaning the house and doing some laundry. Around 7, I made some dinner and ate on the back porch, watching the ball game.

Joe texted me back around 9 and said he would call me tomorrow afternoon.

I was still on the porch, watching TV and sipping a drink when Samantha pulled into the driveway a little after midnight. I stood up as she walked up the steps and we kissed.

"You're home early!" She replied, "it pretty much died by 10:30. I did most of the closing early, and the place was empty at 11:30. We were all out of there less than ten minutes later."

We walked inside, I asked, "do you want a drink?" "Perfect." she replied.

Samantha plopped on the couch while I went in the kitchen to make her drink and refresh mine. I set her drink in front of her and sat down in my chair. I said, "I texted Joe earlier, he's going to call me tomorrow."

Samantha licked her lips, and said, "I hope that conversation goes well. I get wet every time I think about watching you suck a cock!"

I laughed and said, "I'm sure it will be fine."

Samantha said, "I texted my mom, she's good with the Mantua Inn. I told her 7. It's just going to be her." I nodded in agreement.

The Weekend Update segment came on on Saturday Night Live, which we quietly sat and watched, we both enjoyed it. When it finished, Samantha downed the rest of her drink, looked at me and grinned. She said, "Want to go to bed and see if you can make me cum?"

We headed upstairs, got naked and in bed. Samantha stretched and made a groan. "My back is a little sore. Can you rub me down?"

I replied, "It would be my pleasure!"

She rolled over onto her stomach. I straddled her at the top of her thighs, my semi-erect cock cradled in the crack of her ass. I leaned over and began massaging her shoulders and neck. She moaned quietly as my hands dug into her muscles.

After a few minutes I shimmied down and leaned into her back muscles, which were very tight. Her moans increased in volume, and I could feel her loosen up. I asked, "how does it feel?"

She murmured, "wonderful!"

After several minutes of massaging her lower back, my hands moved down and began to rigorously massage her cheeks.

She moaned and said, "I didn't say anything about my ass being sore." with a laugh

"Want me to stop?"

"No!" she replied with another moan.

After a minute or so, I slid my knee between her legs and spread them wide. I leaned in and began to run my tongue up and down the crack of her ass. Her moans got louder. After a few seconds, I spread her cheeks with my hand and stuck my tongue into her asshole. She gasped and her hand pounded the mattress.

"OH FUUUCK YES!" she gasped loudly.

After a couple of minutes, I reached over to the nightstand and grabbed the lube and the same vibrator she used when she gave an impromptu blow job in the living room.

She moaned as I slid a lubed finger into her ass. After I lubed her for a few seconds, I slid the vibrator into her. Once it was all the way in, I turned it on as she moaned loudly.

I rolled her over, leaned in for a quick kiss, then lowered my mouth to her pussy. She was already very wet. I licked slowly at the outside of her lips all the way to her clit.

I spread her lips and pushed my tongue into her pussy as far as I could. She moaned loudly.

After a minute of that, I slid my tongue to her clit and slipped two fingers into her and began to lick and suck on her clit. My other hand reached below and began to slightly move the vibrator in and out of her. She grabbed my head and pushed her pussy into my mouth. She screamed, "EAT ME!" Within a couple of minutes, she was bucking hard into my face. I gently bit her clit and she screamed. Her thighs locked my head and were trembling as she began to squirt.

I managed to press her thighs apart and pushed down to suck as much of her as I could. She squirted for nearly a minute. She reached down to pull my head away. I got up and straddled her on my knees with my throbbing cock nestled between her tits.

Samantha was still breathing heavily. She said, "I've never been eaten out before with a toy in my ass. That was fucking incredible!"

I leaned down to kiss her. She licked my lips and all around my mouth. "Mmmmm, I do taste delicious!" She slid her tongue into my mouth, and we kissed passionately for a minute.

I broke our kiss, grabbed the bottle of lube and held it between her tits. It dribbled in between her tits and over my cock. She smiled and reached up and pressed her tits against my cock. I leaned forward, supporting myself on the headboard, and started sliding my cock in between them. It not only felt good, but as I looked down, it was a very hot image sliding up and down, just out of range of her lips.

She moaned and said, "cum all over my face, the way I just did to you!"

Looking at her beautiful face, and watching my cock slide between her equally beautiful tits meant I didn't last long. I released a loud moan and said, "I'm cumming!"

Samantha closed her eyes as my cock shot its load, all over her face and neck.

Once I relaxed, I laid down next to her, nuzzling into her neck to lick myself off of her. I moved my head up, licking her cheeks and lips. I pressed my tongue into her mouth, sharing my cum with her in our kiss.

"Mmmm, you taste delicious too!" Samantha exclaimed.

She laughed and said, "it took you a month to titty fuck me! Every other guy I've been with usually wants to do that on our second or third date."

I laughed too, and said, "Well, you have amazing tits. I needed to earn that privilege!"

She grinned and said, "you earned that privilege during our second date!"

I started to get out of bed to grab a washcloth. She pulled me back and snuggled into me. "No, I want to sleep next to each other with our cum all over ourselves!"

We kissed and were both asleep in minutes.