A Story for Women Around 40 or 50

Ladies, I need your thoughts

At 52 years old, I recently had my first sexual experience with another woman. I work for a travel agency and I travel a lot. My husband passed away almost 2 years ago and the travel has made it a little easier for me. I'm always busy either booking travel for my customers or traveling myself, so I don't have much time to think about being alone. Last month I traveled to Aruba and had to meet up with another agent from a different agency. We were to meet at the hotel and then room together.

I normally wouldn't do something like that, but I have been talking to this woman for a few years now and I feel like I know her, even though we've never actually met. Her name is Carla, and we were both pretty excited to finally meet and rate this hotel together. I got to the hotel around 2 pm and text Carla to let her know I was there. She was running a little behind and said she would meet me in the bar at 2:30, so I went to the bar and ordered my first glass of wine. At 2:30 on the dot, Carla came in.

We hugged and gave each other a quick cheek kiss. Carla was beautiful; if she wasn't so short she could easily have been a model with long sandy-colored hair, a beautiful face and a body to die for. Carla said, "Oh my God Janet, you're so pretty." With a little humility, I will say that I'm a decent-looking woman with an average body. I'm also 6ft. tall, so I do usually tower over most other women. I thanked her for the compliment and told her how good-looking she was as well. We sat down and Carla ordered a glass of wine. I was almost ready for another, but I wanted to let her catch up.

We chatted about our jobs, the hotel observations so far, and what we were going to do in our spare time there. We knew a lot about each other's personal lives simply because we talked so much; we just never actually met. After we both had 2 glasses of wine, we got our key and headed up to our room. We found out at check-in that our company reserved us a king suite and neither of us minded that.

As we opened the door, we both said, "Holy shit!" In unison. We laughed and walked in. Right in the center of the room was a hot tub surrounded by a half-circular sofa.

I looked at Carla and said, "I know what I'll be doing when we're in this room."

Carla said, "Oh yeah, but we need a lot of wine to go with this hot tub." We laughed and decided to go have an early dinner then maybe go to the pool since it was open at night and so was the swim-up bar. Dinner was amazing and we went back to the room to change into our suits. The first thing that tipped me off that something was up, was when we got back to the room and Carla started stripping right in the living room. We were both feeling pretty good, but I thought that was a little weird.

I chuckled and said, "Wow girl, have you no shame?"

Carla said, "I assume you have two tits and a pussy just like me, so nope, no shame at all." I laughed and then she said, "What, are you ashamed of your body, are you shy little girl? Do you want me to leave so I don't see your little chochie? I laughed and not wanting to feel like a prude I unbuttoned my shirt and took it off. Carla said, "Wow, nice tits there girly, much nicer than mine."

I was actually feeling more comfortable so I said, "Nah, yours are damn nice too, just a little smaller." I went to my room and put on my bathing suit. It was a one-piece, but the piece that connected the top and bottom was minimal, and it just gave it a very sexy look. The ass was very high-cut, so my legs looked like they were a mile long.

I walked out to hear, "Shit mama, you look sexy as hell in that."

I replied with "Me? Look at that hot ass body wearing almost nothing." She was wearing a thong with a tiny top that barely covered her small tits. That was the very moment that I got my first tingle in my girly parts looking at her. She was both beautiful and sexy. We went down to the pool and we were surprised to see only a couple of people there. We walked into the pool that was the perfect temperature and we swam over to the bar. We each ordered the "special" drink of the day, and boy was it strong.

We swam to the opposite end of the pool and sipped our drinks as we chatted about different things. Carla was 3 years younger than me and she was divorced with no children. At one point she called us the "two lonely spinsters" We both laughed and started talking about how lonely we really were. At one point as our talk got a little deeper, Carla reached up and tucked a piece of hair behind my ear. It was an innocent gesture, but something about it sort of turned me on.

As we talked and drank, I realized our eyes were locked on each others and the looks were getting a little more serious. After a few minutes and a brief lull in the conversation, Carla leaned in close and put her lips about an inch from mine. I want to blame it on the alcohol, but it was totally my decision to lean in and kiss her. I'm not sure if it was the mystery of kissing another woman, or just the loneliness since losing my husband. Either way, I was really enjoying it. We kissed for a long time in the back of the pool, basically by ourselves.

When we broke it off I said, "I'm not exactly sure why I just did that, and I'm sorry if that upset you."

Carla said, "Do I look like I didn't fucking enjoy that?" She smiled and said, "If you didn't kiss me, I was going to kiss you, so no I'm not upset at all; in fact, I hope there's more." I didn't know if she meant more things to come, or if she meant more kissing. Either way, I was drunk enough, and lonely enough to go for anything. She tucked another hair behind my ear then kissed me again. My pussy started to get wet and it wasn't from the pool.

After we broke the kiss Carla asked, "Should we go upstairs before we do something we're not ready for?" She had a really cute smile on her face and it was really getting to me.

I said, "Yeah, that's probably a good idea, and I just want to tell you that's the first time I've ever kissed another woman, and I'm glad it was you."

Carla said, "I feel the same way, and I really liked it too." We made our way to the stairs and headed up to the room. We both took showers and decided that, after all those drinks it was time for us to go to bed; after all, we did have some work to do tomorrow. We each went to our rooms and as soon as I closed the door, I stripped off my sweats and climbed into bed naked. I instantly started to masturbate and was really upset I hadn't packed my vibrator. It didn't take long before I gave myself an orgasm thinking of the hot kiss I had with Carla in the pool. I fell asleep thinking of what Carla would look like naked.

The next morning those thoughts from last night were confusing the hell out of me, I'm a heterosexual woman; I'm not bisexual, or am I? My head was pounding and after brushing my teeth, I found some aspirin and immediately took two. After getting dressed I went into the living room and saw Carla making coffee. She looked at me and said, "Coffee?" I nodded yes and she laughed. "Looks like somebody had a rough night."

I said, "How the fuck do you look so good after all that drinking last night?"

"Make-up, lots and lots of make-up."

I chuckled and said, "No, that's a natural beauty you have, and before we go any farther, I want to apologize for what happened last night, I was pretty drunk."

Carla walked over to me, stood right in front of me, and said, "I told you last night, I enjoyed that kiss and if you didn't do it, I was, so shut the fuck up and drink your coffee." Then she leaned in and kissed me again. This time it was a simpler kiss, just lips to lips, but she held it for a couple of seconds before she broke it off. Then added, "We have a meeting in 20 minutes." I walked over to get my coffee and immediately felt some new dampness between my legs. We went to our meeting with the hotel manager and did our tours.

The day ended pretty early around 3:30 and we decided to go shopping at a nearby tourist area. We did some shopping, a little drinking, and some sightseeing. At around 6 p. m., we decided to have another drink and then find a nice place for dinner. Our first stop was señor frogs, a very touristy place bar and we wound up having two drinks before we left. I said, "That was a fun place, but a little too touristy for me." Carla agreed and we decided to find a nice quiet place for dinner. We found this very cute restaurant called "The Old Man and the Sea." It was a very quiet, and dimly lit area right on the beach. Our toes were in the sand as we ate dinner and I suddenly realized, it was a very romantic setting. It was accidental, but it actually fit the moment.

We talked some more, and this time Carla was getting pretty deep about her emotions, her life, and her loneliness. In turn, I did the same thing, but for me that's not normal. I am generally a closed book not showing my emotions, but with Carla, I felt very comfortable. I let her know that, and she told me she felt the same way with me. Once again by the time we finished dinner, we were feeling pretty good. We decided it was time to head back so we called a cab and waited in the lobby. As we walked to the lobby, Carla took my hand and for some reason, I really liked how it felt holding her hand. The cab came in 10 minutes and we had about a 15-minute ride back to our hotel.

We sat together in the back and out of nowhere, Carla leaned in and kissed me again. This time it felt a little strange because I was kissing another woman in this cab with a male driver in the front. Carla must have noticed I was a little different this time and she stopped kissing me, then she whispered, "Relax, it will give him something to jerk off about later, now kiss me bitch." I smiled and kissed her more comfortably this time. We arrived at the hotel, paid the driver, and headed up to our room. As we were walking, or more like staggering, to the room Carla said, "That kiss made me really wet." I gave a nervous laugh and she added, "TMI, I know, but that's just how you make me feel."

I stopped walking and she turned to look at me. I said, "Hmmm, I guess that's why I feel like I'm wearing a wet diaper too." We both laughed harder than normal because we were pretty drunk, but it was honestly the best laugh I've had since my husband passed, and I told her that.

Carla's response was perfect; she said, "Well Woody Allen has a famous quote: (Sex is the most fun you can have without laughing.)" Then she walked down the hall towards our room. At that point, I knew tonight was going to be something I'd never experienced before. We walked into the room, closed the door, and I was stopped dead in my tracks by Carla standing right in front of me.

I somewhat drunkenly said, "Can I help you?"

"Yes you can, you can help me fill up that giant shower that's in my room; it's so big sometimes I get lost in there." Then she leaned in and gave me a very passionate kiss that lasted for about a minute.

We broke off and I said, "Does that mean we're both going to be naked in there?"

"It does."

"Then show me the way." I couldn't believe what was about to happen; I'm a totally straight woman, or at least until now. Carla took my hand and we went into her room. Before we even got into the bathroom, she started to get undressed. I joined her and within a minute we were both standing there naked looking at each other. I said, "Fuck, you are even more beautiful naked."

She responded with, "Back at ya, but I need to see more; give me a look at that tiny little ass." I slowly turned around and gave her a full look at me. When I was facing her again she asked, "I just want to make sure we're both ok with this, it's something new for both of us, but there's just something about you that turns me on like no one ever has."

I said, "Shut up bitch, and turn on the shower. We walked into the bathroom and Carla turned on the water to warm it up. I walked in and Carla followed, putting herself in front of me. She immediately put her face and hair under the water and when it was wet, her auburn hair went halfway down her back. I opened a bar of soap, put it in the palm of my hand, and started to soap up her back. Showering with another woman was a whole new experience for me. My husband and I took showers together all the time, but this had a whole new meaning; I couldn't get enough of her body. I completely soaped up her back and slowly made my way to her ass. As soon as my hands touched her she let out a small, "Mmmm."

I leaned into her and whispered, "Should I keep cleaning you?"

She said, "That's why I brought you in here with me." Then she slightly pushed her ass into me. I went between her cheeks and as soon as I did, she spread her legs apart giving me full access. I started with her ass and slowly went further down until I felt her lips. They were tight but thick, just like mine get when I'm really horny. I stayed on her pussy for a few minutes then went back up her ass and then her back. She turned around and said, "Mmmm that was nice, but now I need my front cleaned, are you up for the job?" I just smiled and put both my hands on her tits. Carla's tits were a little bigger than mine, but they seemed to fit perfectly in my hands. I played with her nipples a little then made my way down her flat little stomach. Her abs were amazing and I just stayed on her stomach for a long time feeling how muscular they were.

I looked up at her and her eyes were closed, so I leaned in and gave her a nice kiss. When we finished she opened her eyes and said, "There's still a part that needs some cleaning."

I answered, "I know, I just can't get enough of your body; I just want to feel every inch of it." Then as I looked her in the eye, I let my hand go down and I started to soap up her pussy.

As I played with her she said, "I can't believe I'm letting you play with my pussy."

I responded with, "I can stop if you want me to."

"Don't you fucking dare." She said. I smiled and as I continued to play, I found her clit and her knees buckled. I wanted the night to last forever so I only played a few minutes then handed her the soap and told her it was my turn to be clean. Unlike me, she didn't start slow; she soaped up her hands and reached right for my pussy. She smiled at me and said, "Sorry, but I couldn't wait another second; I needed to feel your pussy." Then she added, "Mmm, it feels a lot like mine."

I said, "Good, then you know exactly what to do to make it feel good." She smiled and nodded her head. She stopped playing and cleaned the rest of me, taking a little extra time on my ass. We got out, dried off together, and headed to the bedroom.

I was so horny that even though I just dried myself off, I could feel my pussy was already getting wet again. I climbed on the bed and Carla just stood there looking at me. I asked her if she was joining me and she said, "Of course, I just wanted to see you lying there naked on my bed. I smiled, raised my knees, and opened my legs.

"How do I look?" I asked. Her eyes were glued to my pussy and she didn't say a word. I suddenly felt a little awkward lying there spread-eagled while this woman was staring directly at my pussy. I asked, "Is everything ok? Are you having second thoughts? We can stop right now if you want."

She leaned over and just before planting a kiss on me she said, "Everything is fine; I'm just trying to figure out the best way to eat that pussy." Then she kissed my lips and went down my body one kiss at a time until she was right above my pussy. She rearranged herself so she was lying in front of me on her stomach and the next thing I knew, there was a tongue licking my pussy lips. I held her head as she expertly ate me out. As much as I always enjoyed my husband doing this, there was no comparison; this girl knew what she was doing. I could hear myself moaning, but I couldn't stop; it felt so fucking good.

I managed to say, "Oh shit you're good at this." As my hips went into overdrive. She just continued to lick my pussy from my ass to my clit and everywhere in between. After a few minutes, I felt myself getting ready for an orgasm, but when I told her, all she did was lick me faster and harder until I started cuming. I had to pull her away because I was getting too sensitive. She climbed up next to me and asked how she did. I said, "That was fucking amazing, are you sure you never ate pussy before?"

She chuckled and said, "No, but I promise you, that won't be the last time. I just couldn't get enough of you." Then she surprised me by saying, "Here, taste how good you are." Then she leaned in and gave me a deep tongue kiss. Her face was wet and that just turned my sexual appetite up even further. We broke the kiss and she lay flat on the bed. The next thing I knew she was playing with herself. I watched as she ran her finger between her lips, rubbed her clit then slipped her middle finger in for a minute. She took it out and made a wet trail up her stomach then pushed her finger into my mouth.

It was the first time I've ever tasted a woman's pussy and it was amazing. She said, "I just wanted you to sample the menu before you had your meal."

I smiled and said, "I'm not sure I got a good enough taste; can I try that again?" She reached down, spread her legs wider, and stuck two fingers into herself. This time she was going at it a little harder so as I watched this beautiful woman finger herself I said, "Make yourself cum, I want that pussy super wet." She picked up the pace and feverishly started fingering herself as she stared at me

A few seconds later she grunted, "I'm cuming, this is for you." I could actually hear how wet she was getting and the more she fingered, the louder it was getting. Suddenly I heard, "Uhhhhhh." as she came really hard. She pulled out her fingers, but this time I grabbed her hand and put those two fingers in my mouth; they were very wet. As she lay there catching her breath, I just looked down at this beautiful woman recovering from a massive orgasm. She smiled and said, "Did you enjoy that?" I didn't say anything; I just smiled and nodded my head. Then to my surprise, she raised her knees, opened her legs, and said, "My turn."

I couldn't believe she wanted to have her pussy eaten after a big orgasm, so I said, "Wow, no recovery time, huh? You want to get right down to business don't you."

"I think I've waited long enough because now I really don't want you anymore; I realized I fucking need you." Then added, "Now let me feel that tongue of yours." I repositioned myself and now I was face down looking directly at her pussy. Hers was a little tighter-looking than mine; her very pink lips made it look amazing. Her clit looked a little bigger than mine as well, so I knew that would be a good place to start. I used my tongue to twirl around it and then up and down her lips. She was moaning pretty well, so I knew I was doing a good job. Her hips, like mine, were in constant motion as I licked and sucked her pussy into I felt her tighten up; I knew she was on the verge of another orgasm.

I used my two thumbs to spread her lips apart so I could get my tongue in as far as I could. As I did that she said, "Oh fuck, what are you doing to me? Fuck, I'm gonna cum again." Seconds later I was licking this wild bucking bronco as she came hard. She pulled me away and sat there breathing heavily. When she calmed down and was staring at the ceiling she said, "Fucking liar!"

I was a little taken aback and said, "What?"

She responded, "You're a fucking liar; there's no way that was your first time eating pussy." Then she sat up on her elbows and said, "My pussy has never been eaten that good, so I know you're a liar."

I knew she was kidding so I said, "You're right, I eat pussy all the time, but yours is amazing."

She laughed and said, "You know just what to say to make a girl feel good, don't you?"

"Well, I lied about eating pussy all the time, but I didn't lie when I said yours is amazing." We kissed again and I said, "Is this enough for tonight? We have a few more days yet and we can ease into it."

She laughed and said, "Fucking ease into it? You just gave me two of the best orgasms of my life; that's not easing into it, that's going for the gold." We both laughed and I turned to have my back facing her. We fell asleep spooning. The next morning I woke up and Carla was still hugging me from behind. I looked at the clock and almost had a heart attack. It was 8:45 and we had a 9:30 meeting. I woke up Carla and we both jumped into the shower together.

Carla said, "You're lucky we're late or I'd be all over you right now."

I said, "Oh, just because you took advantage of me last night when I was drunk doesn't mean you can have me whenever you want."

She laughed and said, "Oh yeah? I think you took advantage of me." We both laughed, got out of the shower, and frantically got ready for our meeting. Our workday ended early again and we decided to go hang at the pool until it was time for dinner. We were getting ready for the pool, and as I came out of the bedroom wearing my bikini, I saw Carla getting her bag ready to take down with us. Now as much as we did the night before, for some reason Carla looked even sexier wearing a bikini than she did naked, just hot as hell.

She walked over to me and said, "Look at you, you sexy bitch." She leaned in and kissed me. As she did, her hand slipped inside my bikini and she started to tease my pussy. I broke the kiss and said, "What are you doing? I can't go to the pool with a big wet spot on my bottoms."

She smiled and said, "Don't worry, if they get too wet I'll help you take them off." I gave her a quick kiss and she took her hand out of my pants. We went down to the pool and ordered a couple of drinks. After drink number two Carla said, "Let's play who would you fuck, but girl style." I laughed and she said, "Ok, I'll go first. See the girl in the blue thong, I'd fuck her."

I laughed and said, "Nahhh, she looks like a prude, I need somebody freaky, like her, the one in the red one-piece suit over there." Carla agreed and then picked out a couple more. I asked, "Do you have any regrets about what we're doing here? I mean it's a first for both of us, and it seems like we both went into this a little too easily."

Carla said, "I know what you mean, I was thinking the same thing, but if it feels right, there's nothing to think about, so no I have zero regrets. None!" I told her that made me feel so much better that she was thinking the same thing as me. Then Carla said, "Ok, so back to picking out a girl for our first threesome." We both laughed and went back to playing our game. Around 5:30mwe decided it was time for dinner, so we went upstairs, got dressed, and headed out for a nice meal.

We got back to the room around 10 pm and once again, I was horny as fuck. When we closed the door, I walked over to the sliding door and went onto the patio. The patio had a solid wall surrounding it that was about 4 feet tall. We were on the 21st floor, so the view was incredible. I was standing there leaning against the wall looking out over the ocean when I felt Carla come up behind me. She hugged me, rested her chin on my shoulder, and said, "This trip is fucking amazing. I couldn't have wanted you more when I first saw you, and now we've shared ourselves." I turned to the side and kissed her head. The next thing I knew, as I was leaning on the wall, Carla's hand went up my skirt and inside my panties.

I said, "Oh you nasty little girl, we can't be doing this out here on the balcony."

She responded, "Wanna bet." Then she used her other hand and pulled my panties down and then off. Her hand went back up and as I was staring out at the ocean, my new girlfriend was playing with my ass.

I let out a small, "Mmmm, that feels good." And she just kept rubbing my ass with an occasional dip a little lower to brush against my lips. I said, "Are you going to take advantage of me again, I'm not that drunk tonight; I might just say no."

As she reached under and parted my lips she said, "I plan on taking complete fucking advantage of you tonight; I might even have to use my dildo on you." I didn't know she brought one with her, but I was ready to try anything.

I said, "Good, I need to be taken advantage of." Then I turned to face her. As I did, Carla pushed two fingers into me. I was half-squatting with my back against the wall. I said, "Why do I need you so bad?"

Carla said, "We both need each other; now shut up and let me finger your pussy to an orgasm." I relaxed myself and a minute later I was dripping all over the balcony having a massive orgasm.

As I was cuming Carla said, "Maybe somebody is watching us right now; maybe they're watching you cum, do you care?" I shook my head and just let her do whatever she wanted to do to me. I finally finished, stood up straight, and kissed her again. When we broke the kiss Carla said, "I'm gonna go get my dildo and I want to be fucked with it out here on the balcony, do you think you can do that for me?" I assured her I would and she went inside. She came back a couple minutes later naked, and carrying a dildo and two glasses of wine.

I said, "Well somebody's ready for some action." She smiled, handed me my wine, and leaned over the balcony wall. In reality, she's short, so no one could really see anything from below, but looking at her naked against the black night sky was very sexual. I reached for the dildo, licked it a few times, and traced it down her back and in between her cheeks. As I did that, she pushed back a little and spread her legs apart. She was in the perfect position to be fucked, and since I was the only one with a cock, it was my duty to take care of this woman. I quickly realized I didn't need to lick it; this woman was soaking wet and was ready to be fucked.

I slowly pushed it against her pussy until I felt it start to sink in. As it got deeper, she let out a soft moan. I said, "How's that feel?"

She said, "It feels like I need more." Then she pushed her ass back a little further forcing it to go further inside her. Again she let out a moan and I started to slowly fuck her with it.

As I fucked her I said, "How does it feel looking out at the world while you're getting fuck?" She just moaned a little more and let me continue to fuck her. After a few minutes, I abruptly pulled it out and pushed two fingers inside her; I needed to finger her to an orgasm, just like she did to me. It didn't take long before she was cuming like a waterfall all over my hand. This girl was a squirter. She almost collapsed as she orgasmed and I really think the only thing holding her up was my fingers inside her. She finally stood up making my fingers slip out.

She turned around and said, "I can't believe how you make me feel; I just want to fuck you all night."

I smiled, kissed her, and said, "Well I got nowhere to be." I took her hand and we went into the bedroom.