Sex with Teacher in Cuba

When I was a senior in high school, a trip to Cuba was arranged for everyone in AP History – about 60 students in all. I didn’t overly care about Cuba, but I appreciated the chance to get away to a hot climate and to have a break from school and my family. Most importantly, my favorite teacher — the one I had a crush on, lusted after, and frequently masturbated to, Ms. Gordon — was going to be there. We actually had a great rapport in class, and I looked forward to the prospect of bantering with her as we toured and dined in a hot foreign country where, I hoped, she might wear some clothes that showed off her large breasts.

Deep down, as much as I joked with my friends about how hot she was, this was just a fantasy. I had a loving girlfriend, Rebecca, that I was committed to. Besides, I was only 18 – I wouldn’t know what to do with a grown woman if I had her. Ms. Gordon I knew had just turned 40, and had dark hair, very full breasts, and a slightly curvy figure without being at all fat. She was authoritative, but if she liked you and you didn’t give her problems you’d find out that she was really cool and had a sharp sense of humor. History was my last class of the day, and I’d often hang around and chat with her about TV shows or whatever else. She was the first adult I ever met that I could relate to.

I said goodbye to my family for the week, and also to Rebecca. She made me promise not to hook up with any of the pretty girls who were also going on the trip. Rebecca and I had had sex a couple times, but we were both very awkward at it, and the condoms made the experience pretty lackluster, to be honest. Still, we were “in love” — she was my sweetheart, and she was planning on going on the pill as soon as we graduated in a couple months. No one from my closest circle of friends was going, but lots of people I got along fine with. And so we took the plane to Cuba.

As with most class groups, it was a rowdy bunch, with lots of moving about and trading seats. Halfway through the flight, the student sitting next to Ms. Gordon went to the bathroom, and I took his spot next to her. We established a jokey banter and she smiled and told me that I would have to be in charge of keeping her sane this trip.

Every day, our group would break into smaller groups, and then go on some instructive field trip. At night, we’d come back and go out to pre-designated restaurant for dinner, and then return to our hotel. Students were grouped in large rooms of five, with one parent supervisor, and teachers stayed in smaller rooms of two. The days were busy and fun, and I managed to hang out with Ms. Gordon a fair bit. We’d make sarcastic comments to one another when no one else was within earshot. If we were on the same daytrip, we’d sit at the same group table for lunch. I’m pretty sure she knew I had a thing for her. On the last few days of the trip, she started to dress more risque – sheer tops that showed a sports bra underneath, for example. Really hot.

For my part, I had gotten pretty much all I wanted. A nice vacation, and some attention from the sexy object of my masturbation fantasies. I imagined her mouth on my cock, me feeling her huge breasts, as I quietly stroked myself to ejaculation one night in the bathroom, spraying semen all over my hands, imagining it was into her welcoming mouth and probing tongue.

On the last night of the trip, the atmosphere loosened up considerably. The parent and teacher supervisors looked the other way when it came to the members of the graduating class, and so several of us and a couple of the “cool” teachers and parents ended up at a bar about fifteen minutes from the hotel. To my delight, Ms. Gordon was one of these teachers, and the night flew by as we drank beers and laughed with the group. Slowly, people began to head back. A small cluster of us stayed and continued to drink. I spent a lot of time just talking with Ms. Gordon – who asked me to call her by her first name, Susan – and the conversation strayed in all sorts of directions. She asked me about Rebecca, my plans for college, my passions. I asked her whether she was seeing anyone (no, it had been too long), why she broke up with the last guy (he didn’t want kids, she did…), why she decided to be a teacher (summers off…), what her advice was for me (travel…), and so on. We had a good connection, and there was definitely a chemistry at work. She made a couple comments that indicated to me that she knew how into her I was, and at one point mentioned something about how “sexual” a person she was, which even immature me knew was a definite green light. She said she was going to the washroom, and I said I had to go too, and when we rounded the corner, in my drunken haze I leaned in to kiss her. She responded passionately, but pushed me away, laughed, and said we’re going to be caught and that that would be really fucking bad. “Let me see what I can do” she said.

When I got back to the table she was already there, and everyone was packing up to leave. As we were walking, she took me aside. “Want to come up to my room to talk for a bit longer? Ms. Innes had a room all to herself, and I traded with her. I told I was feeling sick and didn’t want to share the room with Andrea tonight!” I said yes with my mouth before my mind totally caught up.

We trailed the remnants of the group back to the hotel. When we arrived, I said goodnight to Ms. Gordon with everyone else, and she whispered her room number into my ear. I took the elevator up and down a couple times before heading to her room. I almost got cold feet, but the alcohol kept me immersed in the fantasy. I didn’t want to hurt her feelings by not showing up. I decide we could just talk a little longer, and I would apologize for the kiss.

I knocked on the door, and Ms. Gordon answered in a shirt and shorts. She told me to come in and prepared me another drink while I sat on the bed. I started to feel weird. The impossible nature of the romance, that had freed me to pursue and indulge it with abandon, had disappeared. Suddenly, I was very much aware of the potential consequences. I was cheating on Rebecca. As well, something about the situation felt tawdry. I remember being very aware of the textures of the hotel room, how cramped and impersonal it was. You have to remember, for all my youthful bravado, I had only had a few fumbling sexual encounters. Sex was still foreign and romantic for me. I thought I would finish my drink and then say goodnight.

She gave me the drink, and told me that my being here was absolutely between us, and I agreed, telling her she could trust me. She said she knew I had a crush on her for a long time and thought I was cute.

She also told me she got Greg, one of the other seniors who was out with us, to stay in my room instead of me, with the same excuse that she had used for herself… that I was sick and needed quiet. Greg’s room was only half full and his absence wouldn’t be noticed. She told me I would spend the night with her. I realized I couldn’t easily go back to my room — there was another body in my bed, and I didn’t have the key to Greg’s room. I considered just wandering around until sunrise, but that was a long ways away. I thought maybe it wouldn’t be so bad to stay here, I could just exaggerate my drunkenness and pass out in bed.

She asked if I would take a shower before getting into bed and I agreed. It was actually nice to wash up without five other guys waiting in line. I finished, then put on my underwear and t-shirt, wrapped a towel around myself, and walked out. Fiona smiled and said that she was going to get ready for bed and take a shower too, and that I should just get in bed. Perfect, I thought, and tried to get right to sleep.

Several minutes later, she got out, and walked over to the bed, illuminated only by the bedside lamp. I peeked through squinted eyes. She was wrapped in a towel. As she got to her side of the bed, she dropped it and was completely naked! Her breasts were incredible, full and round, a few light blue veins running underneath the pale skin, with large hard brown nipples. Inbetween her lovely wide hips, a thick mess of black pubic hair covered her vagina.

“You’re not asleep already are you? I don’t think you’re going to want to miss this” she said playfully. When I didn’t respond, she shook me and I opened my eyes. She smiled and said “well?” And jiggled from side to side, her breasts staying to and fro. I was taken aback that she was quite so comfortable with her nudity. With my sweet little girlfriend, Rebecca, things had always been in the dark, under the covers. This woman in front of me was proudly showing off her large bare breasts and vagina.

She got into the bed and noticed I was still wearing a t-shirt. She smiled and said, “do you always wear a dirty t-shirt to bed?” before saying “here” and prompting me to sit up so she could pull it off me. She began kissing me, sliding her tongue into my mouth immediately, and running her hand along my chest. I tried to keep up, receiving her tongue and kiss back, since I didn’t know what else to do. She slid her hand down to my underwear, past the elastic waistband, and around my penis. I wasn’t hard. It was probably some combination of anxiety and the alcohol, and I figured this finally would be the limit of the encounter.

However, Susan didn’t seem put off. She tugged at the sides of my underwear, told me to “lift”, and then took them off my feet, so that I was completely nude like her. She said “I think you just need to be more comfortable. You’re safe with me. We have lots of time.”

We continued to make out for a while, and then she straddled me, and continued moving up my body, and I realized she was going to put her vagina on my face. What a dominant gesture – Rebecca would never have the confidence to do such a thing. I licked at the inside of her pussy and clit, doing the best I knew how, and she grinded on my face for a while. While she was doing this, she reached back and played with my cock and, before I knew it, I was fully hard. I guess seeing a woman so in control of her sexuality was a turn on.

She lifted her leg from the side of my head, moved down my body, and took a look at my penis. “You’re uncircumcised,” she said – I didn’t know if this pleased her or not. In any case, she took my erection into her mouth and began sucking it, using hard tongue pressure that felt incredible. At one point, she slid her tongue into my foreskin and dragged it around my glans, which felt unbelievably good.

She came up and kissed me, I could taste my cock on her breath. She told me, “I love a big penis on a smaller guy.” At 5’8″ I didn’t consider myself that small. Her statement – and lingering thoughts about Rebecca – distracted me long enough for her to kneel up, take my penis, position it at the entrance of her vagina, and sit down on it so I slid all the way inside of her in one thrust. I was fucking – being fucked by – Susan Gordon. She was soaking wet.

She was straddling me, riding me, and her huge breasts were in my face. I couldn’t help but lean up and take one of the large nipples into my mouth. “Good boy,” she cooed, “suck my breasts, that feels so good.”

I was aware that I was cheating on Rebecca, my girlfriend, my first sexual partner, my confidant. At the same time, Susan’s pussy felt so incredible on my penis. I’d never had sex without a condom, and it felt a whole world apart. My foreskin was being pushed back on her labia and vaginal entrance and my bare glans was being pushed all the way up inside of her. I resolved that I wouldn’t ejaculate inside of her. I had never done this with anyone and would save this special occurrence for Rebecca.

Susan was riding me hard, and I watched as my slick penis, rhythmically slid out of, and then was pushed back inside, her pussy. She leaned forward, and started to really move her ass up and down. She also started to kiss me while we fucked. “You’re doing so good, sweetie. Your cock feel really good.”

I felt myself getting close, and tried to push off. “I’m going to cum…”

“Cum inside me, sweetie. I want you to cum inside me. Shoot inside of me.

Cum inside my vagina.”

Hearing her say “vagina” really did it for me. Susan was clinical, mature.

I didn’t want to cum inside of her. For Rebecca and, also, I suddenly realized – was Ms. Gordon on the pill? We hadn’t discussed protection at all. I had no idea. She was 40, but I thought I remembered that women that age could still get pregnant.

I tried to push her off, to pull out, but she put all of her weight down on her hips, as she rode me very strong and close to the bed, smothering my mouth with her tongue, and I couldn’t help it – I shot an enormous load of my sperm inside of her tight vagina. I felt her nipples hard against my chest, as I felt spurt after spurt go off inside of her. Having bareback sex was intensely pleasurable, but being able to ejaculate inside of an unprotected vagina was equally if not more incredible. She held me tight all through my orgasm.

After several moments of being lost in bliss, I came out to see Susan’s big breasts still hanging down over me and her face smiling. “Feel good?”

“Yeah…” I muttered, although shame and regret was sinking in.

“Have you never come inside of a vagina before? How did you like it?”

“It was really good…”

She laughed, “yeah, I thought you would like that.”

Still straddling me, she reached for a hair tie on the bedside table, and drew it over her hair. She lifted off of me, and my limp penis fell out of her. She used one hand to prevent my sperm from dripping out of her vagina, and walked to the bathroom to pee and wash up.

I lay in bed and gathered my thoughts. Tears began to form in my eyes as I thought about Rebecca, and as the seediness of the situation set in. I’d only ever had romantic loving sex before, never a one night stand. I’d always been “the man”, I’d never been the one getting fucked. I was worried that we hadn’t use protection. The emotions were confusing.

When she got back, she turned off the lights, and we slept facing opposite directions with our asses touching.

Source: reddit.com/r/eroticliterature/comments/7jiejk/sex_with_teacher_in_cuba

1 comment

  1. Wow outstanding. I felt I really got inside the main characters head. Really well written; thankyou!

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