Jokingly flirting with my former student led to fucking in front of my boyfriend [MF]

I’ve told a few stories about my open relationship with my boyfriend on my profile. This story is when our open relationship has been going on for a while. At this time, we’ve explored it together and individually and really started to be more confident in what we were doing. We knew what we liked and we really began enjoying it fully!

Now Harry had really emphasized his love for hearing about me fucking around. He’d talk about the thrill and the jealousy he’d feel and especially when I’d fuck somebody with a huge cock or a gorgeous body, he’d make me tell every detail. It became a huge turn on for me and I inevitably began looking for guys who would really get the biggest reaction out of him.

At this point I was in grad school and I was invited to a fun post semester party. The department was small and a lot of us had done our undergrad in the same department so it wasn’t unusual to have both undergrads and grad students at the same party. I also was a Teaching Assistant in the department so I spent a lot of time watching exams, teaching tutorials and having office hours. It was fun and it paid well (if you weren’t overworked) but it also gave this very taboo feeling when I had an attractive student. One of those student’s names was Dylan. He was tall, confident and I had seen him enough in my tutorials and office hours to know he was smart enough to get me excited. I also could tell that he had some attraction to me given the lingering eyes we’d give each other. He was 5 years younger than me which weirdly gave another thrill and appeal to him.

I opted to not overdo it that night and wore a white tube top and casual blue jeans with a nice red glossy lipstick. I had my hair up in a pony tail and was ready to just have a nice simple night with a few drinks and just a relaxing environment. When my boyfriend and I arrived, we were immediately greeted by loud bass and a living room dense with people I just didn’t recognize. It turned out the party was combined with another department and ultimately a lot of my friends were hidden in the back. Which made it much better when I finally saw Dylan as he was the only person I recognized.

“Hey Trish!” He’d yell, holding a beer in his hand as he approached with a beaming smile. “I really need to thank you. Without you, I absolutely would have failed this” he said before greeting my boyfriend with a handshake and an introduction on how we know each other.

“Please Dylan. I’ve talked to you plenty to know you could handle yourself!” I smiled back as I stared at his rolled up sleeves and strong forearms. I could feel a stronger attraction but played it off as I held my boyfriends arm.

​

The three of us ended up talking more and more as the crowd surrounding us almost moved in waves. One drink became three and I could immediately feel the buzz. I noticed Dylan’s jokes became funnier and our conversation drift from school to the summer to our personal lives. I don’t know if it was my attraction to him and our confidence in the lifestyle but we quickly opened up about the nature of our relationship.

“So Harry, you just like watching her talk to guys?”

Harry nodded shyly. “Yeah, I don’t know what to say. I like it”

“So if I just put my arm around your waist” Dylan said to me. I nodded back which invited him to hold me close to him. “This is something that you like?”

“I don’t fully understand either” I said back almost sarcastically. Dylan picked up on my tone and we continued the banter. We’d laugh at each other’s jokes, we’d give each other a hug. At one point we held each other’s hands as I gave Dylan a kiss on the cheek. Harry was laughing and playing along.

“Alright guys, this is the least believable thing I’ve seen. I can’t even help but be embarrassed” he joked as he left to get a drink. Dylan and I separated slightly as we talked more in the corner. We angled ourselves as we continued to talk about the nature of our relationship, Harry talking to another group in the corner of our eye.

“He’s watching us again” Dylan whispered into my ear as the crowd and music started getting louder.

I whispered back “Don’t worry. If he has a problem, he’ll come and tell me. We are open like that”.

“He’s really lucky. You are funny, open and the hottest TA I’ve ever had”. We continued to alternate talking into each other’s ears, each of us sending quick glances to Harry who continued his conversations while his eyes remained glued at us.

I immediately felt the butterflies in my stomach. I knew where the conversation was going and I could feel the tension starting to grow between us. I never fully embraced the fantasy and taboo of sleeping with a former student but at that moment it all came rushing to me.

I leaned towards his ear again. “No Dylan, thank you. You were a great student and you definitely put in the work. A lot of people just show up but you asked questions! I loved that”

“You made it easy Trish. I enjoyed it and you knew what you were talking about so it made it more enjoyable” he said.

I leaned forward again to respond only to realize his face was turned right towards mine and our eyes met, lips close but still far apart. Harry showed up almost perfectly, interrupting the inevitable.

“Alright, you guys don’t have to kiss. I get it now. What I like is weird” He laughed, thinking we were still bantering and joking. I gave Dylan a look and we both knew what we wanted.

“Oh no, we can kiss. We need to prove our point” I said before turning and pulling Dylan’s lips in for a quick peck. His eyes were in shock as his hands landed on my waist before we looked into each other’s eyes again before our lips met once more, this time lingering longer. I knew we were in trouble at that point but the music built up and the dancing began taking over the room.

“Let’s dance, give him the fantasy he wants” I said, pulling Dylan’s hand to the dance floor where our bodies were glued to each other as we felt other bodies bump into us. Harry stood in front of me, moving side to side as my hips and ass immediately met with Dylan’s crotch, gliding and moving to the beat. I could feel him getting harder as his hands moved from my hips to my stomach, his fingers hot to the touch as they slid under my shirt and back to my ass. The music continued to pick up as we moved from gliding to almost jumping as our hands were up and we separated, us three in a small triangle before Dylan and my eyes met again.

“Let’s go” I yelled. “It’s so crowded here!”. They both got the message and we walked through the crowd and out the front door. Harry continued to give us a stare of disapproval as we talked again. At this point, I quickly lost interest in the party especially as I saw more and more people I recognized. Harry saw this and opted to go home for drinks to end the night so he called the uber.

“Let me guess, you both now want to go back to our place for drinks and to play around more?” Harry continued, trying to pester us.

“Obviously. Do you think we are done messing with you” He said and smiled at me. At that point, I wasn’t sure if he was being serious but both just continued talking with almost zero discussion. The uber enventually arrived and we sat in the back, me in the middle with Dylan on my right and Harry on my left. Both left their hands on my lap as I rested my head on Dylan’s shoulder. The alcohol really started to hit at this point and he pulled up my chin and kissed me. I kissed him back as we quietly made out, doing our best not to get the attention of the uber driver. I could feel Harry hold my hand as he watched us kiss.

By the time we got back to our apartment, all of the pretences were dropped. Harry watched as Dylan and I continued to kiss and strip down, me pulling him by his hand and guiding him to the bedroom. I pushed him down onto the bed as my thirst started reaching unimaginable levels as I pulled his cock out and devoured it with my mouth. His moans drove me crazy as he continued to talk to me. His hips pushing up into me every time my tongue teased the head of his cock before he inevitably pulled his cock away and took control.

“You don’t realize how badly I’ve wanted this” he moaned as he threw me on my back and talked dirty in my ear. His cock stood tall and I started grabbing it and almost forcing it inside me. I gasped as he entered me. “Your ass in your tights and in your jeans, I’ve fantasized about fucking you in class” he said as he picked up his pace. My hands holding tight, my legs wrapped around him as I continued to beg “Please don’t stop!”. Our breathing continued to pick up as I saw Harry in the corner of my eye stroking himself as he watched.

The dynamic was incredible as I fought to take control, at one point positioning myself on top of him and grabbing his hands and putting it on my waist as I grinded my clit into him and rode him hard. Our tongues would meet and my hands would pull his wrists above his head as I moaned. “Let me fuck you right Dylan” I said as I saw his eyes shoot straight up and his head pull back in pleasure, the bed distinctly rocking back and forth by our motions.

“No, let ME fuck you right” he said before picking me and rotating me around, somehow ending up with me on all fours staring right at my boyfriend while he entered behind me.

“Fuck Trish, tell your boyfriend you love this. Make him cum” he said as one hand grabbed my ass and the other held my hair up, forcing me to stare forward. “I love this so much. His cock feels so good’ I continued to moan as Dylan’s pace and my boyfriend’s pace begun picking up until they both came almost simultaneously. We collapsed on the bed, complete messes, looking nothing like we did at the start of the night as Harry brought us glasses of water and kissed me hard. He told me he loved me and said I looked stupidly hot when I was as he described “thirsty as fuck”.

We talked more and the conversation almost immediately became dirty again. I saw he was quickly turned on again as we talked about my previous experiences and some of his fetishes. Dylan mentioned he loved my tights and lipstick so after we calmed down, I dressed up for him again this time in leather tights and another deep red lipstick and he fucked me one more time on my desk before leaving that night. I was sore and exhausted and Harry told me he loved watching every second of it. He continued to bring up that night (amongst others) as one of my favorites given it was one of the first times he watched but was not involved in the fucking.

Dylan wasn’t the biggest cock I had. I’d argue he was average in size but he loved playing the dynamic and the taboo of it all and it drove me crazy as we met each other a few more times that summer. Even though he wasn’t my student again, we role played and even fucked in the same office he’d come by for office hours. We explored some fetishes including BDSM and different roleplay dynamics (he loved fucking his “teacher” or somebody older) until he got a really nice girlfriend and our relationship stopped.

Thank you for reading and I hope you enjoyed it! Would love to hear what your favorite parts were as I prepare to write about another story in my past life. Dylan, if you read this, feel free to reach out and let me know if this is how you remembered that first night or if I’m misremembering anything.

Source: reddit.com/r/gonewildstories/comments/z5kfg0/jokingly_flirting_with_my_former_student_led_to