[F] Two Boyfriends Too Many

My first submission (this one is the second) I wrote about how I got together with Jeff, and this describes the other end of that relationship, with overlap. I guess these writings may turn into a sexual autobiography.

Jeff and I were together, or having sex frequently, I guess is a more accurate label, for about three years total, with starts and stops. We were within a year in age, both early twenties, and we genuinely enjoyed each other physically. We fucked like rabbits, every chance we got.

I was not that experienced, he could not have been either, so our routine now seems in retrospect, well, routine. He was a student at a local college, and still living with his parents; I got a job right out of high school and got out on my own as soon as I could, renting a room in a townhome owned by a divorced lady.

So, we went out on dates plenty, hung out at my place plenty, and then one way or another, we’d start fooling around either on the couch or in my bedroom, and then we’d fuck, and then he’d go home. Sometimes he would spend the night and then we’d fuck again in the morning.

It may sound boring, but he had a nice athletic build, he was wonderfully passionate, he had a beautiful hard cock, and he always made sure I orgasmed. We tried different things during foreplay, occasional oral but honestly, I wanted his cock in me; and when I sucked his dick — rarely, and I laugh about this now — I did not want him to cum in my mouth.

Maybe he was being nice, he said he liked fucking best anyway. So, that was our routine: one of us would start things by fondling the other, maybe he’d reach up under my shirt; we’d kiss, he would get hard and I would get wet, he would roll over on top of me, I would put my heels up in the air as he fucked me missionary for a while, tongue-kissing the whole time, then he would flip me over onto all fours and fuck me till my ears fell off from cumming. And then, usually after some perspiration, he’d fill me up with himself, usually when I was also in mid climax.

There was no uncertainty about when Jeff ejaculated, he announced it before and during, his whole body seemed to explode inside me, and he was very productive — occasionally he would pull out and he could squirt all the way up my back into my hair, if I was face up I turned my head to make sure I didn’t get a shot in the eye LOL.

But as good as the sex was, we did have our starts and stops, I don’t think either one of us expected or even thought about “forever,” we were just fucking and having fun, but we did get jealous occasionally or say the wrong thing, and we’d angrily part ways. Then after a couple of weeks or a month typically, one of us would call the other, just to say hi, and we’d be back at it.

During one longer than usual “interruption” I had jury duty, and I met Sherman. we sat next to each other for hours. He was very handsome, older than me, he was around thirty-four and I was twenty-two or twenty-three. He was charming and made me laugh, at the end of the day we exchanged information. We went out for a nice dinner that Friday night and when he dropped me off, for his goodnight kiss, he moved his face near mine and inhaled, his nose very near my ear, whispered that I smelled wonderful, and then kissed my earlobe very slightly. I liked it, so I welcomed another kiss, this this time very lightly on my lips, then he barely touched my lips with the tip of his tongue. It heated up quickly, plus I had not had sex in a couple of weeks … I invited him up and we fucked — for two hours. I was exhausted afterward, fell into a deep sleep and when I woke up, he had let himself out, left a sweet note saying he hoped he could call me again soon, and he did, later that day. We started seeing each other frequently.

Sex with Sherman was very different from my prior experience, and I remember now that at that time in my life, it surprised me, happily. It was not two hours every time, but it was certainly more of an event with Sherman, with more variety. For one thing, he loved cunnilingus, and most every session, he would first bring me to one or two orgasms with his mouth and tongue, before fucking me. He knew what he was doing, knew his way around my clitoris. He used his hands, fingers, and fingernails lightly all over me, he feather-kissed down my back, he loved wet-kissing my nipples and then blowing on them to make them hard.

He teased me with his thick cock, only putting it in a little until I begged him to fuck me. He enjoyed different positions. He would cover the bed with a vinyl sheet and cover us in baby oil so that we were slipping and sliding all over each other. We would fuck in the shower together. We would talk, sitting up face-to-face, about what each other liked sexually while his dick was inside me.

He encouraged me to be freely sexual. He took me to an adult store and bought me a little vibrator, and we would watch each other masturbate to orgasm. He gently suggested he would enjoy my wearing sexy clothing in public, with no bra, shorts skirts and blouses that showed my pokies in public. I do not mean he wanted me to dress like a hooker (no disrespect to professional sex workers), he simply encouraged me to have what I believe is a very healthy attitude about sex, and to feel beautiful and sexy.

My roommate jokingly called it “slut training” but Sherman never put pressure on me, never expressed disappointment at however long it took me to try something new, and I found myself enjoying it — it was fun. And soon I noticed my roommate was showing a little more cleavage from time to time, too, which I think was my influence.

The two lessons from Sherman that most profoundly affected my sexual future: over the course of months he taught me — no, he helped me discover — a love for sucking cock to completion, and the pleasure of having a cock in my ass. That training deserves its own write-up, in the future.

But Sherman had an ex-wife and two little kids back in his hometown, who he would go to visit every other weekend. And one of those weekends, you guessed it, my phone rang, it was Jeff, just seeing how I’m doing. We talked a little, laughed a little, and next thing you know, I said, “Hey if you’re not doing anything why not come by so we can catch up?” and within about an hour we were going at it.

I got away with it for about a month before the frequency of times I wasn’t free to see Jeff made him ask questions. I was honest about it, and turned out, after a little fit of jealousy, he was okay with it, or at least he tolerated it. He continued to place booty calls to see if I was available, and when I was, he got laid; when I was not I put my phone on mute.

So, Jeff knew about Sherman, but Sherman did not know about Jeff. And that is how it came to pass, that I was regularly fucking two very different guys, sometimes both of them in the same day, for about six months. Jeff eventually moved on, Sherman and I continued seeing each other for about another year, and then with Sherman’s encouragement, I applied and moved away to college.

Source: reddit.com/r/gonewildstories/comments/xub84w/f_two_boyfriends_too_many