Age: 35 now/19 Then
Highest education received: Post-grad
Relationship status: Single
Religious affiliation: Catholic
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 22
How many hookup stories have you here posted before? A Few
How long ago did this hookup happen? 1998 and into 1999
How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Affair
Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Kim was a striking woman in her mid thirties, short but with a big chest and raven black hair in what would be called a pixie cut today. She was one of my professors, I had taken a few of her classes over the previous three years but I did not know her well. I had thought this was a hot woman and was sometimes distracted by her looks when she was giving a lecture.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? In High School and college I focused mostly on my studies (see My Son’s Mom) and grades and I was also younger than many of the other students. I did notice girls but I was nerdy with glasses and they mostly paid me no heed. Other than one rather clumsy night with a fellow student (might share that story even if it is embarrassing) I had no sexual experience.
It was in October a few weeks into my third year of college. I was already closing in on my first Bachelors degree and Kim had been assigned to supervise me and my research for my thesis. I had been meeting with her heavily since the summer, a lot of private time in her office and late in the evening meetings. I was presenting her with my latest findings, we were both sitting on the couch. I can remember thinking she smelled really nice that day, her perfume, and also thought how tight her shirt and pants were. Thinking back she had bent over a few times and leaned over to make sure I got a good view down her shirt.
Kim put her hand on my thigh stopping me midsentence and then moved it over and stroked my cock through my pants a little. She then leaned over and kissed me full on and then took my hand and pulled me to my feet. She put my hand on her breast and asked if I liked it, and I nodded. Next she took my hand again and this time stuck it down her pants and placed it on her vagina and again asked if I liked what I felt and I again replied yes. Kim then asked me if I had ever had a woman before and I said yes, to which she replied I doubt that.
Kim pushed me back down on the couch and then sat on my lap and straddled me and stuck her hand down my pants and began to stroke my cock. She gave me a hand job and kissed me a few times and I grabbed her ass a little but she always stopped me whenever my hands got more than a little above her waist.
I came and Kim climbed off of me and I sat there for a minute. She went to her purse and got some hand sanitizer. Eventually I stood up and put my hands around her waist and kissed the back of her neck a little. She finally replied “Not here.”
Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We drove to a small hotel the next town over, about forty minutes away. My anticipation was growing at what was coming. Kim was friendly with the staff and I quickly figured out that I was not the first she had brought someone here, but I simply did not care. We went to our room, she had requested one in the back. I don’t really remember the room much, other than it had a large bed and a shower. She closed the door and we started kissing again and I can remember pinning her against the wall. Kim finally moved me towards the bed, and said I could do whatever I wanted with her as long as I did not get rough. I said I wanted to undress her and she agreed, as long as whatever I took off her she then got to remove.
I took my shirt off first and then removed hers. I remember she had a black bra on. I then pulled her pants off and Kim did the same for me. Next I wanted to remove her bra and reached around back and she laughed a little, it opened from the front which she did. Her beasts popped out, they were huge ( I would learn they were DDs when I went to buy her some lingerie a few months later) and had been an attempt to get her inattentive husband’s attention about a year before. This was my first encounter with fake breasts, and truly my first real encounter with boobs period. She let me play with them a bit, and then lick and suck them. Finally I removed her panties and she was standing there nude. Kim was the first woman I saw naked (the other had been in the dark and she never did take her shirt off) and I felt my heart stop. Despite being 35 she never had had kids (another problem with her marriage was her husband could not give her any) and everything was very firm and she also had a great ass. She was very fit and toned from jogging.
Kim asked if I would follow her lead a bit. She laid down on the end of the bed face down and put her ass up and brushed it against my cock a few times. I didn’t know this was doggie style she wanted then, finally she told me to move forward a bit and she used her hand and stick my cock in her vagina. She then told me to put my hands on her waist and go as hard as I needed. I did, and I will admit she had to put me back in a few times but towards the end I had it down and was really enjoying myself and from her moans Kim was too. I came and had to lay down.
Kim wanted to cuddle a bit and laid her head on my chest. She was a small woman really and fit next to me in bed perfect. After half an hour or so she moved down and began to lick my balls and suck my cock. I had never had oral before and quickly began to enjoy my first blow job. Back then I could get it up at the drop of a hat or the slightest patch of bare skin. I came in her mouth and Kim had to go rinse her mouth out.
She returned and laid down next to me in bed. Kim said she knew I didn’t have a lot of experience but she was determined to get me to please her. After a while she asked if I wanted to go again and I said yes. This time we did standard missionary and I entered her and used the backboard as a brace. I kissed her throughout and after a while she began to moan loudly and her skin was flushed and her eyes were rolling back in her head. I would only later learn this was a woman having an orgasm and shortly after I came. At this point it was well into the a.m. and we were both really tired and fell asleep.
I awoke to find she had mounted me in what was the best wakeup call ever. I put my hands on her waist and eventually grabbed her breasts hard. We orgasmed in near unison this time, a very special moment, and then relaxed for a bit. We took a shower and had shower sex, fulfilling a fantasy I had had since I was fourteen.
We checked out of the hotel a little after noon and Kim drove me home. She gave me a very passionate kiss, and told me we could continue on two conditions, told no one and was exclusive to her. I agreed. Kim was a very great, and patient lover.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used condoms and she showed me later that she had been tested clean. Eventually a month or so later Kim went on the pill.
What were your REASONS for having this hookup? I was young and eager to explore my sexuality.
Were alcohol or drugs involved? If so, how much? Not for me but I would later learn Kim had smoked a joint in the afternoon before because she said it calmed her down and made her horny. However as far as I am aware there was no other drug use the rest of our affair.
What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Kim and I had an affair that lasted the rest of the school year, I use the term affair since she was married. I experimented with her quite a bit sexually, she was open to almost anything non-violent and we tried a lot of different positions. I learned I really enjoyed oral and girl on top is my favorite position. I also learned women can enjoy sex as much as men. Kim actually put on a little weight because many of her jogging mornings were stopping by my place and hooking up before classes. I also learned I liked a bit more curves on my women. Trust me though, waking up to her sitting on the end of my bed in tight jogging shorts and a sports bra was great.
I gained a lot of self confidence from this relationship. I admit I developed strong feelings for Kim but she would never leave her husband.
The school year ran out and Kim informed me we would not be resuming in the fall. I will admit I was crushed and a little naïve not to expect it. That summer I had a fling with a friend’s sister while on the rebound, my first such hookup. Kim had opened me up to sex in general, I like to think of her as my sex professor.
In the fall things were very awkward, and I avoided signing up for any of Kim’s classes. I ran into her in the hall a few times and while she was friendly I was not so much. I would later learn she had quickly taken up with another one of her students, and eventually one of my friends later in the year. He told me bragging, not knowing Kim and I shared a history. I was very angry with her about this.
Eventually Kim and her husband split a few years later, one of her boy-toys had knocked her up. She left the university shortly after and last I heard she was teaching on the West Coast, we ran into each other at a conference a few years back. Overall I look back on my time with Kim fondly, and I am very grateful to her for opening me up to the world of sex.
To whom did you talk about the hookup? How did they react? My roommate knew as she often came to my place in the morning. He was impressed with me and jealous. My one friend knows, the one she was with after me. Other than that I have only ever told a few people.
Was this a consensual and/or wanted experience for you? For your partner? For both of us very much.
Do you regret this hookup? If so, why? A little because she was married and I felt very guilty about that for a long time. It’s not a line I would cross now, less about morality as I have gotten older but just because it’s such a pain in the ass.
What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? A lot of sex and learning what I liked and didn’t like. Worst part was she was married, and as I said I felt guilty for a long time. This was my first real sexual relationship and opened me up to it and made it to where I could approach other women. I gained a lot more confidence and learned there was life outside of my studies.
All things considered, how NEGATIVE was this experience? A little negative