by Trudy

Gender: Female
Age: 31
Race/ethnicity: White
Location: Redding, CA
Highest education received: College degree (eg., BA, BS)
Occupation: 3rd Grade Teacher
Relationship status: In a Committed One
Religious affiliation: Christian
How religious are you? Very
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? None

Late Bloomer

How long ago did this hookup happen? 18 Months

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…)? First Time/Short Fling

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? “Glen” was a handsome sandy haired man in his mid-thirties, a few years older than me. He was also intelligent and quite charming and I was instantly attracted to him. He was a substitute teacher at the school where I teach, covering for a few months while a colleague was out on maternity leave.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Now I was still a virgin much later in life than my friends or sisters. In high school and college I was a save myself for marriage type. I dated a little, once boys or men realized they were never getting in my pants they usually lost interest. I was also diagnosed with diabetes at 19, as a side affect of that and the medication they gave me for it I had a very low libido.
I started at the grade school where I teach right out of college, and another teacher once asked me if I was asexual. I was interested in men, it just didn’t run my life. My parents and friends were always concerned that I didn’t date and one even thought I may have been a lesbian. Years went by and without even realizing it I was a 30 year old virgin.
In the fall of that year the Doctor changed me to a different medication and brand of insulin. My libido skyrocketed and for the first time I felt myself looking at men and checking them out, and I began to wonder what sex was like and what it would be like to be with someone.
Glen started subbing in late January and there was an instant connection. I hadn’t actually dated in years, I have a pretty plain appearance and my hair is usually messy and I always dress very conservatively so men seldom came near me. However Glen did ask me out to dinner after two weeks of working there.  
It took him about another month to get me in bed, despite my desire for sex and to sleep with him I was very nervous about the whole thing.  
After one of our dates we ended up back at his place making out on his couch. We had kissed before, even made out a few times but this felt right.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? 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? Glen had his shirt off, and I was down a few buttons on my blouse, just enough to where a lot of cleavage and a little bra was showing. I told him I was ready, and he scooped me up in his arms and carried me to the bedroom.  
He finished removing my blouse and then pulled my skirt down. Glen said I was pretty hot under all those ugly sweaters and I glared at him but he wasn’t wrong. He kissed me and then took my bra off and laid me down on the bed. He played with my breasts a bit and sucked on them and that felt good.  He then pulled my panties off and began to give me oral, which felt incredible. I had an orgasm which felt wonderful as it was not something I had ever experienced before. Glen then penetrated me, a little painful since it was my first time but not terrible and that felt good and he kept kissing me. He rode me until he finished and he then fell asleep right after, it took me a good long while as I was not used to having someone in my bed or being at someone else’s place.
Next morning we went again, and he talked me through cowgirl, and I rode him with his hands on my hips as support but he kept grabbing my breasts. I came first and then he did a short time after. We cuddled for a bit talking about all kinds of things I took a quick shower and then went home around noon.
I would say he was a good lover and I really enjoyed myself.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We discussed it and he was clean and insisted on using a condom even though I didn’t really want to and I had no sexual history.

What were your REASONS for having this hookup? Attraction to Glen and curiosity about sex, and I was also really horny.

Were alcohol or drugs involved? If so, how much? We had a glass of wine each at dinner.

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? The floodgates opened and I became a bit of a horny sexpot. I wanted sex all the time and was all over Glen and we had sex a lot. Even a few times in the teacher’s lounge. Went on for a few months and he transferred to another school but we still saw each other and slept together for about a month after that. He broke it off in late April, saying I had become too clingy and was getting to just be too much for him. I think it would have been a lot harder if we were still teaching at the same school.
I am grateful to Glen for being my first and if we had never gotten involved I don’t think I would have gone near my current boyfriend. I saw him recently at a school district function, another female teacher on his arm. I was a little jealous but Glen and I were friendly until my current boyfriend showed up.

To whom did you talk about the hookup? How did they react? Told my sister and a few of my friends who were proud of me. A lot of the other teachers knew as Glen and I were far from discrete.

Was this a consensual and/or wanted experience for you? For your partner? Yes for both of us

Do you regret this hookup? If so, why? Hardly at all, my only regret is that my current boyfriend was not my first.

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? Having sex for the first time and really enjoying it. Other than what I mentioned not sure there was truly a bad part. I learned sex is ok and that I really like it. I am also a lot more self confident now and was a lot more open to sleeping with my current boyfriend the first time.
One thing did change during the hookup, I started to dress differently. Thongs instead of granny panties, lower and lower cut tops and even a few short skirts. Part of me liked the attention from men, until a parent complained and the Vice Principle told me to change how I dressed. Ironically enough, the parent who complained is the dad of a now former student and the man I have been seeing for more than a year and am currently living with.

All things considered, how POSITIVE was this experience? Very positive

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