First Time With a Woman

by Gene

Gender: Female
Age: 41
Race/ethnicity: Mixed
Current location: San Fransisco
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Company Vice President
Relationship status: Seeing Someone maybe seriously
Religious affiliation: Lapsed Catholic
How religious are you? Not at all
Sexual orientation: Bisexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? One

First Time With a Woman

How long ago did this hookup happen? 23 Years

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 of More

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? I’ll call her Amy, she was a pretty brunette two years older than I was (I was 18 she was 20).  She was fit with a few tattoos and a chest a bit bigger than mine.  She was the roommate of a girl I befriended freshman year of college and even though Amy was a year ahead of me in college she was still in two of my classes and we shared a lab time.  I found her intriguing and was quite attracted to her but my sexuality was something I was very much struggling with at the time so it took a few months for anything to happen between us.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I feel some background is in order with this post.  I grew up in a small town in a large Irish Catholic family.  I had a strict, religious alcoholic father (he got sober when I was 11 but fell off the wagon twice when I was a teenager) who was very controlling.  I also struggled with my sexuality in High school, going through puberty and finding that I was attracted to both boys and girls.  I also grew up being taught homosexuality was a sin.
I had the same boyfriend for most of high school who was very understanding of this, not that he and I never had sex because trust me we did plenty.  I also dated and lived with him for two years in my late twenties.  Moving back since it was such a small town and also the early 90s when such behaviors were not near as tolerated as they are now I had to keep my urges a strict secret.  The closest I came was making out with one of my fellow cheerleaders at a party and maybe we would have gone further had we not been interrupted.
So I go to college and am away from home for the first time and I cut loose.  I got a tattoo, smoked a little weed, drank a little but because of my Dad I have hardly ever touched alcohol and I also slept around a bit but all with guys.
I actually met Amy my second week of college, as I said above she was the roommate of a girl I had become friends with.  I was attracted to her but still struggling with my sexuality so nothing happened right away however there was a little flirting and some light touching.
It was early in my second term, and Amy came to my dorm room so we could work on a project.  Its been a long time so I don’t remember exactly what happened but I believe we brushed up against each other and started kissing.  I gave in and decided to let this happen.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? This has been a lot of years and many partners ago so bare with me here.  Amy put her hands down my pants and played with my vagina.  Clothes came off and we made out naked for a while.  I played with Amy’s breasts and sucked on them a little and she did the same with mine.  I do remember she was eager and enthusiastic and also shaved in the vaginal area something I had never thought of doing and was different back then.
Amy was fingering me through most of it and then moved and began to give me oral, the first person to go down on me.   It felt incredible and she was quite good at it.  She gave me a rather intense orgasm and afterwards we cuddled for a while and talked.  I mentioned my struggles with my sexuality and my attraction to both guys and girls and Amy admitted to dealing with the same, but she had been able to explore them more in High School and that they were ok  We talked about all kinds of other things until we fell asleep.  In the morning Amy got dressed and gave me a kiss goodbye before leaving

Did you have an orgasm? Did your partner(s)? I did and Amy didn’t

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None and we never talked about it

What were your REASONS for having this hookup? I was very attracted to Amy and had never been with a girl before.

Were alcohol or drugs involved? If so, how much? No

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? I hooked up with Amy a few more times in the following weeks and off and on through college and for about a year after when we were between relationships.  It was a lot of fun and Amy helped me get comfortable with being bisexual.  We kept it discrete as it was over twenty years ago and not now.  I finally stopped seeing her when I met my first husband and she moved to Europe shortly after.
I ran into her brother at a conference last year, he knew about us, he told me Amy still lives in Europe and is now married with two kids.  Personally I am grateful to her for being my first girl and helping me learn what being bisexual is.

To whom did you talk about the hookup? How did they react? Told a few people and partners over the years, a few had been curious.  Most were not surprised.

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

Do you regret this hookup? If so, why? Not one bit

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? I would say the sex, but I think the best part was learning about and coming to terms with being bisexual (I consider myself pansexual now, back then there was no term for it).  Since then I have hooked up with and dated both men and women and even openly in recent years.  My parents and a few of my siblings still have no idea about me though.  Sexually I consider this experience not so much as casual as very formative.  I was much more comfortable and sure of myself once I learned I was bisexual.

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

All things considered, how NEGATIVE was this experience? Not at all negative

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