by Carrie

Gender: Female
Age: 27 Now/19 Then
Race/ethnicity: White
Location: Washington DC
Highest education received: College degree (eg., BA, BS)
Occupation: Reporter
Relationship status: Engaged
Religious affiliation: Catholic
How religious are you? A little
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Straight but have experimented with a woman
How many sexual partners have you had in your life (including oral sex)? 8
How many hookup stories have you here posted before? None

My Lost Virginity

How long ago did this hookup happen? Eight 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…)? Friends With Benefits

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? Carlos was a tall Hispanic man a few years older than me (23 then). He had light brown skin and black hair, and was quite toned. He was smart which quite attracted me. I had known him for a little over a year before this, we had had a few classes together and worked on a number of projects together. We had become friends and grown quite close which was why I was comfortable approaching him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I need to share my background here a bit as part of the what led to it question. I grew up a good Catholic girl, an only child with a very overprotective single Dad. I dated very little in High School. I was also short with messy brown hair and thick glasses and a bit of a nerd. I also hated the popular hot girls. I had a few close friends who all went through puberty first and started hooking up with boys. Boys were not interested in the flat chested nerd, however I got them back as I hit puberty the summer between my junior and senior year of high school.
One day coming out of the shower I noticed I had boobs and quite a bush down there. I began to get interested in boys, but they were all terrified of my Dad. I kissed a few, made out with a few and let a few get pretty handsey. One got rough with me when I told him I wasn’t ready, but I punched him and got away. Still I was taught sex was something for procreation only and only between those who were married. I graduated High school top of my class, I know it’s a little arrogant but the fact is I am smarter than most people and boys and men find this off-putting. First year of college I was focused strictly on studies but I took a few psych classes and became very interested in sexuality.  
I wanted to have sex, but my first time needed to be with the right guy. One didn’t feel right. As I said Carlos and I were friends and he had admitted being attracted to me. I approached him about possibly being my first and he said yes.
Took about another month for it to happen, this was in the early fall of my sophomore year of college. Carlos knew he would have to be patient with me. I bought a dress, short with a flower print and showing quite a bit of cleavage. I also went to Victoria’s Secret and bought lingerie, a rather impressive 36D lace bra and panties set.
One Saturday I got dressed up, full makeup and had my hair done and lip stuck. I had never dressed up for a guy before, and when I looked in the mirror I looked like one those popular girls I hated but I kind of liked it. He had set candles up and cooked me dinner and said I looked really hot. After dinner we stared kissing and he pinned me against the wall.

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? We moved to his bedroom, and he began to undress me. He undid the ties on my dress and kissed my neck and took it off and then removed his shirt. We ended up making out on the bed and he took my bra off.  He squeezed my breasts a bit and licked and sucked them and I kind of liked it. He began to kiss me and work his way down and probably would have given me oral if I hadn’t stopped him. He then took my panties off and looked me over.
He took his pants and boxers off and I saw my first cock. He was quite well endowed and he penetrated me. It didn’t hurt, between horse riding as a kid and self-pleasure my hymen was long gone. He rode me for a while, he orgasmed before too long but kept going until I came. He then asked me to stay and we cuddled until we fell asleep. Next morning we went again, with me in cowgirl (since become my favorite position, I like being in control in the bedroom). We both orgasmed again and afterwards I took a shower before I went back to my apartment. Carlos and I talked a lot, we had the same major and a lot in common and he was also a good lover. This was one of the most memorable nights of my life.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We did discuss it, and used a condom both times. For him there had only been two other women and for me there was no sexual history. I did however make a decision to go on birth control after this.

What were your REASONS for having this hookup? I was quite attracted to Carlos and wanted to have sex for the first time.

Were alcohol or drugs involved? If so, how much? A glass of wine each

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 had to do the walk of shame across campus from his apartment a few blocks away to my dorm room. Carlos and I were what I would call Friends with Benefits for most of the rest of my sophomore year of college, until he got involved with another girl in the spring. I was a little jealous but neither of us were looking for a relationship but we wanted sex regularly and I got to learn what I liked and disliked. We hooked up a few other times when we were between relationships during college.  
I am grateful to Carlos for being my first and being so patient with me. I have not seen him in years, but he friended me on Facebook about a year ago and I saw he is now married with kids. I am happy for him.

To whom did you talk about the hookup? How did they react? My roommate found out right away, I came back into my dorm room around six the next morning and I was never out all night. She and my friends were proud of me when they found out.

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? Not at all

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 great sex for the first time and learning that sex is ok. Honestly I can’t think of anything bad about this experience. However sitting here thinking I would argue there is no such thing as casual sex, there was nothing casual about my first time. I felt a lot better about myself after this and was much more willing to have sex in the future.

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

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

Anything else you want to add about this hookup or anything else? I think I am living a little vicariously since I am do to be married in a few weeks.

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