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What’s your gender? Man
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? South Florida, USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? IT
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50, 55-60 if counting oral
How many hookup stories have you here posted before? Lots

Southern Belle’s Virginity

How long ago did this hookup happen? When I was 19 or 20

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than 6 months

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? “Sara” was a Southern Belle from Georgia or Northern Florida, not really sure. I met her during my sophomore year at University through a mutual friend. My friend was the lighting designer of the school’s theater department and Sara was an aspiring stage actress. She had strawberry blonde hair, bright blue eyes, incredibly fair skin, average breast-size, and an average ass. Describing each of her features, I would have to keep saying “average,” but when it was all put together, she was pretty cute. I think I was a bit more attracted to her because of her genuinely sweet personality. She was as sweet as anything and completely down to earth.

Sara would stop by my dorm room every so often with one of her acerbic friends, seemingly just to say hi. I figured one of them might have had a thing for me, but wasn’t sure which one it was. They were both decent looking, so I was ready to accept the advances of either one whenever they showed their cards. With time, it became clear the Sara was the one who had a thing for me. Her friend was always talking her up, trying to get me to agree, and abruptly “leaving” to go do something.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Once I knew Sara was interested in me, I started flirting with her more openly. Pretty soon when she came to visit, her friend was no longer accompanying her. Through more conversations, I learned that Sara was a virgin but not necessarily intending to keep it for any special occasion. Near the end of the fall semester when some people will still taking exams but before everybody was going home for winter break, Sara came over and, like usual, and sat on my bed (not many places to sit in a dorm room). Even though she had a crush on me, Sara must have known deep down that I wasn’t interested in a relationship. Each time I flirted with her, she would flirt back, but never really allowed me to act on anything. On this particular occasion, she finally broke down and allowed me to kiss her.

Our kissing quickly became more passionate and, after making out for a while, we laid down with one another- Sara being on top- and started to grind into each other. I’m not sure if it was because she was a virgin, but Sara was getting way, way more turned on that what I would have imagined just from us rubbing against one another. I have to imagine she never masturbated in her life- that assumption would align with her personality perfectly, so I can only imagine how much pent up sexual frustration she had.

Just as the body temperatures started to get really high and the instincts were lovingly clouding our judgment, Sara had a moment of clarity and abruptly told me that she had to leave, using a tone of voice that indicated to me “I want to stay, but I should really go.” However, before she could leave, I took her car keys. I playfully told her that she wasn’t going to get them back unless she went down on me. She hesitated…and smirked.

Sara pretended to put up an argument, trying to get her keys back without having to go down on me, but it was obvious from her constant smirking and sideways glances that she really wanted to do it. I felt as if I was giving her an excuse to do something slutty that she really wanted to do but her personality by nature thought was too naughty.

With a bit more prodding, Sara pulled my comforter over her head and my body and disappeared from my view. I felt her undo and open my belt, unzip and open my shorts, and pull down on my boxers. There’s something wonderfully indescribable about your dick being freed by a girl who wants it. And it was absolutely heavenly when I felt her lips wrap around the shaft of my cock.

Sara sucked and stroked for about five minutes before asking me, “is that good enough?” to which I replied, “have I cum yet?” I wasn’t very nice to her; but my being an asshole was generally in jest. Women seem to respond well to that. Anyway, Sara sucked and stroked for a little while longer, eventually removing the comforter so that I could watch her head bob up and down. She did something I can only imagine she thought was devious and made eye contact with me while licking up and down my shaft. Her blue eyes were piercing.

It was clear Sara wasn’t going to make me cum, so I let go of her car keys and told her we should have sex. She told me that she really did need to leave because she was supposed to be studying for an exam. I accepted her excuse, begrudgingly let her leave, but made her promise to come see me again when she had the time.

Now that I knew Sara was a virgin and she had given me a taste of what she was willing to do, I couldn’t get her out of my head. I started initiating conversations with her- something I hadn’t done much before.

True to her word, Sara came back just a few days later right after her exam. She told me that the exam was easy- and she was glad- because all she could think about was coming to see me and letting me fuck her brains out?

What?! Oh, man. I heard correctly. She wanted me to take her virginity.

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? I asked her a few times if she was sure about her decision and she affirmed that she was. Not wanting to talk her out of it, I undressed her and took my own clothes off. She stood there in front of me looking like she didn’t know what to do next. I just stood there for a minute staring at her naked body. She had extremely fair skin and decent breasts, but just the fact that she was stark naked in front of me was more than enough to get me extremely turned on.

Sara sat on the edge of the bed, switched between staring at my face and my dick as I walked over to her, and she began to suck my cock. When I was made fully erect, I rolled on a condom and placed myself on top of her. Her face was “concerned.” She didn’t seem like she was second guessing herself, but you could see in her eyes that she knew this was “a big deal” and something she’d probably remember forever. Me, I was just happy to get to take my third girl’s virginity.

When I put the tip of my dick against Sara’s pussy, her face scrunched up in anticipation of pain. I told her that she needed to relax and stay loose, otherwise it was probably going to be a lot more difficult for me to enter her. She tried her best, but each time I thrust forward just a little bit, Sara would tighten up. She was really nervous about it hurting. It took us at least 15 minutes for me just get my dick about a quarter of the way into her. When I finally felt her hymen pressing against me, I told her this was the part that might hurt the most. She looked terrified. I asked her again if she wanted me to keep going and she nervously nodded up and down.

I thrust. She gasped. Still not broken through. I thrust again. She screamed, tightened up, and pulled her hips away from me. I told her that this wasn’t going to work if she keeps tightening up and backing away from me. She apologized and instructed me to try again. I tried…and tried…But each time I made the slightest thrust toward her, she winced in pain and backed up. After quite a long time of trying, I had completely lost the mood. I only had about half of my dick inside of her and I was beginning to lose my hard-on.

Eventually, I gave up. I told her that we should try again next time. She apologized a lot, telling me that it was a lot more painful than she anticipated, but was glad that we were trying. I, somewhat annoyed, didn’t do much to comfort her and she wound up leaving.

How sexually satisfying was this hookup? A little

Did you have an orgasm? No, not even close

Did your partner have an orgasm? No

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? In my mind, since I never broke through her hymen, I didn’t really count it as having had sex with her. Sara on the other hand was telling some of her friends how she finally lost her virginity and that I was the one who took it. I was sort of embarrassed that she called “that” sex, but ultimately figured on some technical level my penis was (partially) inside of her vagina.

After we came back for the spring semester, we didn’t see each other again. My attention was aimed at other girls I was sleeping with/pursuing and Sara must have known that she wasn’t going to be able to tie me down.

Ultimately, we never hooked up again. She still sees me as the guy who took her virginity; but, I sort of just see her as a girl I “sort of” had sex with.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, I was feeling lonely, Power / Dominance, It was easy / convenient

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I didn’t tell anyone. But a few of Sara’s friends told me “I heard you took Sara’s virginity.” I had to awkwardly explain to them that it “sort of” happened.

How would you best summarize people’s reactions about this hookup? Other

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I guess, technically speaking, Sara was the third girl whose virginity I took. That’s something I get off on: knowing she’ll always remember me as the first guy to fuck her (no matter how terrible it really was).

What was the WORST thing about this hookup? I never got my dick fully inside of her. I don’t even know if it was halfway. I didn’t even pop her cherry! And, I never gave myself a second chance to do it properly.

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

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

You have a hookup story to share? Submit it here!

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