Your First Time Should Be Special

by ty

What’s your gender? Man
How old are you? 30
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Some college (not currently in college)
What’s your current relationship status? Single
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)? 20+
How many hookup stories have you here posted before? 1

Your First Time Should Be Special

How long ago did this hookup happen? 11 years

What was your relationship status at the time? Single

How would you best classify this hookup? First of Many

How long did you know the person before this hookup? For less than a month

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? She was a year younger than me, long blonde hair, blue eyes, average height and very thin, she weighed maybe 100lbs but she had huge tits. Aside from her seemingly shy personality, she had a reputation as a slut. I’d met her through a friend and we’d started hanging out and being a virgin at the time, I was hoping she’d put out.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My buddy was having a big party at his parents farm so I invited her out, she knew a few people there but she stuck pretty close all night, she had to work the next morning though so she said she couldn’t stay out too late, around 11PM she asked if I could drive her home. I was a little buzzed but some of the guys were egging me on telling me to take her home and make a move so I went for it. It was a short drive to her parent’s place, she told me to park down the road so I didn’t wake them up. We said goodnight when she came in for a hug but I kissed her and much to my surprise she kissed me back. I was a little over eager and started rubbing her inner thigh, that’s when she stopped me and pulled back, then she tells me one of the guys had told her I was a virgin and she should help me out. I didn’t know what to say but she continued on saying I was cute and all but my first time should be special and not just a random hookup. I gave a weak attempt to talk her into it but she insisted it wasn’t happening. I admitted defeat and said goodnight, there was a slightly awkward silence as she went to get out then she looked back at me and said, “Damn it, I don’t want to send you back sad, I suppose I could give you a blowjob?” I gave her an excited look and she closed the door and told me to fold my seat back.

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 eagerly dropped my seat back as she tied her hair up in a ponytail and leaned over to me, I was already getting hard as she undid my jeans and pushed them down, then she pushed down my boxers a bit reached in and pulled out my semi-hard cock, it continued to swell up as she held it and mumbled, “What the fuck?” a little concerned I asked if something was wrong. She giggled and said, “Not at all honey, It’s just, your cock is well, big”, then she leaned over and took it in her mouth, it felt better than I could have ever imagined as her head began bobbing up and down, she grabbed my hand and put it on the back of her head, I pushed her head down as she swallowed me deeper and deeper, it only took a few minutes and I could feel it building. I warned her that I was close but she just kept going, I tried desperately to hold off but it was no use, I let out a groan as my hips thrust upwards and my cock throbbed as it erupted in her mouth, it finally passed and I relaxed back into my seat as she came back up and swallowed. She sat back in her seat and asked, “So, do you have condoms?” I gave her a curious look and nodded yes, she gave me a smile and said, “Well then I guess tonight’s your lucky night, let’s go somewhere a little more private”. She told me to drive to a little park down the road. When we got there we climbed into the back seat and started making out, then began removing each other’s clothes, I was speechless when she removed her bra, her tits were huge but firm and round, we fumbled around as we removed our pants, I was already hard as a rock so she grabbed a condom and rolled it on and straddled onto my waiting cock. I let out a soft moan as I parted her warm wet lips, she moaned in my ear as I slipped inside her pussy, she started riding me faster and harder, her big firm tits bouncing in my face, all I could think was thank god she gave me a blowjob first, luckily it only took her about 5-10 minutes to reach orgasm, the second I felt that pussy squeeze me I pulled her down tight and blew my second load of the evening. We got dressed and I dropped her off.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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? I was as happy as could be the rest of the weekend, the next day she texted me saying she wasn’t really interested in dating but she thought I was cute and she thought I had a big cock so she’d be more than willing to carry on as friends with benefits. We carried on for several years until she got a serious boyfriend.

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, Learning new things, experimenting, Intoxication

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

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? I don’t know / I’m not sure

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

To whom did you talk about the hookup? How did they react? buddies

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

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? losing my virginity

What was the WORST thing about this hookup? 10 yrs later I now work with her husband, she’s settled down in the role of sweet innocent housewife. Meanwhile, all I can think about when I see her is how much she used to enjoy me blowing loads in or on her.

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

All things considered, how NEGATIVE was this experience? A little negative

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