Not So Prude After All

This post is sponsored by Trust Massage Oil.


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? Tons

Not So Prude After All

How long ago did this hookup happen? About 10 or 11 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

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

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? While home from college one summer, I went to one of my co-worker’s house parties while his parents were out of town. There were a ton of people at this party, but there was one girl in particular who I couldn’t keep my eyes off of. She was around 6′ tall (I’m 6’3″), had dark brown hair, dark brown eyes, an Italian bronze skin tone, and absolutely enormous breasts. Her body was quite toned and athletic, but I have to admit she had a tiny bit of belly (which she hid well with her clothes).

When a few of my friends/co-workers noticed me checking her out, they told me not to waste my time. She was apparently extremely prude and didn’t give the time of day to anybody. I kept checking her out, waiting to get noticed, and hoping to make some of that “I want you” eye contact. Sure enough, after our eyes met for the first time, we continued to give one another glances across the room quite frequently.

I was convinced that my friends had to have been wrong. Perhaps, I told myself, they went after her and she had rejected them. There was no way I was going to not try and get with this girl…she was just my type. I decided to ask the host of the party who she was and he proceeded to tell me that she was the daughter of his parents’ friends. Her name was “Andrea” and they had become friends because of their parents. I asked him about her reputation being prude and he told me that it was entirely accurate. He’d never seen her with a guy who give the slightest attention to anyone.

So why was I getting the “I’m interested” eyes? I had to find out.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Unfortunately, just as I was about to make my way over to Andrea, her friends scooped her up and headed toward the door. As she walked out, she looked back at me and gave me a very small shrug as if to say, “You had your chance – you blew it.” I was really disappointed that she was leaving, but I was now determined to know what she looked like with her clothes off.

A few days after the party ended- and not having any way to contact Andrea- I decided to add her on Facebook. She accepted my friend request and I sparked up a conversation. When I got around to asking her out, she played hard to get, but ultimately agreed to allow me to pick her up one night during the week.

We didn’t have any particular plans regarding what we were going to do, so this lead me to believe that perhaps she wasn’t as prude as everyone thought.

That night, I got ready and took the long drive to her place down by the beach. She looked stunning. She wore a loose and flowing dress which had a deep v-neck and tiny straps over her shoulders…and high heels. The first thing she told me was “I’m so glad you’re still taller than me,” referring to her heels. When we got in the car, Andrea suggested we go down to the beach. I wasn’t sure if she was leading me toward a populated area with shops, entertainment, and nightlife…or if she was directing me toward a dark and secluded place. But, not wanting to spoil the surprise, I just followed her directions.

Once we got to the beach, I already knew I was going to get laid. This was a dark, secluded area and there weren’t even any street lights anywhere. There’s no way she wanted to come here and not expect me to try and put the moves on her. So after we got out of the car and made our way to the sand, we headed for a raised, wooden lifeguard stand where we could have a bit of privacy on the off chance somebody did show up.

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? At first, Andrea sat next to me and we made small talk. But after some corny jokes and not-so-subtle direct flirting, we started to make out. Her face was gorgeous; her tits (which were already huge) were pressed up tight; and her lips were large and soft. I pulled her close to me and eventually guided her to sit on top of me, straddling me. I wanted to see if she would keep her crotch raised in the air by supporting herself on her knees, or if she would allow herself to put her weight on me, thereby pressing her crotch into my hard cock.

She pressed herself into me.

We continued to make out and I pulled the straps of her dress off of her shoulders. I maintained eye contact with her as I pulled her dress down, not wanting her to feel like I was only interested in her body. I think it’s little things like this that make a girl feel wanted and not cheap or being used. Anyway, it worked. After a few seconds of having maintained eye contact she said something to the effect of, “My tits are an inch from your face and you haven’t even looked at them yet? Impressive.” Having made my point, I said something snide like, “I can only hold out for so long,” and took a long, hard look at what was in front of me.

My. fucking. god. She had the type of tits that hung low. Not the saggy kind, but the kind that would sway magnificently if you were to fuck her in a doggy style position. I would guess a 36 D. They were pale, which was quite the opposite of the rest of her bronze body, and she had puffy, pale nipples which were just a shade pinker than the pale breast around them. I took both breasts in each of my hands, massaged them, kissed them, sucked them, and grinded my cock into Andrea’s pussy. Given that she was wearing a dress and straddling me, the only thing between us beside her panties was my boxers and jeans. It was safe to say she was getting extremely turned on.

After this first step of foreplay, I started to undo my jeans so I could slide it up into Andrea’s pussy. I wasn’t 100% certain she was going to allow us to have sex and it didn’t help my confidence when she climbed off of me once she saw me undoing my jeans. Fortunately, she wasn’t climbing off to prevent the ensuing fuck-fest, but instead she was taking a seat next to me again so that she could lower her face into my lap.

She kissed me passionately and grabbed my cock. I was lost in her eyes until her head turned away from me and lowered into my lap. She put my dick into her mouth and gave me a wonderful blow job. She used a lot of saliva, making it quite messy and lubricated, and quickly climbed back on top of me. She slid her panties to the side, grabbed me once again, and slid me into her pussy. So warm. So tight. It took her a while to lower herself onto me, but once she had done so, I was surprised that my dick was absolutely all of the way in her. I guess I had been used to fucking shorter girls who couldn’t take the entire length of my dick, so it was a pleasant surprise that along with Andrea’s height came the ability for her to take my entire cock into her pussy without feeling any pain.

Being in control, Andrea slowed bounced up and down and rocked back and forth. Her tits swayed when she rocked and jumped in small circles when she bounced. She kept her body upright rather than holding on to me, allowing me to watch myself slide in and out of her and allowing me to watch her body as she orchestrated her movements. It was a beautiful scene.

After what felt like a respectable amount of time, Andrea started to squeeze her thighs. She shut her eyes tightly, moaned with pleasure, and thrust into me slower- but harder- than the rhythm she had been. She came. After sitting there with me still deep inside of her for a few minutes, she finally slid off of me and had a look of pure satisfaction on her face.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, not even close

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? After sliding off of me, Andrea sat back next to me and put her head on my shoulder. She asked if I wanted a hand job since she wasn’t too keen about putting my dick in her mouth while her pussy juices were still on it. I appreciated the offer, but I knew she wouldn’t be able to make me cum by stroking me, so I told her not to worry about it.

I finally got the courage to ask her about the party. She told me she wanted me right then and there at the party, but she had to leave. I told her I had asked around about her (she blushed and smiled) and that I had heard she “wasn’t receptive” to guys. I tried to phrase it politely. She let out a laugh and said, “well not to just anyone” as if that settled the matter.

Externally, I commended her for being particular about who she was intimate with. Internally, my ego was inflated that I was the type of guy she was interested in.

After dropping Andrea off at home, we remained friends on Facebook for several years, but never really chatted much again. We both had received what we wanted and I guess neither of us cared too much whether or not it happened again. For me, at least, there were too many other prospects out there to continue sleeping with somebody whom I had already been with. But, now, years later, looking back, I would have liked to have slept with her more times than I did. A pair of tits like hers doesn’t come around often.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Thought it was an important experience to have, To feel more desirable, To feel more confident, Power / Dominance

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? It didn’t need to be said verbally. It was obvious we both wanted each other.

To whom did you talk about the hookup? How did they react? I never wound up telling my friends about sleeping with Andrea. They were good guys and I didn’t want to make them feel bad that I was able to sleep with a girl they had all tried to get with at one point or another.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? Andrea’s boobs were definitely top three all-time in my library of women.

What was the WORST thing about this hookup? I was too short-sighted and young to realize what an incredible body was before me. I should have made the most of it and continued to see her all summer. I would have loved to keep fucking her.

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

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

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