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
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Personal support worker
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? None

My First True Sexual Experience

How long ago did this hookup happen? About a year 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 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? Sarah (not her real name) looked great. She is 33 year old married female. She had long dark brunette hair with nice blonde highlights, gorgeous eyes, truly a naturally beautiful face. She only had minimum make-up on which I love. Sarah had a nice average bust size approx 38B that was quite perky. Very voluptuous with a fairly big ass that was incredible. I have never hooked up with Sarah before. We have been chatting online for approx. 3 months on a sex chat site. I feel as though Sarah and I made an instant playful connection online and became quite comfortable from chatty about everyday life to what we enjoy/ fantasize about sexually.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? How the hookup began was over sex chatting. We developed such a strong mental connection online using erotic descriptions and sharing our real life stories that next thing we know we were arranging to meet up. The hookup began in a hotel. There was much planning involved especially on her end as she was married. I had asked her is she was really sure she wanted to meet and she said she was as she no longer had any desire for her husband and hadn’t been sexual with him in a long time. I believe she instigated the hookup but we both obviously wanted it. The lead up to the hookup was she booked the hotel as I traveled there.

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? The first time I laid eyes on her as she pulled into the hotel parking lot I was amazed. She has a gorgeous face and a playful smile to match. We got out of our vehicles and officially introduced ourselves starting with a handshake which quickly turned into a hug. We made small talk and both of us seemed slightly nervous and very excited. We both then proceeded to the hotel.
While in process of checking in, I couldn’t keep my eyes off of her. Then as I was following down the hall to our room I noticed a much older couple enter the room beside us and I was like crap… Now I’m going to feel like we will have to keep a bit quieter out of respect to them.
When we entered the room, we both looked and smiled at each other with excitement. We made small talk to get more comfortable with each other and double checked to make sure this is what we both wanted to do. She gave a resounding yes and I was def in favor as well.
To start off the evening I gave Sarah a foot massage, which apparently is the sweet spot. Sarah had informed me she has never had a foot massage outside of getting a pedicure. I then massaged her calves as I’m looking into her eyes, seducing her, slightly allowing my hand to tease higher into her inner thigh and then stop. I suggested that she should get undressed as I go have a quick shower. I though it would be best since I came up right from work and I knew the night was going to be a long one.
I return from the shower just in my boxers and see her standing there just in her bra and jeans. I walked over to her wrapping my arms around her giving her a gentle kiss on the lips. My goodness her kisses are amazing. We kissed for a little while as my hand slowly slide down the side of her body firmly cupping her amazing ass. Then Sarah removed her jeans and I walked behind her. I grabbed her from behind firmly pulling her into myself. As I gently bit into her neck she melted into me, surrendering her body to mine. My hands went exploring her body squeezing her breasts through her bra. I then I unclipped her bra and released those beautiful perky breasts. Feeling, caressing them and pinching her nipples as I kissed and bit her neck was wonderful. I felt so powerful.
After doing this for a little while, I remembered that she said she liked a little bit of aggression. So with a gentle firmness, I bent her over the bed spanking her firmly and massaging her lower back and firmly pulling her hair back as she felt my crotch press against her ass. She arched her back and let out a soft moan.
I then commanded her onto the bed where I began to finish the massage that I started earlier. Rubbing her ass, back, and shoulders as I’m straddling her, my cock is growing against her ass in my boxers. Then Sarah rolled over and we made out some more. I asked her if she wanted to see if she could win the challenge she offered earlier that day. She had said on the phone that she could get me to cum with just a bj within 5min. I added one aspect to the challenge and that was she can only do so hands-free. Fast forward the bj was amazing but I didn’t cum so doubly won…lol she was very good at oral and had excellent eye contact aswell.
We were now ready to fuck. I had got up to grab a condom and she removed her panties and I could tell she was really wet. I put my condom on and she got off the bed and bent over it. I was getting ready to fuck her doggie style. My cock is 6″ with a nice girth but with me being a big guy and her having a big ass it made it next to impossible to enter her from this position.
Guys typically always wish for a bigger dick and at that moment I really did but she was so kind about it so we just switched to the missionary position. I teased her clit with the head of my cock then pressed it into her as she slightly gasped and pulled me into her. She did not know it at the time but it’s at that point I lost my virginity. I fucked her slow and consistently as I kissed her. She was very tight. I began to fuck her harder and within about a couple minutes she began to moan nicely. As I approach the 5 -7 min mark, her moaning got to me and I couldn’t control myself and I came. It was a great feeling my cock release while in her tight pussy.
We kissed, I pulled out, removed condom, then we cuddled as the ball game was on in the background. I think she was surprised I came so quickly because I had told her a story about receiving a bj from another lady and it took her and hour to get me to cum. I told her that I’ve never been in a pussy as tight as hers and I couldn’t control myself. Her hands reached out to my face and pulled me Into her embrace. I was locked into her gaze and felt our sexual connection growing.
Within 5-10 min, I was ready for round 2. So we fucked again this time I lasted 15-20 min and I was going faster and hard which was so hot and I had pinned her wrists over her head which apparently she liked a lot. Then I came again.
We cuddled again and kissed and watched a little baseball. Then I began to tease her clit with my fingers and then I finger fucked her. I had her on the verge of cumming after 10 min of finger fucking her and my arm got tired, I was so annoyed with myself as I wanted her to orgasm to badly. But again she didn’t care. She was just happy to be having sex with someone other than her husband.
We started making out again and caressing each other and it was glorious. At this point, Sarah offered to give me another bj and she went to but apparently my dick taste like condoms and it wasn’t very pleasant so I said why don’t we just fuck again. She smiled and laid down. I put on my third condom of the evening and began to fuck her again for the third time. I had remembered about the aggressive desire she liked. So as I entered her I lean down and suck her tits hard, my teeth scratching them. She moaned so hard, I bit her neck and started fucking her hard reaching up with my hands to hold the headboard so I could fuck full force. We both loved it. It lasted about 20 min and was the best workout I’ve had in my life. We went back to cuddling and laughing. Def was the best night of my life so far

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

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? She had to get home before it was too late, and I started on my journey home. I def enjoyed the experience but I had conflicting feelings of guilt and desire to do it again. I have never met her again but we still chat from time to time. I not sure if there is a future but maybe if she is divorced, but I won’t tell her that as I don’t want her to make that decision based on me.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Sterilization, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, I was feeling lonely, Power / Dominance, Making new friends

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? No one but here. I promise to keep discretion

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? A little bit

Do you regret this hookup? A little bit

Why do you regret this hookup? Due to my upbringing, I never could have thought that I would sleep with another man’s wife

What was the BEST thing about this hookup? That she was amazing, I felt safe with her, and it was multiple rounds of fun my first time experiencing intercourse.

What was the WORST thing about this hookup? The fact that it will probably be the only time as I don’t want to break a marriage apart.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes it has. Showed me that casual sex is fun, that sex is an extremely powerful drive that can get even good people to cross there own boundaries. That how we are trained up will determined if a person feels guilty or not concerning casual sex

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

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

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I can see its benefit in meeting basic sexual needs of a person who does not have someone, or is not having that need met by there partner. The role it’s played in my life is it gave me more confidence and an opportunity to practice becoming a great lover.

What do you think about the Casual Sex Project? I really enjoy reading stories based on true experiences. Helps to see what kinds of intimate things happen out there

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