Double Penetration For Laura Ashleigh

by Vacationing

What’s your gender? Man
How old are you? 33
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Architect
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Sexual
How many sexual partners have you had in your life (including oral sex)? Maybe 25
How many hookup stories have you here posted before? 0

Double Penetration For Laura Ashleigh

How long ago did this hookup happen? Two days ago

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Group sex

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? My fiancé Laura Ashleigh is tall and slender with B cup tits and an incredible bubble butt. My friend Gary is about the same height as me, 6’ tall, and has a thin build.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Several friends, my fiancé, and I went to the Florida Gulf Coast for the weekend while prices were still cheap. There were six of us: three guys and three girls. L. A. and I were the only couple. We rented a two bedroom house a few blocks from the beach with a large sectional couch from Thursday-Sunday.

Basically, after a night of drinking and later partying at the house, one of the girls hooked up with one of the guys, and they got the other bedroom. Originally, it was L.A. and I in the master, Pete and Dave on the couch, and Jen and Sarah in the other bedroom. We were the first to go to bed, and about 20 minutes later, Gary came into our room and said that Dave and Sarah were hooking up and went into the spare room and that Jen was uncomfortable sharing the couch with him. So, he was asking if he could sleep on our floor. Initially, I asked him to sleep on the living room floor, but he and Jen had been clashing all night and he said, “Please? I don’t want to keep fighting with her all weekend!” So we relented. The bed was a huge California King, so we agreed that he could sleep in the bed and that I’d be in the middle. Gary jumped in and almost immediately passed out while L.A. Jumped in the shower and got ready for bed; I sat in bed playing games on my phone.

When Laura Ashleigh came to be, she was wearing sweat shorts, no bra, and a wife beater. I just wanted to pass out, but she kept teasing me. She kept wanting to make out, and I kept saying “Gary is in the bed!” But she was slightly drunk and wouldn’t stop. She grabbed my dick and said, “It’s fun watching you squirm!” Before I knew it, we were making out, and she was squeezing my now super hard cock. I slid my hand down her pants and could see that she was super wet and began lightly rubbing her clit with my index finger. She was trying not to moan and was now trying to pump my cock without shaking the bed too much. Gary was halfway snoring. She whispered, “Put your fingers inside of me.” I didn’t, and I just kept lightly playing with her clit. When it seemed like she couldn’t take it any longer, I pulled her hips next to mine while facing her, pulled her shorts and panties down just far enough to put my cock between her legs on the outside of her pussy, and began slowly grinding. She started saying things like “I want you to fuck me,” “take me in the bathroom and fuck me in the shower,” and “fuck me on the floor now!” I reached down and slid her shorts and panties off and threw my boxers on the floor. As she turned to get out of the bed, I grabbed her hips and slid my cock inside of her and thrust slowly for a minute. L.A. said, “Oh my god,” and pressed a pillow against her face to muffle her moans. I began thrusting harder and faster and Laura began pushing back against me.

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?  After several minutes of this, I got up on my knees and began fucking her full doggy style. I wrapped my arm under her and pulled her up so her back was against my chest and began kissing the back of her neck. Gary halfway woke up annoyed and jerked over on his side pulling the covers all the way off of us. She said, “Shit, Gary!!” And said that we should get on the floor. I said, “You started this,” and grabbed her wrist and put her hand on Gary’s crotch. She jerked back and said, “What the fuck are you doing?” I kept fucking her, softly kissed the back of her neck, and said, “Now who’s squirming?” I grabbed her wrist and guided her hand back to Gary’s crotch and said, “It’s okay.” She began unbuttoning his shorts and said, “This is scandalous,” but she didn’t stop. After a few minutes, Gary was awake and getting a handjob while I fucked Laura Ashleigh hard from behind. At some point, I grabbed her left wrist with my left hand and pulled her against me as my hips slapped against her ass. With my right hand, I grabbed her by the back of her hair and guided her face over to Gary’s cock and began pushing her head up and down. She began moaning loudly and came almost immediately. After she came, I pulled out of her and told her to straddle Gary, and she did (in the reverse cowgirl position). I watched her ride him for a minute, which was super hot, and then stood up and put my cock in her mouth. I have been with L.A. on and off over a ten year period, and she didn’t like giving blowjobs. She would always use the excuse that I was too big and that it hurt her jaw. But now, she was giving me the best head she had ever given, and I had ever gotten. She was moaning, sucking, cupping my balls, and taking my cock all the way to the back of her throat. It was amazing seeing how turned on she was and seeing what she was capable of. She came while grinding hard on Gary, and I had a hard time not exploding in her mouth while she was cumming. When she was done, she fell forward and said, “That was amazing!” Gary spun her around to face him, pulled his arms under her shoulders, pulled her close to his chest and kept fucking her.

I got up, grabbed a tube of lube and her little travel vibrator from her bag, and came back to the bed. I lubed up my cock and her ass. I slid my cock in her ass crack and slowly began rubbing it against her asshole. She began saying, “Omg, what are you doing? What are you guys doing to me?” Up until this point in our relationship, there had been absolutely zero butt play. It had strictly been “off limits.” I rubbed my head back forth over her ass and slowly pressed it inside, pulled out, then repeated pushing it in deeper each time, until all of a sudden I slid past my head and down my shaft until she wrapped tightly around me. When I entered her, she sat halfway up, arched her back, gasped and moaned, “Oh my fucking god!” I could feel Gary’s cock sliding in and out of her pussy. Concerned, I asked, “Is this okay,” to which she replied, “Fuck me!” Almost immediately after this, she came hard and uncontrollably! I could feel her muscles grip our cocks with each wave! Over the next five minutes, she came at least another three or four times. During the last time, I couldn’t restrain myself, and I came deep in her ass. It was a huge orgasm. In the middle of it, I heard Gary murmur, “I’m coming,” and he came in her pussy. Laura Ashleigh rolled onto our side of the bed, and I got up and got her a towel. While I was doing this, she told Gary to go sleep in the other room.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

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? When I came back from the bathroom, L.A. Seemed freaked out. She asked me if I thought she was a slut and if I was sure I still wanted to marry her. I could tell she felt super guilty. I told her that I absolutely still loved her and that it was okay. I also noticed that she was weird around Gary for the rest of our trip. We hooked up again on Saturday, which was our last night there, and afterward, she admitted that while having the threesome she had never had that many orgasms before and that she couldn’t stop things about how good it felt.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Learning new things, experimenting

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? A little bit

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

How wanted was this hookup for your partner at the time? Not at all

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

To whom did you talk about the hookup? How did they react? Just with ourselves. Gary has never mentioned it to my knowledge.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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? A little bit

Why do you regret this hookup? Because it made Laura Ashleigh question herself and wonder if I thought she was “scandalous” or a “slut.”

What was the BEST thing about this hookup? Watching L.A. let go and release her inner freak.

What was the WORST thing about this hookup? The insecurity that followed.

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

All things considered, how NEGATIVE was this experience? Somewhat 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? It’s okay to explore.

What do you think about the Casual Sex Project? Love it.

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