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What’s your gender? Woman
How old are you? 34
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? NYC
Highest education received: Some college (currently in college)
What’s your occupation? Advertising
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Kinky
How many sexual partners have you had in your life (including oral sex)? 20-30
How many hookup stories have you here posted before? O

Addicted To Double Penetration

How long ago did this hookup happen? 4 years ago

What was your relationship status at the time? Same as current status

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 hubby and a complete stranger. My husband David is 14 years older than me, in good physical shape, Caucasian and is thick and above average downstairs. The stranger was about my age, with a semi-muscular medium build, he was not as thick as my husband but about the same length downstairs.
We decided to have a threesome and used the internet to find a “stunt cock” to have fun with.
Before we met I was nervous and excited all at the same time. I was afraid I would be too self-conscious or too stuck in my head to go through with it.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? This is sort of a long story. It began in my early to mid-twenties when I first began watching porn. After seeing a double penetration for the first time I was obsessed with it! Almost every time I touched myself I would fantasize about being the center of attention with two guys who would their way with me.
I was married before David and my ex was super vanilla, jealous, and felt threatened by anything even slightly kinky. I remember him being weirded out when I suggested us buying a vibrator. Needless to say when I remarried I kept my fantasies a secret, that is until I found an open porn clip on David’s phone! And what did I see? My favorite porn star getting a DP! So that night I suggested that we watch porn together. I had assumed that like pretty much every guy I was with up until then: he was into girl on girl, or a guy and two girls, so I suggested we watch that. After a few minutes, he asked: “How do you feel about two guys with a girl?” I said, “How do you feel about it?” He said, “Sometimes I fantasize about sharing you with another guy!”
I couldn’t believe what I was hearing!
After that night my sex life changed forever. During the following months, I began climbing out of my sexually repressed shell. David and I got honest with each other and began sharing our fantasies including the deepest darkest details. I began truthfully telling him what I fantasized about when I touched myself. He was never judgemental and actually encouraged me to touch myself when he was at work. This in itself was a super liberating experience and it built an incredible feeling of trust between us.
If I’m honest here, up until this point sex was something that I used as a tool to get what I wanted in my relationships. If I wanted my partners to buy me nice things or do yard or housework I would withhold sex or blow jobs to get what I wanted and would fantasize and masturbate when they weren’t at home. Typically I would only have sex two to four times a month. All of this was about to completely change! If I only knew then what I know now. Sigh.
David and I picked out and bought an assortment of sex toys: a magic wand, three realistic strap-on dildos, a strap-on harness, butt plugs and different lubes. Watching DP porn and experimenting together and alone became a thing.
We pushed each other’s boundaries. When alone I began inserting things in my ass and getting used to the sensation, which up until now had felt more non-sexual like pooping than anything pleasurable. I started with a medium size lavender colored silicone plug. It took lots of lube and time to fully insert into my tight ass, but once inside I loved the feeling of fullness, especially with the small dildo we bought in my pussy and the wand on my clit! Orgasms felt different, fuller, harder and more satisfying. After a few months, I began sliding the small dildo in and out of my ass, focusing on the warmness and full feeling which I was began to crave after climaxing with only the wand on my pussy and the dildo deep in my ass. I began DPing myself with two dildos and watching my lady parts stretch over them in the mirror. I absolutely loved the sensation of having two toys pumping in and out of my pussy and ass at the same time. Because our dildos were designed for strap-on use they are all wider, flaring at their bases, so I struggled to hold them both and use the wand all at the same time! I finally got the courage to ask my husband to DP me with the strap-on! The night it happened we did it doggy with his cock in my pussy and the small dildo in my ass. We used lots of lube and it took a while for him to fully penetrate me. He lightly caressed my back and hips while this was happening but once he was fully inside he pushed me forward and fucked both of my holes hard and fast. I came super hard and for what felt like ten minutes as I pressed the wand against me.
Over the next four or five months, we experimented with different positions and the larger dildos. One of them is unnaturally huge! At first, I didn’t want it anywhere near me, but after playing with it, and cumming on it during my alone time I came to love the thing (which we fondly nicknamed “The Big Pink” because it’s flesh pink and even has bluish veins!!). Having an orgasm on David’s cock in my ass with Big Pink deep in my pussy completely is an almost indescribable feeling. I have since helped my husband DP other women by wearing “TBP”, but that’s a whole other story!!
David and I fantasized and experimented together for roughly a year. I noticed several things changing: our sexual activity dramatically increased, (we used to do it a few times a month now we’d do it 3-4 times a week), and I touch myself way more than before. But what I noticed the most was that we began communicating more, not only about sexual stuff but about our feelings in general, we were becoming closer than ever before. After we got married and had our daughter our sex life depleted, and we fought and bickered more than we actually shared our feelings. It’s as if we had retreated into two separate worlds: I was a mommy and he was the provider. I don’t know what exactly triggered the changes but we elevated our trust level and we’re seeing each other honestly for what we are. When the sex increased and got kinkier my husband was home a whole lot more often, and listen up ladies: he began helping with housework! He actually vacuumed! Besides that, he began taking me out more and in general was much more open. It is amazing and was definitely awakening for both of us!
After about a year and a half later we began talking about the possibility of acting out our fantasies. I think we were both nervous but wanted to try it at least once. We figured it would either be good or bad, and we would act together in whatever we did.
From there we talked about what we wanted and expected from each other and set boundaries. We also talked about how to go about finding a guy or couple to hookup with. I suggested going to a swinger club, which didn’t work out so well. Long story short the place was nice, had a bar, sex rooms, etc. but we didn’t see any attractive people that we wanted to have sex with, and when we started to kiss in a room with other people doing it, a couple in their 60’s came over and asked if they could join us, and for me it killed it and we left.
After that, we posted on a threesome sight and we began talking to guys and couples. This was hot in itself. We decided that while on vacation my husband would go interview the guy I picked without me, and he would be on call while we were hooking up. If I texted “I’m ready” he was to come up to our hotel room, get undressed and join in, he was not to kiss me unless I instigated it first and was to leave shortly afterward. If I didn’t text it was a no go.
So after endless emails, we had landed in San Francisco for vacation and arranged for a hot stranger to meet my hubby at the hotel bar.

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 interviewing our potential partner my husband returned to our room. I had just showered, was freshly shaved and put on fishnet stockings, garter belt, and garters, and that was it.
When he walked in the room I asked: “How did it go?” He didn’t answer, he just walked over and began kissing me. I could see by the lump in his jeans that he was excited. He picked up my phone, entered a phone number on the text screen and typed “I’m ready” but didn’t hit send. He just handed it back to me and returned to kissing and touching me. The next thing I remember is the feeling of his cock rubbing in circles on my clit and the outside of my pussy. I wanted him inside of me, but he kept teasing until I was begging him to fuck me.
As he began sliding it in he looked me in the eyes and asked: “Do you want to be treated like a princess or a whore?” I didn’t answer right away, and he pulled out and returned to sliding the head of his cock in circles on and around my clit, then almost unexpectedly the words “a whore” escaped my mouth. Before I knew it he had my knees pushed back against the mattress and was pounding his thick cock in and out of me with relentless force.
He asked “are you ready to be the little slut I know you really are?”, I said yes. He responded “do you want to get fucked by two cocks at the same time?”, I said yes! Then without stopping he handed me my phone, and just after I hit send I closed my eyes had a huge orgasm on my husband.
When the stranger walked in he didn’t say anything, He just walked into the bathroom and came into our hotel bedroom totally nude.
David was still fucking me from behind gripping my hips and thrusting. The stranger walked over and I reached up with my left hand cupped and massaged his balls while my right hand and mouth wrapped around his semi-hard dick.
A few seconds later as I felt him get rock hard I realized that I had a cock in my mouth and one in my pussy, and with just this thought another orgasm began building. It hit with lightning force! I felt my back arching and came with big cocks sliding in and out. I felt dirty, hot, sexy, desired and free. I looked up and could see in the stranger’s eyes that he wanted to fuck me, I continued to make eye contact and began sucking harder and faster. I was completely living in the moment and wanted to please and be pleased.
I felt my husband drip some lube on my ass and felt the head of a dildo beginning to push against it. I could feel it stretching my ass open and entering me. I felt amazing! After several minutes, he asked, “are you ready to get fucked by both of us?” “Yes,” I moaned. David had the stranger lay on his back on the bed with one foot on the floor. He guided me over and on top of him with my back facing away from him. I slid his cock into my pussy and began riding him. My husband had his hand on the dildo that was still deep in my ass. He slid it in and out, we made out while I rode the stranger. He asked “are you ready” I nodded yes. He lifted me upwards and slowly slid out dildo out and the stranger guided his cock into my asshole. I slid onto it and laid back against the stranger’s chest. David leaned forward and entered me, and OMG it felt amazing! The sensation of two cocks pumping me at slightly different rhythms, two men breathing, groaning, and talking dirty was unlike anything I could’ve imagined. I groaned and came uncontrollably! I was in heaven.
The stranger came fairly fast deep in my ass. I could feel him convulse inside of me. He was wearing a condom which made it less messy. David didn’t stop fucking me for another ten or fifteen minutes. The stranger was inside of me for the duration, and although he wasn’t fully erect the feeling of fullness was still incredible. I think I came twice more before David pulled out and came all over my chest.
After that, the stranger retreated to the bathroom, got dressed, said goodbye and left.
David and I snuggled and about an hour later we made slow passionate love. He told me that I was beautiful.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? The next day I was sore! We went out for breakfast at a hipster restaurant full of hungover 20 somethings. I felt secretly devilish and sexy. I thought about all of the bad sex they must be having, looked and David and felt really in love with him. We were both glowing.
The weirdness we were both afraid of didn’t exist. I think because of the fact that we talked about everything multiple times before any of it went down and the fact that David made sure that I was ok with everything first and foremost. That made me feel safe. Also because we kept a connection the whole time.
We have threesomes two to four times a year, we make them special occasions and always play out of town with strangers. We always practice safe sex and David usually suggests it but always leaves it up to me. We play with both men and women and alternate equally.

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

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

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

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

What substances did your partner(s) consume? Marijuana, hashish

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? Our secret.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Being encouraged by my partner. Being sexually free, and getting to act on something I’ve fantasized about for years.
Becoming closer to my husband as a result.

What was the WORST thing about this hookup? Emailing multiple people, dealing with gross dudes, until finding a good fit.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Absolutely!

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

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

Anything else you want to add about this hookup? It made me realize just how sexually repressed I was before.

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 would like to see the slut-shaming culture disappear. I’m not suggesting a ton of casual sex, cheating or anything like that. I’m saying be honest with your partner, and don’t be ashamed of your desires. Experimenting is ok and encouraged for both of you.

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

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