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What’s your gender? Man
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? US
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Retail manager
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? Few

Helping Out

How long ago did this hookup happen? About 3 years ago

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For more than 3 years

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? Kate (not her real name) was a girl I went to high school with. We were very good friends but never anything more than that. She was bi. We kept contact after high school mainly through texting and email until about 5 years ago when she needed a job and started working for me. As time went on, we caught up on old times, and I learned that she had a significant other, a girl. At the time, women couldn’t legally get married, but they finally are now.

As time went on, she opened up about the two of them being serious and wanting to have a kid together. Unfortunately, they were stuck in a hard place because they could not afford artificial options and neither of them had anyone that they trusted enough to be a direct donor. Through a couple of weeks, that topic kept coming up until finally she came right out and asked if I’d be interested in helping. She said that she trusted me and wanted me to meet her girlfriend to see how she felt about the idea. I agreed and we decided to meet for dinner one night at their apartment.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I met Kate and Ashley (again not a real name) for dinner. It was apparent Kate had told Ashley about our history as friends because Ashley treated me as if she’d known me for years. We sparked an almost instant friendship. We had dinner, and soon after, we had the “conversation.”

About Kate and Ashley:
Kate – white, average body type, 32B, brown hair and eyes, cute butt.
Ashley – white, also average body type, 34C, great ass and hips, blonde hair, blue eyes.

About a week after dinner, Kate told me that they wanted me to help them. She told me that Ashley was going to be the “mom” and wanted to make sure that I was okay with that. I gave her the reassurance that I would do whatever I could to help and that I had no intentions of anything outside of helping them with what they wanted. We made a plan for Ashley and I to have an evening together the next weekend.

About mid-week, Kate came to me and told me that there was a slight change in plans. She told me that since we were both off work the following weekend, we would postpone the rendezvous until then and that the 3 of us would go out of town for the entire weekend. I agreed but asked why the change. She just gave me a flirty laugh and said that she might want to have a little fun with Ashely and 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? As a token of good faith, I got us a hotel suite in a city a few hours away with a king-sized bed. As soon as we got checked in, we all went to a nice dinner before returning to the hotel. I waited in the living room area as they went into the bedroom to get ready. When the door to the bedroom opened, they came out together both wearing matching bra/panty sets, black lace bras with lacey black thongs. My cock got instantly hard, which they could easily see by the bulge in my khakis. They kissed each other and Kate said, I think he’s ready for us. They came over to the couch, stripped me naked, and began a rigorous tag-team blowjob. I warned them to take it easy because I hadn’t cum in nearly two weeks, saving it all up for the cause. They led me to the bedroom where I waited in the corner, slowly stroking my cock and watching them strip and make out with each other. After Kate brings Ashley to orgasm through some oral and fingering, she motions me to come over and join them. Kate guides me into Ashley’s extremely tight but dripping wet pussy. Ashely gasps as I enter her and tells me to be gentle as it has been a while. I make slow, deep strokes as Kate starts kissing me with lots of tongue. Once Ashley starts moaning with comfort and pleasure, Kate turns her attention to Ashley, sucking her tits, kissing her, etc. I try to hold back, but she’s too tight and I start feeling that my balls are going to explode. Kate can tell by my expression how hard I’m trying to hold back and tells me that we have the whole weekend for fun so go ahead and do what I need to do. So I grab Ashley’s legs and drape them up across my shoulders. The first stroke in that position makes her gasp again and sends her into an orgasm. As her pussy clinches my cock, I start pumping her harder and faster. As she catches her breath, she begs me to cum for her. I pick up the pace a bit more and flood her pussy with two weeks worth of hot cum. It felt like I was shooting into her for like 2 minutes before it stopped. As I pulled out, Kate took my place and began licking Ashely’s pussy. I was still rock hard and staring at Kate’s ass when she looked back at me and says, “It looks like you’ve still got some left for me.” I took that as my invitation and plunged my cock inside Kate from behind. She too was extremely tight and wet. Her moans were muffled in Ashley’s messy pussy but I could still hear them. I grabbed her hips and pounded her hard and fast. I warned her that I was about to cum and she stopped licking Ashley long enough to encourage me to fill her pussy up too. With one last deep thrust, I pumped Kate full of cum also. After that, we all collapsed on the bed together. We laid there naked and chatting for a while. I learned that I was the first cock that either of them has had in nearly six years and that I was the only guy that has ever cum inside of Ashley without a condom on. We chatted and chilled for a bit longer before getting back into another heated session. This time I was nailing Ashley from behind while she licked my cum out of Kate.

We spent the whole weekend having raunchy threesomes with me pumping cum into both of them repeatedly. Occasionally I’d just enjoy watching the two of them go at it for a while before I joined also. By the time I got back home from the trip, I had cum so much that my balls were sore.

Next day at work, Kate and I acted normal as if nothing had ever happened until she whispered to me that we should probably keep trying until we find out that it has worked and told me to come to their house on Wednesday night.

We all hooked up frequently for the next months. Sometimes threesomes, sometimes just me and Ashley while Kate was at work, sometimes just Kate and me either when Ashely was working, or right after work in my SUV before we left. One night, Kate sends me a picture message of a positive pregnancy test, followed by a message that it wasn’t Ashely that was pregnant though. We had a celebration dinner that following weekend. They told me that since Kate’s hormones would be raging, we should continue our “relationship” until the baby is born and that Ashley was going to go on birth control so that she wouldn’t get pregnant also.

We continued as planned with threesomes and one-on-ones until the baby was born. Since then, I have regular contact with them (Kate still works for me) and the baby. I am referred to as his uncle, which I have no problem being. On occasion, we all still hookup though nowhere near as frequently.

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 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), Emotional intimacy, closeness, connection

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? I told my best friend about the hookup/relationship situation just not who it was with.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Unprotected sex with two hot women, one of whom I had secretly been wanting to have sex with since high school

What was the WORST thing about this hookup? Having a kid that only gets to know me as uncle instead of dad.

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