Pregnant Friend



What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business Owner Property Management and Leasing
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? None
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 1

Pregnant Friend

How long ago did this hookup happen? Yesterday Dec 14th

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

How would you best classify this hookup? Friends-with-benefits

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? Maddie is 31, married, with a son age 5 and just got pregnant. I have known her and her husband for 7 years now. She is 5’5″ and has blonde hair, blue eyes, a button nose, beautiful full lips, not large, not small, just right boobs. Her upper body is long, with shorter length legs. I have been personally attracted to Maddie for over 4 years now, but since we both are married never acted on it. We have deep, engaging and insightful talks, are both impulsive and don’t like to plan what we do. We both have teased out our naturally feelings for each other, and at different times have told the other of our abiding attraction and deep caring for each other.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Maddie has a salon parlor in her house to cut hair, and my wife and I had met there to get our hair cut. My wife went first and then our adult son, and then I went. My wife and son left for appointments after their haircuts, leaving Maddie and me alone there. As usual, we had a good ten minutes of small talk that led to a deep conversation about whether people really care about other people. As Maddie finished the haircut, I then stood, taking out my wallet and she looked at me and getting extremely serious told me, her eyes holding mine with her sincere gaze, “I want you to know I really, REALLY care about you Drew.” “How much I asked?” “I love you” was her reply. By now I had taken the cash out of my wallet to pay for the cuts and give her an annual Christmas bonus, and I tucked the money into my waistband above the button on the top of my pants.

Maddie smiled and said “What do I do with that?” “Well, if you want it, take it” I replied. Maddie came over to me, standing next to me and lifted the money out and placed it on her counter and said “Like this?” and she kissed me, passionately, deeply, her tongue entering my mouth, our tongues then twirling, intermingling as we french kissed.

For several minutes we just kept kissing and I felt her hand brushed my hardening penis, and Maddie took me by the hand. Her son was in school and her husband at work and so Maddie led me through the door, into the hallway, and to her master bedroom.

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 we entered the master bedroom, we stopped and both said at about the same time “You sure?” then we giggled. Maddie with her bold and beautiful blue eyes looked at me saying, “I’ve wanted you for so long Drew. Yes, make love to me right now.” I had wanted this woman for a LONG time as well so that was all I needed. I kissed her again, lifting off her shirt and undid her black bra and her pants. In two motions, I then removed her jeans and her underwear.

Her breasts were slightly enlarged and her nipples were rock hard. I love breasts so I reached out, touching them, massaging them and massaging mainly the outer sides as Maddie moaned slightly when I touched her there. Maddie lifted off my shirt, my tee shirt and then undid my pants and removed them. I took off my socks. My penis was hard, and hardening and as she kissed me, her fingers touched my dick, exciting it even more. I led her, kissing and touching to the bed where we laid down.

On the bed, we made out for another ten minutes, me touching, massaging her breasts and playing with her nipples, making them harden with excitement. Maddie played with my balls and my dick, hardening my dick to its full size. I took my hand down and felt her inner right thigh and worked my way up to her vagina. Maddie was soaked, so now I went from kissing her, to dropping down and kissing her neck, the back of her neck really turned her on, and then kissing and sucking her breasts and then her navel. I went down and kissed her inner thigh just above the knee and watched her smile as she spread her legs.

I now kissed up to that wonderful inner thigh and arrived at her vagina area. Using my tongue and my lips I kissed and licked her pussy lips, going up the right side, down the left, back up the left and down the right. For the next ten minutes, I did this, inserting my tongue like a hard tiny dick into her vagina causing her to moan as I tongue fucked her. Now slowly, I worked my way up to Maddie’s clit and experimenting and judging her reaction I found that her right side, between 10 o’clock and 1 o’clock on her clit was her sensitive and arousal area. Now I worked that area, applying just a hint of pressure on it and increasing it over time. Slowly Maddie responded and started rubbing her clit on my harden tongue and then really rubbing it and then going for it until she screamed and I felt her shoot a stream of cum onto my chest area.

With her screaming, I moved into position and Maddie lifted her leg and we began to spoon fuck. I felt the head of my penis rub her vaginal area, and then rub her vagina. I rubbed her a good ten to twelve times and finally, Maddie drove my dick deep inside of her vagina.

Damn, it felt so great to feel her wetness, to feel her hunger, to feel her love and desire. As I filled her vagina completely, she kissed me and said: “I love you.” I replied “I love you too” and kissed her and began to move back and forth in her. I withdrew about 1/2 way out and then would drive my dick deep back inside of her. Maddie matched my pace rocking back and forth with me moaning “So good” I asked, “What is good.” Maddie replied: “You,” “you in me,” your dick on my spot.” Consistently we maintained the same pace and if I tried to slow down, Maddie made me return to that same pace. “Don’t stop, GO!” was her reply.

So I kept it up. I could see in her face as her neck and cheeks turned rosy she was close to her orgasm. Maddie increased the pace of our lovemaking and I could now feel my cum enter my penis, making it swell larger and thicker. “Oh hell yeah!” and lots of “Oh, Oh, Oh, Yeah, Yeah, Yeah” as Maddie’s pace went to a frantic level, my penis now going all the way inside of her and about 3/4 of the way out. Suddenly I could feel her vagina quiver, and then her body as she screamed out over and over “YES, YES, YES, OH, YES, OH OH YES!”

Maddie now drove my dick completely in her, and squeezing my dick I ejaculated inside of her. I moaned in pleasure as I shot my cum and sperm deep inside of her over and over again. I felt her vaginal muscles squeezing my dick to get every ounce of my cum out of it. We made out, kissing and as we kissed, I looked into her eyes and said “I really love you” She smiled and said, “Me too.”

We left my dick in her as I still oozed out some of my cum inside of her, and we kissed and talked. We decided not to tell anyone of this moment and as I finally withdrew, we kept talking and kissing. I asked about protection, to which Maddie said, “I want none. I prefer my mean raw.” with a wink. She began to play with my balls and dick again and I her breasts and neck.

Soon, we were ready and we made love again, for the second time. This time Maddie rode me, being on top and we made love for a good forty minutes. We varied the pace, sometimes speedy up, sometimes slowing down, sometimes be consistent. Maddie’s boobs were enlarged and her nipples rock hard. Anytime she leaned forward on me, I would kiss and sucked her nipples. When she was on top and sitting straight up, I rubbed her boobs. We’d hold hands during this position, interlocked our fingers. Other times I ran my fingers up and down her thigh turning her on.

At one point she leaned forward, I sucked her boobs as she began to super thrust my harden penis in and out of her vagina. I could tell now I was close, my dick enlarged and became swollen as my cum entered it, and Maddie felt it also. “Yeah, I like that” and she thrust faster and faster until I felt and heard her having her multiple orgasms and I moaned in pleasure as my dick, unable to hold it any longer, shot my wad, my cum, my sperm deep inside Maddie as she exploded in wave after wave of orgasmic pleasure.

She fell on top of me, lifting and spreading her legs so I could drive deep inside of her which I did. Maddie kissed me and began again to squeeze my dick, milking out of it all my cum and sperm. I stayed inside of her again, and we talked. We found out that neither one of us at this time wanted to leave our spouses, but we had to admit our attraction to each other. I asked Maddie: “Okay, one time hook up or an affair?” “Affair, when we can” was her reply.

As I withdrew my penis from her, I moved to get out of the bed. Maddie grabbed me, hugging me said: “No, once more.” She then kissed me again, over and over so I couldn’t reply. This time she got out some KY from the headboard, a new tube as she said her and her husband never had a need for it but she knew we would, and she wetted herself with it, and then put some in the palm of her hand, she used it to begin to jerk me off.

Since we had talked and stuff for thirty minutes and another ten minutes had gone by, I responded to Maddie jerking off my dick. I got hard, and I used my finger on her vagina, inserting it and finding her g-spot stimulated that. Maddie moaned again as I played with her and if she had kept up stoking me, I would have come. Instead, Maddie pulled me on top of her, spread her legs and in the missionary position, guided my now hard dick with her hand, inside of her vagina.

I love how her vagina fits my penis. Perfectly is the best description. I stimulate her deep spots. Her wetness and juices drive me nuts as I dick enters her. No different now. I entered her and kissed her and began a consistent in and mostly out motion with Maddie for the next ten minutes. After about seven minutes I knew Maddie was close again with her breasts enlarging, her tits getting supper erected and she wrapped her legs around me and squeezed my body and my dick.

This time I paced it perfectly. Exactly as her body and her moans told me she was having her orgasm, I shot my cum off inside of her vagina, sending her to scream. I drove my dick deep and completely inside of her each time I shot off a load of cum into her. Her legs squeezed me hard, her hand felt to the side of us and on the bed. As the screaming subsided, Maddie moaned.

We stayed with each other for a good twenty minutes after making love for the third time, holding, kissing and talking. Eventually, we got up and took a shower. After I had washed my dick, Maddie went down on me and gave me a damn good blow job. She wasn’t about driving my dick completely into her throat like I was making love to her mouth. Instead, she used her tongue, her magical tongue and licked the tip top of the upper penis head. She rotated doing that and just putting the head of my dick inside of her mouth. That lasted for ten minutes in the shower and as she felt my dick swell and pulse as my cum entered it she increased the motion. And as I felt my penis swell one last time, she put about two half of it in her mouth and I erupted into pure pleasure. I mean, I shot off another 4 or 5 ejaculates into her mouth as she smiled and swallowed all of it. Damn, that was incredible!

We then dressed, kissed goodbye and arranged a time for next Wednesday.

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?

We talked on the phone this morning. I told her I thought of nothing else but making love to her yesterday and the funny thing is, that is what she is thinking about. No one is home until after 7:00 pm at my house today, and I am off work so Maddie has invited herself over for some wonderful afternoon delight. She just texted as I entered this that she is on her way. So, for now, our plan to make love with each other is going to continue and we have no expectation outside we know we want to be lovers moving forward for a long time. Neither spouse for us is that active sexually, both marriages are almost a sexless marriage.

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)

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, just each other.

How would you best summarize people’s reactions to 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? First, the sex is the best I have ever had. Why? Because I am deeply attracted to Maddie and enjoy her. I think sex is always better if you know the person and feel something for them. The most important is that we both crossed over the line, admitting our emotional caring for each other, our physical/sexual attraction to each other and that we can do this and still retain our marriages.

What was the WORST thing about this hookup? Having to stop. I just wanted to make love all night long.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No. I thought I was monogamous and I am, both to my wife and to Maddie. I am not going about or around screwing someone just to screw them. I need a connection. However, it has made it easier to see that having a friend with benefits helps to improve my marriage as I know now I am not going to push my wife for having sex with me.

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? Great experience and it is on-going.

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 said them above.

What do you think about the Casual Sex Project? Interesting

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