To Boldly Go Where I Never Went Before



What’s your gender? Man
How old are you? 53
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: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Professor
What’s your current relationship status? Engaged/Married (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)? 14
How many hookup stories have you here posted before? 1

To Boldly Go Where I Never Went Before

How long ago did this hookup happen? Last Week

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? M is 18 years younger than me, has two kids and has been married for 10 years. Well, she is pregnant with her second. She has blonde hair that is down past her shoulders with hazel green eyes and she is about 5’6″ tall. Intelligent and witty, M enjoys laughing, sharing and talking. She is one of my wife’s best friends and I fell totally in lust with her about 5 years ago, and then we found…well, you’ll see if we found anything.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? M is pregnant and she and her husband are moving. I was off for a break since I am not teaching classes this semester, only attending to my graduate students. Since I was home, and M’s husband wasn’t, my wife volunteered me to help M unpack at her new house. I spent two days helping M unpack and organize, during which time we talked. Toward the end of the second day, M’s father picked up her 5-year-old son to go have Grandpa time and that left M and me alone. We talked casually and then M got on to the subject of her sister, whose husband was kicked out for having multiple affairs with other women. M asked me what I thought about that and I was honest. I have been married for 28 years and have had great times and more difficult ones. My wife currently refuses to engage in any sexual contact due to health issues, and it has been that way for 6 years. Sex is just too painful for her. M knows I have been faithful to my wife, but I finally opened up today and told her my real feelings.

I shared that I deeply missed being kissed, hugged, undressed, touched, and making love with a woman I know loves me. I told her, as she knew, that I wasn’t into just screwing anyone anytime, but I was to the point that if a woman I deeply cared about made a move on me, I would give in IF that woman committed to a long-term affair. M said that was different and her sister hadn’t quit having sex but had never agreed for her husband to dabble in sex with other women.
Then M asked me, “so who would you sleep with or who would interest you?” I wasn’t about to tell her that I had had a crush on her for years and that in truth, it was her so I brushed it off with “It doesn’t matter, she’s married with kids and has told me she would never cheat.” “You’ve asked her, haven’t you?” M replied. “No, not directly.” At that point M came over to me, leaving the kitchen and the unpacking of the last box for that kitchen, and came to where I was standing and leaning against the island in the kitchen.
“Suppose I told you I love you?” M said. I knew M cared deeply about me, she had told me that before. “I know that,” I replied. “No, I am in love with you and have been for years.” M countered. She then laid her two beautiful hands and fingers on my chest, and rubbed my shirt a couple of times and then drew her arms around the back of my neck and drew me down to her. Our lips brushed gently against each other’ and we kept our eyes open, looking at each other. I saw that emotion-filled, I love you look that I had been missing for all these years and knew my eyes betrayed me. M smiled and asked “Dave, do you love me? Do you want me?”
I can’t lie, I am a horrible liar and so all I said is “I am so in love with you” and I kissed her. I kissed her firmly, pressing her body against mine and holding her tight. My tongue now came to her lips which she opened, and we began to make out. I ran my hands over her butt, squeezing it and then up her back and to her breasts, gently squeezing them with my hands. M undid my zipper and then my button at the top of my pants and my belt, and guided her hand down my boxers to my hardening penis. Smiling, M stopped kissing and touching, and taking me by the hand, she led me to the 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, the bed was made and this room had been unpacked completely. M french-kissed me again, sending her right hand down inside of my boxers and stroking my penis. I undid her blouse and removed her bra revealing her large breasts with her huge nipples. Her nipples were erect and I knew I had to have them in my mouth. M now removed my pants and socks leaving me naked from the waist down. M was naked from the waist up so we slowly removed each other’s clothes. I kissed her and said “I need more than one time. I will need an affair.” M replied “Shut up and make love to me. I’m yours today and for a very, very long time.” We kissed and I led her to the bed, where we laid down side by side.

I parted her legs and began to rub her vagina. M moaned “Oh yeah” and began to stroke me faster. I was extremely hard by now and ready to cum. I inserted my finger after exploring M’s vaginal area, rubbing it, using my index finger to explore the folds surrounding her vagina and stimulating her clit. For the next several minutes, I increased the speed and hardness of my finger, alternating between my middle finger and my index and middle finger to screw M. M began to move her butt around and to gently lift it up and she moaned in pleasure. I went faster and she joined my motion, matching it until she erupted into ecstasy and screamed out multiple times in pure pleasure. It felt damn good to pleasure a woman I love again.

I moved my mouth off of her neck and began to suck her nipples and breasts. M held me tight and then gave me a gentle push down. I got the message and moved from her breasts, down her tummy and then down her pussy hair to her inner leg and using my tongue. I licked her vaginal folds and her clit, moving her back toward pleasure and orgasm. I hardened my tongue and after licking her vagina I drove my tongue inside of her. She moaned and I licked her vagina and her g-spot until she erupted into multiple orgasms. She now pulled me up to her and we began to make out again. I was still hard, but not as hard as I had been. M smiled and then kissed down my neck, taking her time, down my chest, then kissed down my stomach to my penis which was quickly hardening. M now used her right hand to hold the base of my penis, squeezing it tightly and then she used the tip of her tongue to lick all around the head of my penis. She found that I was most sensitive on the back of my penis head, and she worked those areas with that wonderful tongue and my penis swelled. Finally, she inserted my penis into her mouth and having been so long, I instantly wanted to blow, but couldn’t, her hand was stopping me. She now used her mouth to screw my penis and after a couple of minutes, she let go of the base of my penis which filled with cum, and I exploded into her mouth. M swallowed and drove my ejaculating penis deep into her upper throat sucking and milking it so I kept cumming.

Afterward, we laid side by side, smiling, kissing fingers, rubbing and she began to stroke me. “I want you inside of me,” M said smiling. My fingers ran all over her vagina while we both used KY to stimulate each other. We took our time, enjoying each other, kissing and staring into each other’s eyes as we touched, explored, enjoyed and connected. I have to admit, at this point my deep caring and love for M as a person and as a woman had gone from that to an intense desire, love, and emotion for her. I said “I love you” to her and she got emotional. I kept touching, kissing and holding and she said “My husband just thinks I am an object, something he owns. I have wanted to feel loved for so long!”

With that, I kissed her, deeply, with all the emotion I could muster. I felt my penis now stiffen and my fingers told me M was soaked again, ready to make love. I rolled onto my back, and then moved her on top of me. As she sat on top of me, M guided my penis to her opening. She looked at me and simply said “I love you” as she drove her vagina down on top of my penis. M was controlling speed, depth and everything. She was holding my hands, our fingers interlocked and when my penis head entered her, she squeezed my fingers. M now drove the full length of my penis shaft inside of her vagina, and she sighed as my penis completely filled her. Slowly, M pulled my penis out of her and then enjoyed having it fully enter and fill her over and over.

I thought ‘no condom’ but then again, neither one of us has slept with our spouses for a while and not with anyone else, and M is pregnant, so no biggie. I decided not to ask about a condom but to enjoy the ride, natural. I unlocked my hands and began to massage the outer edge of M’s two breasts. She moaned and smiled. Soon I felt my penis swell, I knew my second round of cum was entering and so did M. Her eyes grew wide and she went faster. I grabbed her hips and helped her thrust my penis deep inside of her, causing her to moan.

M screamed and said, “Cum in me, Cum in me now!” My penis remained deep in her vagina and she used her kegel muscles to squeeze my penis. I thrust deeper into her vagina as she moaned in pleasure and suddenly I shot my entire load of cum deep inside her. “I want it all, I want you Dave.” We began to kiss again now, as I kept ejaculating deep inside her vagina and she moaned quietly now, her orgasms and climax taking over her body. After this M laid on my chest and she said: “I wish this was your baby.” I smiled and said, “perhaps in time.”

With that, we fell asleep and woke up 2 hours later, made love one last time with plenty of foreplay as before and then I had to go home. My wife noted I was gone for a long time and I told her M needed help finishing up in the kitchen and in the bedroom.

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? M and I have talked and made love twice more for about 6 hours each time (multiple love making each time). We are in love with each other and don’t want to ruin our families but don’t want to be without each other. For now, we are going to be lovers, partners in making love and doing things that allow us to continue to strengthen our love. Some of that is definitely sex a couple of times a week, some is just hanging out together. Her baby will set some of that back, but she is adamant it won’t set back the sex. We’ll see on that.

The bottom line is we are long terms lovers and are content with that for now.

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, Hoping or expecting it would lead to something more, To feel loved, cared for, to

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.

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? I connected with a woman again, one I had feelings for and strengthened our love for each other. It felt so GREAT to be touched, caressed, kissed, and made love to.

What was the WORST thing about this hookup? That we are not at a point where we can be totally open about this. My wife would be okay with it as she told me M is someone she would let me sleep with if I wanted to and M agreed. M’s husband has no clue though and we’ll see how that plays out.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yep. If your in a sexless relationship don’t put up with it. I found I don’t have to put up with that and I don’t have to go screw everyone that comes into my life. I can find one person that I care about and if we both agree, find the sexual fulfillment, the emotional fulfillment we both need in each other and not be guilty about it.

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? I forgot how great it is to make love to a pregnant woman! It is incredible! Don’t mind that it isn’t my baby (wouldn’t be as I am fixed) but it was wonderful to be with M.

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? Best times are when I am sexually active in a relationship. It heightens, binds and fulfills.

What do you think about the Casual Sex Project? Interesting

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