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What’s your gender? Man
How old are you? 52
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? Small Business Owner
What’s your current relationship status? Married; thought it was 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? Bored
How many sexual partners have you had in your life (including oral sex)? 9
How many hookup stories have you here posted before? 2

Second for Wife, First for Me

How long ago did this hookup happen? Last Thursday

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

How would you best classify this hookup? Beginning of Long Term Affairs for Sexual Gratification

How long did you know the person before this hookup? For 1 to 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? This will be complicated as there are four of us involved. Originally there is my wife Lynn. Lynn is 5’7″ tall, with short black hair and she is 49. She has a 40D bra, her breasts are full, round and her nipples large. Lynn is not fat but is curvy, think Scarlett J. Lynn has a long body and shorter legs that will perfectly wrap around you during sex. She was very sexually active before our marriage, as I was.

We’ve been married for 28 years and she had a 4-year affair about 10 years ago with a co-worker that I didn’t learn about until after it was over. We worked through it with the main reason that she felt bored and wanted to explore. That turned into enjoying the sex with her co-worker a LOT and so she kept the sex up once or twice a week with him. His name was Matt and he was 8 years young than my wife, 6’4″ and he did indeed have a very long, thick penis, Lynn said it was about 8 to 9 inches long and a good 6 inches thick (they filmed themselves several times and that is how I caught the affair, I found her video on the computer). Matt was tall and very thin. Our sex life during that time remained active and outstanding, my wife just likes variety. She was getting it three to five times a week and said from two different men (me and Matt) she just loved it. Her point is that neither man was better, each was unique and fulfilled her differently thus why she loved making love to both of us. Eventually, Matt fell in love with her and my wife cared for him, but wouldn’t leave me or our kids so the affair was ended.

I am 6′ and 205lbs, with a slight middle-age belly though I do work out 5 days a week to keep it at bay. I have a full head of dark hair with some flakes of grey showing. I love sex, had a bunch of it before marriage and have remained monogamous during marriage to this point. My penis is 7 inches long and 7 inches thick, Lynn calls it thick and full.

Lynn has a new lover which I will share below. His name is also Matt and he is her boss. She is a controller for a large company and Matt is the CFO. They have known each other now for several years and have worked closely together with long hours. Matt is 6’2″, 42, married (in a boring and almost sexless marriage) has blonde hair and the blue eyes that go wit hit. He is about 215lbs, so not fat, but like me, forming a slight belly and he runs daily. As you’ll see, his penis is about 8 inches long and only about 5 inches around, so long and thin.

Becky is Lynn’s assistant controller, one of four, but Becky is young, 28, has had 1 major boyfriend in her life and he got her virginity before they broke up 3 years ago. She is 5’5″ tall, dirty blonde hair, full lips, long hair down past her shoulders, hazel eyes, and a size 36D bra with perfect breasts and nipples. Man, I love breasts and nipples. She weighs about 120 lbs, varying between 116 to 122. Becky has a tight ass and I have in the past often looked at her and thought she would be a good lay.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was at work and had just closed the books for January and we had had an outstanding month in my business. I decided to surprise my wife who had called and said she was going to have to work really late as the new payroll system they were bringing in was needing adjusting. So I thought I would bring her lunch, eat it with her and surprise. her. I stopped and got her favorite Mexican, and then drove the 40 minutes south on the freeway to her office. My wife works in one of three buildings the company she works for owns. She is on the second floor of the third building and her office and the CFO’s officer are together, with a conference room in between.

I arrived and got the food out and walked into the building. As I entered the accounting area, I began to walk down the stairs when Becky saw me and I saw a look of horror on her face. “Jason, how are you?” she inquired approaching me quickly from her office. “Great” was my reply. She then began to talk to me and after a few minutes, I began going up the stairs. Becky grabbed my arm and simply said, “Jason, you don’t want to walk in right now.” I knew from the look on her face it wasn’t because of some secret accounting meeting between controller and CFO. “Why?” I asked. Becky grabbed my hand now, and said, “Follow me.”

Becky led me upstairs and I noticed that the blinds to Matt’s office were closed and no one could look in. Becky led me to the conference room, and then shut and locked the door behind me. There was a table with chairs, a sofa, and nice lounge chair also, and a covered mirror. Becky said, “Are you sure you want to see?” “See what?” I asked. Becky now pulled off a covering on the mirror revealing a one-way mirror that let you see into the CFO’s office. “The last company installed it so when money counting which went on in the CFO’s office was done, other people could witness and watch to make sure it was on the up and up. We’ve never removed it.”

I now looked into the office, and saw Matt, massaging Lynn’s shoulders as she pretended to stare at her laptop screen.

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? Matt kept massaging Lynn’s shoulders and asked, “So how long of a meeting do we need today?” Lynn replied, “I called Jason and told him it would be 9:00 pm or 10:00 pm before I was home.” It was 12:30 pm right now. “I guess we have all afternoon and into the evening,” Lynn said smiling. Matt smiled as Lynn stood and said “Awesome.”

At this point, Lynn hugged Matt, and he returned the hug and their embrace brought them together. They looked at each other and then Lynn kissed him. Becky was still holding my hand and squeezed it tight which I barely noticed, my attention on Lynn and Matt. I could see their tongues eagerly exploring each others mouth and I watched now as Lynn unbuttoned Matt’s dress shirt, removing it and then his tee shirt, leaving his torso exposed. Matt now returned the favor, removing Lynn’s blouse and her shirt under he blouse. Next Matt removed Lynn’s bra, it joining the heap of clothes on the floor.

Lynn’s nipples were hard and erect. Matt began to kiss Lynn harder as his right hand now began to squeeze Lynn’s right breast. Lynn sighed, a sigh I had heard often in my life and it was one of pleasure. Lynn loved her breasts to be squeezed, played with and sucked. For the next couple of minutes, Lynn and Matt kept kissing and Matt kept rubbing, caressing Lynn’s breast, and taking a middle finger and index finger, squeezing her right nipple.

A part of me wanted to walk in there, but I knew the door was locked, and another part of me was sickly fascinated watching my wife engaged in foreplay prior to having sex with her lover. I then noticed that Becky was still holding my hand and had nuzzled into my right side. “Make me horny to watch them,” she said to me. I looked at her and could see her nipples were erect and I felt her left hand touch my balls through my dress pants. I let her undo my belt, undo my dress pants and zipper and felt my own relief as her young, soft hand began to gently play with my balls. We both kept watching as our own sex scene began to develop.

By now Lynn had matched Becky, had undid Matt’s pants and had removed them, and his socks, making him naked. His penis was hard, curved upward, and thin. Lynn began to use her fingernails on his balls, and then to stroke his penis, making it harder. After another five to ten minutes, Matt removed Lynn’s pants and underwear, making her naked. I could see Lynn’s tuff of pubic hair singling her love trail to her vagina. I now noticed that the sofa in Matt’s office was really a hide a bed and was pulled out and fully made. Lynn and Matt, hand in hand, walked to the bed now and made out again.

Lynn kissed Matt and then pushed him gently down onto the bed. Matt eagerly got on the bed and laid on his back in the middle. Lynn now got on the bed, moving to the middle and sitting on top of Matt. Her voice via the microphone speaker said, “Do you want me?” Matt looked at her and said, “More than you know.” With that Lynn leaned forward and down, and kissed Matt. As they were kissing I noticed that Lynn began to rub Matt’s curved thin penis up and down her vaginal area. Several times his penis came near her vaginal opening and she rubbed it up and down. Finally, using only her body, Lynn guided Matt’s penis inside of her vagina and moaned “Oh yeah, oh oh!”

Lynn began to now gently thrust Matt’s penis inside of her vagina and pulled it about halfway out before thrusting it out again. By now I was extremely hard. Becky was enjoying stroking me in rhythm to Lynn’s thrusting and Becky was smiling. “I’m going to make love to you today Jason,” Becky said with a big smile. “Only after they are done,” I said. “Fine with me.” I kissed Becky now, my tongue entering her mouth, her tongue wrapping around mine as we enjoyed our first kiss. I lifted off her shirt and undid her bra to reveal those beautiful, young and firm 36D breasts. Her nipples were hard as rocks and for the next five minutes I forgot about Lynn and sucked Becky’s breasts and nipples. Becky moaned “Oh, Oh, yeah, more, keep going.” I did and after five minutes I stopped and looked in on Lynn and Matt as Becky undressed me fully.

Lynn was still slowly making love to Matt. Matt’s eyes were rolling in his head as she squeezed her vagina on his penis. Lynn was a master at lovemaking and she was using her skill on him. Slowly she increased her pace, thrusting in and out, Matt now moaning “Yeah, oh, oh, oh, go, faster! Faster!” Lynn complied and began to thrust his penis into her faster and faster. I could tell Lynn was working hard to get an orgasm with Matt, but Matt had no problem Suddenly Matt moaned very loudly “Yeah, Yeah, Yeah, Yeah, Oh Yeah, Oh Yeah YES, YES, YES!!!” and I could tell he was ejaculating into my wife. Lynn kept up her pace now, going faster and faster, squeezing his penis, milking it and Matt moaning more. Suddenly Lynn screamed in pleasure, no words for it, she just screams in pleasure. She thrust seven more times and then fell on Matt’s chest, and began to kiss and make out again with him, both of them moaning.

By now Becky was naked and she had gone over and pulled out the hide-a-bed in the sofa in the conference room. Naked we stood there and I watched as Matt told Lynn in their afterglow “Damn, I love you.” Lynn replied, “I love us screwing too.” Matt replied, “I mean I love you, I think all this sex was having is making me fall for you.” Lynn sat up, and told Matt, “This is just about sex, and you lonely for it, me wanting variety, nothing more. Keep it to the sex and were good. Try to move it somewhere else, we’re done.” Matt looked at her and smiled saying “Okay, just the sex, right?” and he began to rub her breasts again. “Yep, just the sex,” Lynn said and she moved down his body, toward’s his feet and took his semi-soft penis into her right hand, holding it in the middle, squeezing it upward and licking the cum that came out with her tongue, and then licking the top of his penis hole and the top of his penis head.

For ten minutes Lynn worked on Matt’s penis, licking it, sucking it, inserting it into her mouth. Suddenly I felt a moist warmth on my penis and looking down saw Becky giving me a blow job. She was different as she just put my penis head in her mouth, and in her mouth licked my penis head all over. I moaned as my penis now grew rock hard, going to its seven to seven and a half inches and the full diameter of 7 inches. Slowly Becky started to insert my penis completely inside her mouth, so only the base of my penis was at her lips and my penis head was down the top of her throat. Back and forth she went, and man, I moaned softly a few times enjoying it.

I looked over and by now, Lynn and Matt had changed positions and Lynn was laying on her back on the bed, her legs spread and Matt was leaning over her. This was Lynn’s favorite position, missionary. I watched as Lynn drew Matt down toward her, saw that his penis had hardened firmly again from her blow job, and I saw Lynn grab his penis, and rub it along her vaginal area again. I knew she was rubbing her labia majora and then working her labia minora, or her pussy lips. That turned her on, A LOT and slowly she would use his penis head to rub her clitoris, stimulating it. Suddenly I knew she was at that point as Lynn lifted her butt into the air and squirted onto Matt’s body. That brought Lynn to taking the hard penis of Matt’s and thrusting it inside of her vagina. “Fuck me, fuck me hard and fast.” Lynn moaned. Matt complied now, thrusting his penis in and out of Lynn and Lynn matching his thrusts. Lynn now took over and rapidly she thrust Matt’s penis in and halfway out of her vagina, and in and halfway out, and in and halfway out again and again, faster and faster. I could see the pink glow come into Lynn’s breasts, her chest, her cheeks, and face. Suddenly Matt screamed out and thrust deep into Lynn as he ejaculated in her. Lynn screamed also, she loved having orgasms together in the missionary position with her lover and she wrapped her legs around Matt, squeezing him and thrusting his dick deep inside of her.

For the next two minutes, Lynn kept her legs wrapped around Matt, thrusting his dick deep inside her vagina, moaning, as she held him tight, his torso and her torso moving back and forth together. Slowly Lynn unwrapped her legs from around Matt, and keeping them bent at his side, kissed Matt long and passionately. Then she said “I do love fucking you. Your different then any man I have had. So don’t spoil it with talk of love. I want to be lovers for a long time. I told you four years was my last one, I want you that long also, but I will not leave my husband or my kids.” “But I make love to you better don’t I?” came Matt’s reply, wanting his ego stroked. “No. You’re different. Your long and thin in your dick and I haven’t had that. It stimulates different parts of my pussy. My husband’s dick is a good length but damn it is so round it makes me orgasm when it simply goes in me. Accept I use you both for different things and get use to the fact that I may just screw my husband tonight, and if not tonight tomorrow and I may screw you again tomorrow and were fine.” Lynn made her point, Matt said, “Okay, lovers, sex lovers and friends?” “Yeah, sex partners, friends and co-workers.” Lynn smiled, kissed him and said, “Now how about a third time.” and with that she began to stroke her vagina again with his semi-soft penis.

Becky by now had stopped, and asked, “Is that true?” “What?” I said. “You’re so thick that when you go in me I’ll have an orgasm?” Well by now I had decided to fuck Becky and so I led her to the bed, and said, “Guess you’re going to find out.” She smiled and sat on the bed, leaning back and said, “What now?” I came up and spread her legs apart, kissing her inner thighs as I worked to her labia majora and began to lick them. “Pleasure” was my response. I licked Becky’s labia majora and labia minora and then found her clit hood was open and her clit was hard so found the position of her clit, it was 3 o’clock that drove her mad, and I gave Becky her first clitoris orgasm. She screamed in pleasure on that and it made her super horny.

So I brought myself up to her vagina, and I rubbed my thick dick around her vaginal opening enjoying her wetness and then I slowly drove my penis inside of her vagina. My penis felt her vagina quiver, and quiver again as I drove deep inside of her vagina and again as I drove the base of my penis completely inside of her. Becky screamed again “Oh my, Oh Hell YES!” Her body rippled and sure enough, she found out Lynn was right. I gave her a vaginal orgasm by simply entering her and thrusting several times.

As Lynn as enjoying her orgasm, I kept thrusting my penis in and about 2/3 of the way out and back in. I kept an good and even tempo, building Becky back up to orgasm for the third time in this lovemaking. I saw her pink glow hit her breasts, then her neck, cheeks, and face. She looked at me and said, “This is incredible!” I kept my even tempo up and Becky wrapped her legs around my butt and began to push her feet against my butt. “DON’T STOP! DON’T STOP! GOOOOOOO!” Becky screamed. I felt my cum enter my penis now, and it swelled with that to its final hardness and Becky’s eyes went wild with pleasure. Now she was matching my thrusting and squeezing and suddenly I felt her vagina again erupt into pure pleasure as orgasmic wave after orgasmic wave flooded across her young body. “Cum in me, CUM NOW!” Becky moaned and so I did. I ejaculated deep inside of her vagina. After the eight, ninth and tenth times Becky finally stopped squeezing and I bent down to her and she took my face in her hands, her palms on my cheeks, and kissed me, long and passionately.

“Why the hell does Lynn want to cheat on you?” was Becky’s first statement. “I don’t know, but to hell with it. You’re damn good Becky (she is) so tell you what. Want to make a pact?” “What pact?” came her suspicious reply. “As long as Lynn and Matt are lovers, we’ll be lovers?” “Yeah, I’d like that but I’d like to get married someday and have kids.” “Fine, we’ll screw each other until something comes along.” “No condoms,” Becky said. “Why?” I asked. “I like your dick natural.” “What if you get pregnant?” I asked. “You have the money to pay for another kid.” She was right, it would be nothing to pay her out for 18 years of child support or pay the child support each month. “Yep, so I guess we need to practice.”

By now I had forgotten about Lynn and Matt and looking over, I could see Matt standing behind Lynn and Lynn guiding Matt’s penis into her vagina from behind her. Lynn was slightly bent over, hands on the way except for when she inserted Matt’s now hard again penis into her vagina and Matt was thrusting in and out of Lynn’s vagina from behind. “Faster, harder, yeah harder!” Lynn moaned. Lynn’s butt was moving back and forth in time with Matt’s thrusting of his penis inside of her vagina. Faster they went and suddenly Matt screamed loudly, very loudly as he ejaculated inside of Lynn. Lynn screamed a moment later and kept thrusting back and forth on Matt’s penis. “Cum in me, cum more in me my Matt,” Lynn screamed. Matt smiled at being called my Matt and kept pounding her. “Damn, I don’t care, I love you, Lynn, I love you, I really love fucking you!” Matt screamed as he continued to ejaculate inside of Lynn, his dick completely in her up to its base and his hands wrapped around Lynn squeezing her breasts.

I looked at Becky and I was horny again, really horny and so I came over and asked, “What positions do you like?” “I have only done the missionary and after you, I think I like that the best!” Becky said with a smile. Let’s start with a different position and end in the missionary” I suggested. “Sure,” Becky said. “Which one?” I told her to lay on her side, and then I would lay on my side. I then lifted her leg over me, and I took my penis and held it, it was getting hard again, and I rubbed it against her vaginal area. I also kissed her, and I felt Becky get wet again, my penis was hard as a rock again, and so I gently put my penis head inside of her vagina.

Becky sighed as I entered her. She kissed me hard, her tongue stiffening against mine in my mouth. I drove my penis slowly inside of her, filling her vagina up completely with it. “Yeah, Oh Yeah” Becky moaned. I now slowly and I mean slowly made love to Becky. I a mean made love to her. I kissed her, I rubbed her breasts and my penis would completely enter her, and then come out to where only my penis head was in her, and then go all the way back in. Becky kept kissing me and then kissed my neck and my face, my eyelids as we kept making love.

Becky slowly began to match my slow thrusts and to squeeze my penis with her vagina. We began to increase the tempo, slightly not rushing it. I brought her to orgasm and she held me tight, squeezing me and then as she enjoyed the afterglow of multiple orgasms, I kept making love to her, kept up my tempo. Becky’s vagina responded and she got wetter. She kissed me and then out tongues were interwoven in the air between us and then back into her mouth. We were mimicking our lovemaking with my tongue and her mouth, or vice versa at times.

My tempo increase slightly and Becky was staring at me as we made love, and I at her. I loved her tight vagina, she was young and said she had only had two men in her life, and it had been 6 years since she last had gotten laid. It was time to make up for lost time in bed had been my reply. Now I just looked at how beautiful she was and I told her, “Becky you are so beautiful!” I saw a tear come out of her left eye, and I repeated it “You really are so beautiful.” I kept making love to her as she drew me close, her tongue going in my ear and then “I only want you Jason, only you. Love me, love me completely, make love to me over and over again.”

With that, she kept her tongue in my ear, a total turn on and then she turned my head and kissed the back of my neck. Outside of oral sex or sex, that is my biggest turn on. I grew super hard now, I let the cum flow into my penis and it swelled with the added volume. Becky moved to my ear and said, “Put you in me!” With that my tempo went wild, and Becky matched me and she screamed in pleasure, squeezing my penis at the exact moment I ejaculated in her vagina. Over and over I ejaculated, and she held me, kissing me, tilting her head back, “More, give me all of it!” I gave her all I had over and over as I kept ejaculating until we were both spent.

We laid naked together and Becky said, “I have always wondered what an older man would be like.” “Well, I am not that old,” I said. “Your 23 years older than me, that is older to me.” “Well,”, I said. “How is an older man?” “The best I ever have had.” Becky said smiling. “Lets get out of here,” I said. “Go where?” Becky said. “A hotel where we can be truly alone.” I came back. “You don’t want to watch the Lynn and Matt show?” Becky asked. “No, I want to be the Becky and Jason show.” was my reply. Becky smiled and said “Lynn is stupid. Her loss is my gain.” “Sure is,” I said. We got dressed, I looked at Matt and Lynn who were lying in the bed, naked and making out and talking as I shut the speaker off and closed the curtain. I thought it will be a while Lynn before we make love. I looked at Becky, looked at her tight ass, and got caught doing so. “Yeah, that butt belongs to you. Let’s go put it to work.” Becky took the rest of the day off and from 2:00pm to the next morning we made love, ate, slept a little and made love again. I didn’t come home that night. Becky and I were exploring each other too much.

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? Becky and I have no problem admitting we love sex together, and we are committed to being lovers for sometime. My wife will never be content with one man, she will always be open to another man being her lover. I enjoy Becky more as a lover as she is young, willing to try new things, modify things I know, and man, it is great to make love to a younger woman. More importantly, she is intelligent, kind, good at what she does. Becky and I will be lovers for a long time, and I could end up fathering a child with her, we’ll see when that day comes. Lynn and Matt will be lovers but I don’t think for too long. Lynn told Becky that Matt’s penis is too thin, though its length makes up for it somewhat, but he ejaculates too soon for Lynn, making her work for her orgasms.

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? 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? A little bit

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 found that I don’t have to be monogamous, my wife isn’t and supplementing with a willing partner enhances living and life. Reminds me that we can have multiple partners.

What was the WORST thing about this hookup? Watching my wife make love to another man, her second lover in 10 years. That stung somewhat but it led me to making love to Becky and that has turned out to be a great thing. We have made love everyday since this day.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not too much into multiple partners but I am finding that having a lover that is your lover and friend helps to bring sexual fulfillment and emotional fulfillment to one.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? 5 days in a row we have made love at least once, if not multiple times, Becky and I. Fun to enjoy making love to someone else.

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? More open marriages. Be honest if you need more than what your partner can supply and work it out.

What do you think about the Casual Sex Project? Interesting

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