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Backstory: I (late 30s) have been with my wife(early 40s) for going on 7 years, married for 4. I found out before she met me she had a MFF with her boyfriend and a mutual friend in college. Jealousy got involved, and that turned her off of the idea of adding someone else for a long time. We started out like any relationship- by sending each other risky texts or pics. She has a friend (mid 30s) shes known for over 10 years, and they annually go on a cruise together. I’ve admitted to her I’ve had lots of fantasies involving her and I and other people (including her friends and mine). I say all this because what all led to last Saturday night started on one of those cruises. Her friend was tired and went to her room early, leaving my wife bored out of her mind, she texted me complaining. I then proposed I start an erotic story and we both add to it to keep her mind occupied. The story involved many people, and we ended up with hundreds of screenshots of this story we created. When she returned from the cruise, she admitted she was so turned on by this story we created, that we fucked immediately. A few weeks went by, with us still adding to the story. During those first few weeks back we went at it every day, something we hadn’t done in years.
We went on a beach trip with some of our friends (all married, early to mid 30s) not long after, and the whole time we spent away from them discussing making the story somewhat a reality.
We decided that we were wanted to add someone else to our fun, but she didn’t want it to be a random stranger. The only friend we both could decide on wasn’t even at the beach with us that day, he’s also the only single guy in our friend group. I met him thru work, and he ended up being the best man at our wedding. The problem is…..he’s 23. He’s never had a real gf, never even seen a woman naked. He is very shy, and works constantly….so he doesn’t even try to find himself a woman. We did set him up on a blind double date once with one of the wife’s coworkers, but it didn’t work out. I originally pitched the idea to him of a threesome within a month or 2 of her cruise…and he turned it down. Stating that the age gap was too much for him, and that he wouldn’t even know what to do because he’s never been with a woman before. But he did admit he thinks my wife is cute, and has checked our her tits once or twice at some of the friend get togethers.
Fast forward to last Saturday night:
He invited me over after work for some alcohol and video games, as he was worn out from wrenching on his project car. We’re chilling and the subject of him finding a girl comes up “I dunno man, I know women my age…..not my type. Most aren’t even the same political party as me.” He said as he threw his head back and sighed. “And most don’t even want a guy who’s inexperienced and short. I don’t want to end up being 35 and a virgin….. hell I don’t wanna be 30 and have not even have seen a pair of tits. I’ve spent so much time working on this project car…..to have someone to ride passenger princess….but I ain’t even been on but one date…the one you setup.” He paused for a few minutes. “I should have taken you up on that offer…. But I gotta ask……why did you pick me…..out of all our friends?” I responded….”Because…..you’re most like me….. and the wife thinks your cute.” He thought for a second as he took another shot, “Well…..if I had done it…..at least I’d have some confidence and maybe I’d actually start talking to some women after. And if it didn’t go….well…..perfect……at least it’d be with people who wouldn’t judge me.” He thought for a bit longer and then finished by saying “Fuck…..I really shoulda done it……I should have…..but the offer is probably gone.” I pulled out my phone as I said “The offer’s not gone….I could text her right now and have her come over after work.” He thought I was joking. I texted her letting her know he changed his mind and showed him the screen before I hit send. He looked shocked for a second. She texted back “Is he sure or is this the alcohol talking?” “He’s serious” I replied. A few moments went by and those three dots on the screen before I saw her reply. “Ok…..I’ve got a plan. I’ll come over right after work. We gotta take this slow tho….tonight just some foreplay…..to make sure it’s just not him drunk. See how he feels the next day….If he feels the same…..we’ll introduce him to the card game.” We own a few of them couples card games….but one sticks out because we used it on our last vacation to TN. (It’s essentially all dare cards that you do to one another. I don’t remember it’s name as I type this….but I can include it in the next update).
She arrives a little after 1am. We all sit in his living room on opposite couches…..and we talk. She confirms he’s pretty serious….but still wants to take it slow. She tells him tonight, no sex…..but if this goes well the next time yall are working on the car I’ll stop by and we can finish where we leave off. He agrees and then she stands up and walks over to him. She curls her fingers under the bottom of her work shirt and asks “I hear there’s something you might like to see.” He nods very enthusiastically, and she lifts and removes her shirt- her nipples are already semi- hard on her D-cups. He reaches forward and begins to gently caress them. As his thumb glided across her nipple, she let out a soft moan. I sat there watching for a few….my erection growing with every second. As he continues, her moans increased and she stumbled forward. She gets on her knees next to him on the couch as he begins to let his tongue explore her breasts. After awhile of watching I get behind her and begin to kiss her neck. My hands tease the nipple of whichever one he didnt have his mouth on as he switched between them. She notices his bulge thru his shorts, and slowly she brings her hand to it. As she stroked him thru the fabric, she turned her head and whispered to me….”Baby…..he’s thick…….thicker than you.” My mind raced with thoughts of him stretching her walls. I don’t remember how long this went on for….but he came after her hand finally found its way down from his hairy chest to underneath his shorts. We relaxed together for a bit after…. but I insisted she drive me home since I’d been drinking. On the ride home…..she admitted that he was certainly larger than she had expected. He’s roughly 5’3 but he’s carrying a good 6-6.5 inches that are thicker than a red bull can. She teased me with thoughts of her riding him on the couch, or blowing him while I tease her clit from behind. We went home and I fucked her, her being wetter than anytime since that trip to TN.
I started a group chat for us 3 Sunday morning, so we could discuss anything related to the night before. As the wife and I are finishing lunch together, both our phones light up. My friend “Is there anyway the 3 of us could take a night ride in the project car next weekend?” The wife looks up from her phone at me with a devilish look on her face. “How’s next Saturday night?” I reply…..
So next Sunday I will have part 2.
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