So my exwife Anna was a checker at a small grocery store and she was super close with all of her co-workers. There was one girl named Samantha that I was always hopeful there was a possible threesome with. She looked similar to Anna but a little bigger in the ass and Sam had bigger boobs. It was my fantasy to sleep with Samantha and Anna together, but I never let Anna know this.
Anna and I had had sex with others including other couples and another male. We were open to swinging and there was now issue. Because she was nice to everyone she was a bit popular with all of her coworkers. One of her coworkers was really in love with her. His name is Daniel and he was just 18. He turned 18 three weeks earlier, and was a bit awkward. Anna was nice to him because he was a good kid. I actually liked him as well because he was super nice and respectful. We invited him over for WWF events and he was super chill.
He called me in April and asked me if it was ok if he took Anna to his prom because none of the other girls accepted. He felt it would be best if he took someone more mature to The prom and asked me if he could ask Anna to go with him. It would be great for his reputation. I I had to think about it but I felt like He was safe because he was nerdy and wouldn’t do anything. She said he was a super nice and a virgin so no worries. I agreed and she said she was happy to go.
The day before she goes to buy a dress, which is really cute because it shows off her breasts, which weren’t big, but it really showed off her ass nicely. I walk in and she’s getting ready. She’s wearing a black bra and a black g-string. I asked her why she’s wearing a gstring and she said theres no need to have panty lines. I said what did it matter, she said she always wants to look her best. Plus what’s the point of being around horny teenagers if she can’t be a bit of a tease.
I was ok with it, I had no issues because I definitely liked her flirting. She got all dressed up and I wanted nothing more than to fuck her right there. But before I could make my move Daniel pulled up. He borrowed his brothers cara really nice Mercedes’, and she appeared to be impressed with it. She said when she gets home she’ll need to get laid. I agreed 100%. Dan came up in his tuxedo and looked as dapper as can be. He gave her a corsage and flowers.
I told him when he brings her back to come up with her to make sure he was ok to drive home. He agreed and I told him we’d call his mom if he didn’t come up. He thanked me again and shook my hand firmly like a gentleman. I felt he would be protective of Anna If need be.
While at the dance I went to a bar close to the house and she called me after a while. She let me know that she danced with not only Dan but his friends too. She told me Dan had the biggest cock of all 7 guys she danced with. I asked if she wanted something with him. She said he’s a virgin, and she wanted to take his virginity if his dick was as big as she felt. I told her to bring him up and we’ll see if it can happen. My mind started racing. I had a few shots and a few beers and decided to head home. I cleaned up the house and went through her clothes and found some really sexy panties she has as well as short PJ shorts and a super short tshirt to have her change into. I left her a note in the closet to let her know how I would like to make her plan happen. I told her the signal if she wanted it to walk out putting her hair up.
At 2am I hear him pull up and since I told him to come up after the dance he joined her. She went into the bedroom to change and I figured I would ask him to stay in the extra room. She walked out putting her hair up in a pony tail. This was my sign.
Because he drank a little. I called his mom and let her know I didn’t feel good about him driving home because he was tired. He could sleep in our extra room and we would send him home tomorrow after having a good nights sleep and lunch. She was suuuper thankful and said she felt great we were looking outside for him. If she only knew.
We knew Dan was going into the navy right after high school and was not looking for a girlfriend. When Anna came back out she was wearing the tiny shorts and small shirt I laid out for her. She sat next to me on the couch and I let her know I talked to his Mom and he was staying over. She said it’s for the better.
She tells him he’s free to have a beer since he’s staying over. He agreed. He said he only wanted to have 1-2 so he doesn’t have a hangover in the morning. I let him know he was not going to have a hangover we would take care of him. He seemed very appreciative and Anna disappears into the kitchen. I tell him I’ll be right back, and he said ok.
When I get into the kitchen I pulled her shorts away and see the same gstring she wore to the dance. I asked why didn’t she use the other one. She said this one is wet and she wanted to keep that wetness on. I said ok then.
I bring out Dan his beer and he starts drinking it immediately. She sits next to me on the couch and drinks her red wine faster than she should be. We start to talk about the dance and what happened. He gave me the PG play by play. She tells me that’s most of what happened, except they danced all of the slow songs together.
He turns red but she addresses is and asks why he’s embarassed. She REALLY liked those dances. I ask him if he liked them too. He tried giving a PC answer. I ask her WHY she liked the slow songs so much. She said it was because she knew that he appreciated the dances and it was REALLY REALLY obviousHe kept trying to play it off, but I wasn’t letting it go. I let him know that I wouldn’t be mad because she’s sexy. When I said that I squeezed her breasts to let him know it was ok to be honest. Anna tells him I am not the jealous type at all and to be honest.
He said that he had an erection during the slow dances because she was grinding on him, and I could tell that he felt very ashamed of that. I let him know that I know how it goes because she’s really sexy and I always have a boner when she dances with me. I asked him if he had danced like that with another girl, he said, not since Jr. High. I said it’s different with a woman who knows what she’s doing. He said it definitely was. She admitted to him that he has a really big penis and she’s surprised that no other girl has tried it out yet. I could tell he was nervous because he slammed his beer. She offers him another and he accepts. I tell him I’ll be right back.
I assure her I’m still in and if she wanted I’ll take a leadership role and tell them what to do. She said that was perfect. I told her I was gonna go to the bathroom and to Take the first step. She said no problem. When I come back in she was sitting next to him on the couch. He was obviously nervous about this. I sat down in the recliner he was sitting in.
So I asked her if he was bigger than she had ever had. She said definitely. He was starting to turn red. I asked why he asked Anna and not another girl. He said he liked her and it would be good for him if he took an older woman to the prom and maybe another girl would go out with him and he could try and lose his virginity. I asked why he didn’t try to lose his virginity with another girl tonight. He said he didn’t plan it out well enough. I just said it to the room to say it is that every virgin should lose their virginity on their prom night. He said he was just trying to think ahead.
I changed the subject which I think he liked. I asked him when he goes off to the Navy. He said that he was off to basic training in three weeks. I asked if he gave notice at work and he said that he did.
Anna looked at me and smiled. She knew where I was heading with this. I asked Dan if he thought he was going to be able to keep national secrets once he was in the Navy. He said, definitely. There are plenty of things he knew that he kept to himself. I said that was good. He asked why I asked, and I let him know that if he can keep everything to himself, we had an idea we wanted to run by him.
He said no problem at all. He keeps his business to himself, and Anna agreed that he doesn’t participate in drama and rumors at work. She gets up to fill her wine, and I follow her into the kitchen.She’s pouring a huge glass of red wine which means she’s really ready to proceed. I ask her if she is 100% certain. She says why is she pouring wine if she’s not ready. I asked if she could do him without condoms since he’s a virgin and she’s on birth control. She asked me if I’m sure. I said yes. She warned me that his cock is HUGE and thick. I told her that the more she enjoys it the more that I will. She asked me if I’m sure. I said yes of course. She tells me to take control, and she will go with it. I agreed, and we both walked back in. I had a new beer and she had a half a glass of wine. Which to her means she will be out of control because red wine makes her not only horny but also a little aggressive, I feel good about this. She said she’s going to go into the bathroom and get ready. I tell her I’m going to get the ball rolling. She said she’s gonna give me 5-10 minutes and I better have things moving.
I walked back into the front room and things get more frank. I tell him that everyone should lose their virginity on their prom night. He asked what I meant. I told him that Anna was interested in taking his virginity tonight on 4 conditions. He was shocked. I laid out the rules:
1) NOBODY at the store that they worked at could EVER know. Once he was in the Navy, he was free to tell anyone that would listen as long as he doesn’t mention Anna by name. He agreed.
2) She was in control in the bed. Whatever she said goes. I will lead them, but she’s the boss. He agreed again.
3) This is a one night thing. No matter what when he leaves that’s it.
4) That he didn’t have to use a condom because he was a virgin and she was on birth control.
He balked at that a little, but I told him that every man’s first orgasm should be inside of a pussy. Eventually he agreed and asked if I’m sure about this. I told him to go into our bedroom and get Maher to his underwear. He said ok, but he wanted to make sure I wasn’t going to beat him up. I told him he’s bigger and I wanted her to try a big dick, he needs to lose his virginity and deserves a tight pussy, but one that’s experienced. Anna was the best choice. He agreed and said he masturbated to the thought about this. I warned him that his first time would be fast. It’s nothing to be ashamed of. The second, third and fourth times will be better. He asked if he was able to go multiple times. I said he can go until he’s unable to perform anymore.
I told him to go to the bedroom, close the door and strip down to his underwear and sit in the chair at the edge of the bed. He said ok. He goes in and closes the door. She hears this and walks into the room where I am. She asks if everything is ok. I explain the situation and she smiles. One last time she asks if I’m sure this is ok with me. I assure her I want to see her take his virginity and then try and fuck him until he can’t go anymore. I wanted to see his first load leak out of her and then they can decide where the others are. She can him where the other’s go. She kissed me and said, let’s go.
I smack her on the ass and kiss her. I tell I love her and I’ll love her just as much if not more if she shows this young man the time of his life tonight. I let her know that I told him to cum in her for the first one. She said she will make sure he cums deep inside her. I told her that is the hottest thing I’ve ever heard and to make me proud. She asked what I meant. I said if she can make him cum 3+ times tonight and again in the mornings at least once, I would be so proud of her. She smiled and said she’s gonna take everything he gives her tonight and tomorrow. I told her I will kiss her pussy when he’s done and try out her stretched out pussy. She said she’ll make me proud.
She opens our bedroom door and he is sitting in the chair with boxer briefs, albeit with an enormous erection. I was not prepared for the size of his cock. For a moment I had a thought that we should stop. I was definitely jealous of his cock and she looked at me and looked at me for approval. Everything in my body said to stop, but I shook my head yes. She told me to tell us what to do. She asked if he was ok with me taking pictures. We would share the pics with him of the first penetration, because there would be no faces. He said he was ok with that. I turned on the video camera, and grabbed the digital camera. She was standing in the doorway and he was about 15’ away, but their eyes were locked on each other.
I asked if he was ready he said, I think so. I asked her the same and she says, I think so. She tells him it’s kinda like they’re both having firsts tonight. He looked at her confused. I said I’m pretty sure she means that she’s never had a dick as big as yours. She confirmed that he’s MUCH bigger than she’s used to – meaning me. He looked puzzled so I made it clear. I think she means your cock is bigger than mine and she’s never had a dick that big, just like you’ve never felt a vagina. She confirms. “I am not sure you know how blessed you are. I’m a little afraid of your cock.”
He smiles proudly and looks at me for what to do next. I let her know to go over to him and let him remove her top and shorts. She sheepishly smiles at him. I ask him if he likes ass or tits more. He said he wasn’t sure. He’ll let me know in the morning. She smiles and says good answer. I tell her to go to him and let him take off her top and shorts. She walks over to him slowly and he pulls down her shorts first. She moves her pelvis closer to him and he is still nervous, I can tell. I tell him to kiss her belly button. He did and she moaned in approval. I see his hands squeeze her ass and move her closer while he is kissing her belly. She looks at me and her eyes and smile tell me she’s enjoying it. “I think you should teach him how to eat pussy. Girls will owe you a huge debt of gratitude.” I agreed and asked her what she meant. She said to show him how to do it and then let him try it on his own. I thought that was a great idea, but I thought it was a good time for him to take off her top and enjoy her breasts. He stood up and helped her out of her top. He sat back down and squeezed her tits really hard. I instructed him to be firm, but not too hard. He took the advice and it was obvious she liked the pressure. I let him know that he should kiss between them and try kissing her nipples, but to use the same theology. Firm but not too hard. He moved to the left nipple and sucked on it. By her response, he definitely understood the mission. I told him to try the other. He did and he once again hit the target.
This went on for a couple of minutes and I instructed her to get on her knees and show him and his big dick some appreciation. I told him to stand up and she kneeled in front of him. She looked at me and I told her to unwrap her present. She pulled down his boxer briefs and I think the size and veininess of his cock even surprised her. She looked at me for approval. I told her to touch it. She started to give him a hand job, but she wanted to call attention to something different. She said his balls are so big and full. She asked the last time he came, he said it’s been 2 weeks. She looked at him shocked. He said he almost came during the last song they danced together. She smiled and said well then he owes her an orgasm.
He said he is almost ready to go. So she said that I should teach him how to eat pussy. I showed him all of the secrets I knew. I showed him where the g-spot is and how to manipulate it, and how to manipulate the clitoris so the woman would orgasm. I told him to try. It was a little awkard at first, but she guided him on where to go, and She definitely was appreciating his technique. She asked me if I wanted her to give me a BJ, I said no. Pay attention to your lover.
She understood the mission and pushed his head up. I told him to lay down on the bed and she’s about to give him his first oral. I let him know that she’s very good at it and if he feels like he is about to cum to tell her to stop. He lays down and the length and girth of his cock makes me really question this. She crawls over and kisses the area under the head of his cock. He is obviously liking it. She puts the head of his cock in her mouth and starts to slide it down her throat. He tells her that she has to stop. She smiles and says it’s that good huh? He said yes. She asks him if he’s ready. He says, and they start kissing. She throws her leg over him and straddles him. I can see his cock is super red and her pussy is super red and puffy.
I can hear them kissing. His hands are squeezing her ass, spreading it apart. I asked him if he was ok if I grabbed his cock and guided it inside her. He ok’d it, so I grabbed it an inch under the head with one hand and used my other hand to spread her pussy to prepare her to allow him in. His cock was ready, there was so much precum and her vagina was literally glistening. They were ready. I put his big cock head against the entrance of her pussy and told her to take it. She positioned her vagina and his cock started to disappear into her. First the head, and she made noises I’ve never heard from her, then half goes in and she noises are reminiscent of a porno, then ¾ and he said to stop for a second. She abided. He said he’s so wet and tight. She said it is because his dick is so big and that she likes it.
After a few minutes, she sits up and takes as much as his dick as she could. She starts sliding up and down and within 2 minutes he said he’s going to cum. She said very forcefully, INSIDE and starts grinding harder. His hand slap her ass and squeeze hard and I can see his balls tighten up and from the remainder of the dick outside I can see his dick pumping his sperm into my wife’s vagina. As he’s cumming, she leans down and starts kissing him deeply. I let them kiss for a while and I told him to turn her over onto her back and to put her legs up and point her vagina towards the ceiling. He does and removes his dick. Her pussy is completely open and I can see thick creamy white cum inside her. She looked over at him and said your virginity and babies all belong to me now.
He said he was ok with this and said he was going to go to the bathroom. He walked out of the bedroom and I kissed her open vagina. I didn’t stick my tongue in, but she said he felt incredible. She said I was right that size makes a difference. She asked me if I wanted to try out her sloppy seconds, and I let her know I would fuck her when they were done for the night. When he walked away, he still had a huge erection. I knew that this meant that he was going to want round 2 as much as her and I did.
He returned to our room without an erection. He asked if I would fuck her so he sould get new ideas. I said sure, and took my clothes off. After seeing his cock I was definitely a little intimidated. She got on all 4’s and I slid in and there was little resistance. I could feel his wetness in her. I knew it was him and within 5 minutes, I was about to cum. I pulled out and came on her ass and up her back. I rubbed my cum into her and I looked over at him and his huge cock was hard as a rock again. I told him to try and break the back wall. She said if he fucked her too hard he would. He smiled and guided his dick in. Again, she made noises that were so sexy that my cock got hard again.
This time he lasted considerably longer. Long enough for her to have a huge orgasm. This was as much as he could take and ha pushed all the way in and came. I could see his balls tighten and loosen once. I was watching another man cum inside my wife. He then pulls out and shoots 4 thick ropes of cum up her back and down her ass. He backs away from her and I take the opportunity to rub his cum into her back and ass just like I did with mine. He collects his clothes and goes into the spare bedroom. Anna slumps down onto her belly and coos.
“Wow” I am not sure if this is what you’re ready to hear but that was incredible. I let her know I wanted her to experience this and she brought me to her and we kissed. We were making out deeply. She was thanking me for the moment. I told her I thought he was done for the night. She said she wanted to taste his cum. I walked to the bedroom and the door was open and he was in the bathroom. He walked out and I let him know she wanted him to cum in her mouth before he goes to sleep. He said ok and follows me back into the bedroom. I instructed him to lay down and let her do her thing.
He lays down on the side that I normally sleep on and starts kissing his cock seductively. By the 4th kiss his dick is rock hard again. She spent the next 15 minutes sucking his cock and sucking on his balls. He is obviously liking it but he’s not ready to cum yet. She lays on her back and tells him to take it. He wasted no time and slid his dick in and started pumping. She tells him when he’s close to let her know she she can suck it out of him. He said anything for you baby. He spent the next 22 minutes fucking her at different paces and depths. I’ve never seen her cum as much as she did then.
He said he was gonna cum and she said to shoot it in her mouth. There was about an inch between the tip of his cock and her mouth. He let go and it was so thick and looked like was shooting yogurt in her mouth. She showed me all of the cum in her mouth and then swallowed it all. She cooed to him, mmmm you taste so good.
He says he doesn’t think he can go again tonight, and he was going to go to bed in the other bed so we can have some time together alone. I told him if he wakes up early to come in and we can maybe both do her. She said maybe a DP. I have never heard anything hotter in my life. He walked to her and kissed her passionately and hugged me hard. “Thank you so much.” I could feel his cock pressing against mine and I was a little intimidated again.
He walked out of the bedroom and I could hear the other bedroom door close and I knew that was all he had.
I turned to Anna and asked if I could have my turn. She said she was VERY sore and very full. But if I gave her some oral she’d give me some. I gave her the best oral I’ve ever given her. Sucking his semen out of her her giving her an orgasm in the process. After this i wanted to feel her. Her vagina is normally tight but now I could feel the damage he did to her. I fucked her for a solid 20 minutes the only orgasm happening when I told her how hot it was to watch her take his virginity. There was definitely sperm competition because I’ve never cum that hard in her.
We kissed for the next 15 minutes and she told me how much she appreciated what I let her do.
We slept like babies until the sun came up at 6:30. He crawled into bed with us and she was sandwiched between us both. I woke up to them sleeping with his arm around her and his dick poking between her legs.
We all slept until about 7:15 when I woke up than they were both gone. I knew they were fucking somewhere but I just didn’t know the situation. I opened the bedroom door and Anna was riding his big dick on the sofa where it all started.
I watched for a minute or 2 and I realized that her once tight vagina has become used to his penis because at the end of his stroke he was balls deep in her. He noticed me and told her I’m there. She looks back at me and smiles. She asks for me to go get a condom and lube. I asked why are you making me wear a condom. she said she is ready to try what I’ve always wanted to try. I said “DP?” She said now is the time to try it. I walked back to the bedroom and slid on a condom and lubed my cock and her ass. The kid that was a virgin and my wife was his prom date 12 hours before, put his entire cock in her and she let out a guttural moan.
I gently slid my cock in her ass and I could feel every detail of his cock against mine. The three of us found a rythum and she came incredibly hard. I wasn’t far behind, but I pulled out and added to the 2 now crusty loads on her back and ass cheeks.
He said he wasn’t ready yet. He asked the options, she said we can take a shower alone, he can cook us breakfast and you can head out afterwards.
He asked me what I thought and I said that would be great. Before she got up, I rubbed my cum into her back and ass. She stands up and they walk into the bathroom. I hear the shower start and I start making breakfast. I hear them fucking and her enjoying it.
By the time they finish they both walk out naked and I give them breakfast. We all eat together and it’s super quiet. He goes into the bedroom and puts his tux back on. He comes back out and shakes my hand. Thanks me and then kisses her and says this is our night and thank you.
He confidently walks to the door and walks out the door.
She looks at me and asks if I’m ok. For the next 3 hours we had sex and it was the best sex we had together. After we were done she said she felt happy that she took a boys virginity. She was concerned about how I felt and I’ve never felt more attracted to my wife than I did at that moment. She was the sexiest woman in the world and my favorite porn star. Full of virgin cum.
Source: reddit.com/r/gonewildstories/comments/uv7yav/my_now_ex_took_a_boys_virginity_on_his_prom_night