Saturday arrived, and Jason arrived at our door exactly at the time we had arranged. My husband David shook Jason's hand warmly, and I gave Jason a hug and a small peck on the cheek. We invited Jason inside, and he sat down on the couch. I sat next to Jason, and David sat on the comfy chair across from us.
David began the conversation with a little monologue about consent. From there he moved on to safe sex, contraception, STDs, and so on. David asked Jason if he had ever tried putting on a condom, and Jason sheepishly shook his head: "No, as I told you -- I am still a virgin."
David, smiled and replied: "Don't worry, Jason. There is a first time for everything." David stood up and left the room, and headed upstairs. I wasn't sure what he was up to, so I just looked at Jason, smiled and shrugged.
Two minutes later, David returned with a wrapped condom between his fingers. "Here you go, Jason. Samantha and I have a little stash of these from when we would still use condoms, early in our relationship. Why don't you take this to the bathroom and try it on. You need to make yourself hard first, and then open the package and roll it down the shaft." I was a bit taken aback by the entire scene, but at the same time quite turned on by the thought of Jason making himself hard in our bathroom and trying on a condom for the first time. A condom I had originally bought to use with David, years ago.
Jason smiled an embarrassed smile, and took the condom from David. "Thanks David. I'll give it a try."
Jason, left the room for the bathroom, and David looked at me and winked. I smiled coyly, and silently mouthed to David: "What on Earth were you thinking?"
David shrugged and smiled back: "It's all part of our responsibilities as sexual mentors." I gave a little giggle, and sat back to wait for Jason to return.
As we waited for Jason to return, my mind kept imagining Jason standing in our bathroom rubbing himself to get hard, and trying to put on the condom on his virgin cock for the first time ever. The room began to feel warm, my face began to feel flushed, and my pussy began to tingle. After what felt like forever, I heard the handle of the bathroom turn, and Jason return bright red in the face. "It wouldn't go on" he sheepishly told us.
"What was the problem?" David asked.
"I don't know" replied Jason. "I couldn't figure out how to roll it on."
David laughed, got up from his seat, and went over to Jason to pat him on the shoulder. "Don't worry, my boy. I'll go get the condoms, and Samantha and I will give you a little demonstration." With that, David left them room and went back upstairs to our bathroom to fetch the condoms. I felt completely flustered, having no idea what would come next. I smiled at Jason, completely flushed in my cheeks, then looked down at my shoes as I waited for David to return.
David soon returned, with the whole box of condoms in his hand. There were a few left that we hadn't used, and David sat down in his comfy chair, and motioned to me and Jason to come over to him. David smiled at me, motioned to his crotch, and said: "Come Samantha, let's show Jason how its done." I was both incredibly embarrassed, but also turned on. Jason and I walked over to David's seat, and I kneeled next to David as Jason stood over us watching intently. I opened up David pants, put my hand in his underpants, and took out his cock that was already beginning to harden. I slowly began to stroke David's cock, which responded with a strong erection after about half a minute. David opened the box of condoms, took one out, opened the package, and handed it to me. As I rolled the condom on David's cock, David explained to Jason how one positions the condom and rolls it down the shaft into place.
Jason looked a bit puzzled, shrugged his shoulders, and said: "I don't know. You guys made it look so easy. It didn't work for me like that."
David, with his sheathed cock still standing upright, motioned for Jason to sit down on the couch. "Samantha, take another condom and show him how it's done." My heart skipped a beat, as David's words sunk in. I was so turned on by the thought of giving Jason a "hands on lesson", but extraordinarily shy at the same time. Jason hesitated a second, and then walked over, and obediently sat down on the couch. "Go honey," David motioned as he handed me a condom in a package. "Show Jason how to put on the condom."
I took the condom from David with my shaking hand, and then hesitantly walked over to the couch and kneeled by Jason's legs. I carefully opened Jason's pants, put my hand into his briefs, and slowly took out his cock. Jason's cock felt heavy in my hand, and as I took it out it began to grow immediately between my fingers. Soon it became apparent why Jason had trouble before, when he tried putting on the condom. His cock was huge! Clearly the condoms that David and I had been using were going to be too small for Jason. David looked over, and let out a hearty laugh: "I think I understand what went wrong, Jason. Your penis is too big for our condoms! You are going to need extra-large ones!" David, Jason and I all burst out laughing, and the awkwardness in the air soon dissipated.
After our laughter died down, I found myself kneeling on the floor between David and Jason, with both of their cocks standing at attention. David pulled the condom off of his penis, and started to rub himself, and Jason started to rub himself as well. I was the only one fully clothed, but I was feeling incredibly horny, watching my husband and this young man pleasuring themselves in my living room. David broke the silence: "Samantha, what do you say that we all go up to the bedroom and you and I will give Jason a little demonstration."
