Mentoring a Young Man Pt. 02

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."

I looked at Jason as if to question whether he was OK with this, and he shook his head "yes" as he slowly worked his hand up and down his long shaft. I looked back at David, and coyly said: "OK honey. If you think this is a good idea."

David stood up first and took his pants completely off, and Jason followed his lead. David took my hand and helped me up from where I had been kneeling on the floor next to Jason, and led me by the hand upstairs to our bedroom. "Come, follow us" David said to Jason. Jason obeyed my husband's order, and followed behind us, cock in hand. My pussy was aching to be filled by one of these hard cocks that was accompanying me to our marital bedroom. When we reached the bedroom, David ordered me to lie on the bed, and ordered Jason to stand next to my head. As soon as I lied down, David stood at the end of the bed, pulled me by the legs toward him, and slowly began to penetrate me with his hard cock. "Watch carefully" he said to Jason, and Jason leaned over to watch, rubbing his cock the entire time.

My pussy was so wet, it easily devoured David's hard cock. David began by making slow love to me missionary style, and as he did so, he explained to Jason exactly what he was doing. "You need to make sure that the woman is wet and ready, and then start off real slow. Monitor her to see if she is ready for you to pick up the pace." Jason nodded in understanding, as he watched us, rubbing his cock with a mesmerized look on his face. I kept switching between looking deeply into my husband's eyes, glancing over to look at Jason's youthful and curious face, and then down to Jason's large cock as he stroked it in his right hand. My pussy felt like it was going to explode.

Just then, David pulled out, and told me to stand up. I obeyed. David then lay on his back on the bed, and ordered me to ride him cowgirl. "Jason, you go stand at the end of the bed, behind Samantha, so you can get a good view." Both Jason and I followed orders; as I climbed up onto David and straddled him, Jason moved to the foot of the bed and stood directly behind me. I guided David's cock into my ready pussy as I sat down on him, and started to ride him. David looked past me toward Jason and said: "When you are in this position, you can tell exactly what stage your girl is at, by how hard she rides you. As the man, you need to constantly be in control of the pace" David explained to Jason. With Jason behind me, I could not see his reaction--all I heard was a grunt of understanding. Knowing that Jason was standing behind me watching me fuck my husband turned me on like nothing else.

After a few minutes of riding cowgirl, David pulled me toward him to kiss me passionately, which forced my ass into the air and his cock to slip out. I knew that my bare pussy was now completely exposed to Jason, who was jerking off directly behind me. All I wanted at that point was for my pussy to be filled again. And yes, I must admit, that I yearned for Jason to penetrate me with his big cock then and there. I could hear Jason vigorously pumping his cock with his hand, and my pussy ached for it.

After David finished his passionate kiss, he pulled me even closer and whispered into my ear: "Shall we invite Jason in?" I froze, and didn't know what to say. Was David reading my mind? Was this a test?

"But we don't have a condom for him. Ours don't fit on him."

"I know honey. But Jason is a virgin, so he is clean. And you are not ovulating now. So it is not a problem."

Hearing those last words, I understood that David was completely OK with me being penetrated and filled with another man's penis. My pussy was aching to be filled. I hesitated, and then blurted out: "If you think it is OK honey." David pulled me close again and kissed me again with enormous passion.

David, looked past me to Jason, clicked his fingers, and directed him to put the tip of his penis at the entrance of my very wet hole. "Just the tip" David commanded. I felt Jason approaching me from behind, and then felt the tip of his cock touching the outer folds of my pussy. A million thoughts were rushing through my mind at that moment. Was this actually going to happen? "I will tell you EXACTLY what to do, and I want you to follow my instructions very carefully. OK Jason?" David instructed in a clear and stern voice.

"Yes Sir" I heard Jason reply from behind.

The scene must have been surreal for any innocent bystander, observing from the side: David, lying on the bed on his back, his legs bent at the knees over the foot of the bed, and his feet on the floor. Me, on my hands and knees on the bed, hovering over David, my face directly above his. And Jason, standing at the foot of the bed directly behind me, with his hard cock at the entrance of my exposed pussy, ready to penetrate me doggy-style. "Honey" David looked up at me, and said in a firm voice. "We are going to show Jason what a real pussy feels like. This will be an important lesson for Jason. I want you also to follow my instructions very carefully. OK Samantha?" I bit my lip, looked straight into my husband's eyes and shook my head in agreement.

"OK Jason," David instructed. "I want you to slowly push your penis into Samantha. Very slowly. Enter about two inches and then stop". Jason hesitated for a second, and then I felt the broad head of his stiff cock begin to push aside the folds of my pussy, start to stretch the entrance open wide, and then enter me. The sensation of pleasure which drove through my body forced me to arch my back and let out an audible moan. "Are you OK love?" David asked sweetly. I quickly shook my head yes. "OK Jason, two more inches. Slowly!" Jason slowly pushed his ample cock deeper into me, stretching the wall of my vagina as he went.

"Now if you feel like you are close to cumming" David instructed Jason, "You have to stop moving and focus your mind on something else, like school work. Your job right now is NOT to cum. Do you understand, Jason?"

"Yes Sir. I understand."

"OK, then I want you to push inside another two inches. Slowly!" I felt Jason pushing his cock deeper into my body, and the pressure was both slightly painful and at the same time mind-blowingly pleasurable. "Does it hurt, honey?" David asked.

I bit my lip again. "I'm OK" I said, not sure if I should admit how good it felt to be filled with six inches of Jason's enormous cock.

"OK, Jason. You can now push your penis all the way inside Samantha. Go slow, because you are very large." I felt my pussy filled to the limit as Jason proceeded to slowly push the final inch or two of his cock into my hole. The thought that I was altruistically providing Jason with his first experience of a real pussy, mixed with the overwhelming physical pleasure of being completely filled with a rock-hard cock, turned me on like nothing I had ever experienced before. All I wanted to do at that moment was to rock back and forth on Jason's cock and make him explode inside of me. "Samantha, don't move" David ordered. "Jason, I want you now to slowly pull out and then at about the halfway mark, slowly push back inside. Work your penis inside of Samantha's pussy like a piston, in and out, in and out. And remember, if you feel like you are about to cum, stop moving and divert your mind to school work."

I felt Jason begin move his hips to pull out, and then push back in, just as David had instructed him. The movements were a bit jerky, but the pulses of pleasure that were racing through my body made up for any slight awkwardness. After about a minute of this slow, deliberate fucking, I felt Jason's penis grow even stiffer, and then Jason suddenly stopped moving. "Good boy," David called out. "Stay like that, without moving, and count to ten. When you reach ten, quickly pull out completely."

I heard Jason from behind counting quietly, with a quivering voice: "1, 2, 3, 4, 5, 6, 7, 8, 9... 10!" and then suddenly felt him pull his penis out of my vagina in one quick movement. One second later, I heard Jason let out a soft moan, and immediately afterwards I felt several warm streams of liquid shooting all over the skin on my back.

"I am so sorry Sir!" Jason blurted out with a horrified tone of voice. "I didn't mean to cum like that on your wife".

"What a cute thing to say in the situation!", I thought to myself. The boy's inexperience and naivety were just so adorable.

"Go take some of the paper towels here on the nightstand, Jason, and clean up the mess you just made" David instructed with a reassuring smile. Jason dutifully obliged, brought some paper towels, and with shaking hands wiped off the cum he had just shot all over my back. "Good boy, Jason. And Good girl, Samantha. You did an excellent job giving Jason his first experience of real live pussy. You make a great teacher, but now you deserve a proper fucking as my wife."

With that, David immediately drove his penis back up into my well-stretched pussy and began to mercilessly pound my hole with a force I had never felt before. The ferocity of David's pounding felt to me like my husband was reclaiming my body and staking it out as his own personal territory. After two minutes of pitiless fucking, I felt David tense up and then explode, shooting his load deep inside my womb. The entire experience left me completely drained of energy, and I quickly collapsed onto David, and then rolled over onto the bed next to him, as he embraced me in a tight cuddle.

After a minute or two, David broke the silence and looked up at Jason, who was standing next to our martial bed, stark naked with a semi-hard penis. "Is this what you imagined a real pussy would feel like, Jason?" David asked.

I looked up at Jason, and as I made eye contact, he turned bright red and blurted out: "Um, I don't know. It felt kinda different that I thought it would."

"But you clearly liked it" I teased him, and we all broke out in laughter. It was just the joke we all needed to ease the tension after this unplanned turn of events.

David and I got up and went to the master bathroom to clean ourselves up, while Jason went downstairs to the guest bathroom to clean up and get dressed. After David and I got dressed, we joined Jason in the living room. David put his arm around my waist and reached out his hand out to shake Jason's: "Good for you, Jason!" he congratulated him. "You've done well for your first time. There is much more for you to learn, of course, but for a start... you done great! What do you say, Samantha?"

I wasn't quite sure what to answer, so I blurted out the first thing which came to mind: "You've got a great body," I said, half embarrassed once I heard the words coming out of my mouth.

"And with time," David added, "Samantha and I will mentor you into learning how to master your body so that you can properly pleasure a woman."

Jason sheepishly looked down at his shoes, and said: "Thanks David and Samantha. You guys really are incredible mentors. I truly never expected this level of generosity on your parts, but I am so, so appreciative."

After David and I walked Jason to the door, David gave Jason a hearty pat on the back, and I gave Jason a strong embrace and a peck on the cheek. Our mentorship had broken new ground, and we were now navigating unchartered territory. I was already looking forward to our next session with Jason, and could not wait to discover in which direction David would lead the young boy's education. All I knew was that my body would serve as the educational prop. It was the least that I could do to contribute my part to helping out with the local youth....

(To be continued)