My name is Sam. This happened about five years ago when I was forty-five years old. I met and married a woman who had a six-year-old son named Bill. He was shy around most people but for some reason, we really hit it off. He seemed to like spending time with me more than he did even with his mom. 

We did all kinds of father-son stuff together. I taught him how to ride a bike, how to swim, we camped, sometimes as a family or just me and Bill. 

One time when Bill was sixteen he and I were on a camping trip just the two of us and it was the day we were to head back home when out of the blue he asked if we could stay an extra day.

I told him, “Sure.”

He asked me, “Don’t you want to know why?”

We had been camping for a week. We had a camper, it wasn’t just sleeping bags and a tent. We didn’t like roughing it. We pretty much liked the alone time without my wife, Bill’s mom. I could tell something was bothering Bill from the way he had been acting the week we had been camping.  I didn’t want to pry. I knew he would tell me in his own time. Bill asked me again, “Don’t you want to know why I want to stay another day?”

I told him, “You must have a reason and it must be important to you. If it’s important to you then it’s important to me.”

We were in the camper at the time and he sat down on one of the beds and started to cry. I sat down beside him and asked, “Hey, hey. What’s wrong champ?”

It took him a minute to start speaking again. He said, with his head bowed, “I really need to talk to you about something.”

I told him, “Hey, you can talk to me about anything. You know that.”

Over the years we had had a lot of father/son talks. He said, “Yeah, I know. But this is different. God! I’m so embarrassed!”

I told him, “Just take your time and tell me. And don’t worry about being embarrassed, it’s just us guys here.”

It took him another minute before he started talking again. “It’s about me and Bob.”

Bob was Bill’s best friend. When I started dating Bill’s mom Bob and his mom always seemed to be there when I would come to visit. Bob was two years older than Bill. Since Bill turned sixteen about six months ago he had been spending just about every weekend at Bob’s house.

I asked him, “What about you and Bob?”

He looked up at me with tears in his eyes and said, “You're going to hate me when I tell you.”

I put my arm around his shoulders and said, “Hey I could never hate you, Bill.”

He told me, “I really like Bob.”

At first, I didn’t understand what he was trying to say. I thought maybe Bob and his mom were moving away or maybe they had a fight and weren’t friends anymore. I asked him, “Did something happen between you and Bob, is he moving away or did you two have a fight or something?”

He started to wipe the tears from his eyes with his t-shirt and he said, “No, nothing like that. I mean I really like Bob.”

I didn’t answer at first because it hadn't dawned on me right away what Bill was saying. When I did answer I said, “You mean you like Bob like…”

He said, “Like I’m not supposed to. Like how a boy likes a girl.”

I told him, “There’s nothing wrong with how you're feeling Bill. I mean I think all boys your age go through this. It’s just a part of growing up.”

Bill asked me, “Did you like a boy when you were my age?”

I had fooled around with a few boys when I was Bill’s age. Oral sex mostly. But I lost my virginity to a boy a few years older than me. I have never lied to Bill about anything so I told him, “Well, I did stuff with boys when I was your age, but I didn’t have feelings for a boy. We just did things, experimented.”

I then asked him, “Does Bob know how you feel?”

He said, “Yes. he does.”

I asked, “Does he feel the same about you?”

I could see Bill’s face turn beet red and he said, “Yes he does.”

I told him, “From the way you are blushing I would say it’s safe to say that the two of you have done some experimenting of your own.”

He was really opening up to me now. He said, “Yes, we have sucked each other off and jerked each other off.”

I asked, “And did you like that?”

He said, “Yes. The first time we did stuff I sucked him first. I told him not to cum in my mouth. He promised he wouldn’t but then he did. When he came he shoved his cock down my throat and held it there and told me to swallow it all. I could have pushed him away but I didn’t because I was afraid if I did he would get mad and not want to be friends anymore.”

I told him, “I’m sorry he did that champ.”

He said, “After it was all over I realized I liked it. He then sucked me but he didn’t swallow. He pulled his mouth off and had me give him a facial. Then he had me kiss him and lick my own cum from his face.”

He told me, “You can not tell mom about this.”

I told him, “Hey, your secret is safe with me champ.”

He then told me, “Bill wants to do more.”

I kinda knew what he meant but I asked, “What do you mean, more?”

He said, “You know, sex.”

I told him, “Mmmm, I see. And you don’t want to.”

He said, “It’s not that…it’s just. Well, Bob is so big. I’m just afraid if once we start and I change my mind he might not stop. I mean he promised he wouldn’t cum in my mouth. And he did. I have read stories online about people’s first time having anal sex and they say it hurts really bad.”

I told him, “Well it can hurt bad if you don’t know what you are doing.”

He asked me, “Have you had anal sex?”

I took his mother’s anal virginity and she was really tight and I liked that and I had taken a few guys anal virginity also. Plus I lost my anal virginity when I was about his age. I didn’t lie to him. I told him, “Yes, I have had anal. Giving and receiving. I took your mom’s anal virginity right after we started dating.”

Under the circumstances, I didn’t think his mom would mind me telling him. Then I added, “In fact, your mom and I have anal sex on a regular basis and she loves it. Once your anal cherry gets popped the pain isn’t so bad.”

He told me, “I really want to do it. But I want to do it with someone I trust completely.” 

Then the next thing he said took me completely by surprise. He asked, “Would you do it?”

I tried to talk him out of it. I said, “Bill, you don’t want an old guy like me to be your first. You want it to be with someone you love.”

He said, “You said you just fooled around with guys. Did you love the guy that took your virginity?

Again I was honest with him, “No, I only met him about five minutes before we had sex. But I think your first time should be special, Bill.”

He stood up and said, “It will be, if it’s with you.”

I didn’t know what to say. I would be gentle and stop if he wanted to. If I didn’t do it he might decide to let Bob fuck him instead. I asked him, “You're sure you want to do this?”

Bill told me, “Yes, and if you do it, take my anal virginity. It won't be so bad when Bob fucks me.”

He then started to beg, “Pleeease, say you'll do it.”

I finally gave in, “Ok, but we do it my way.”

He got all excited and gave me a big smile and then tried to kiss me but he stopped and said, “ I'm sorry. I didn't mean…”

I didn't say a word. I put my hand on the back of Bill's head and brought his face to mine and kissed him on the lips. His lips were so soft, just the kind I like. When I broke the kiss Bill said, “You like kissing guys?”

I told him, “I like kissing young guys.”

Bill then asked, “Do you find me attractive?”

I knew I shouldn't, but I did. I asked him, “Are you ok with that?”

He said, “Sure…uh, how do you want to do this?”

I asked him, “Do you trust me?”

He didn't hesitate, he said, “Completely.”

I asked him, “So, you just want to do it, or…?”

He smiled and said, “Pretend I'm mom. Do what you did when you fucked her ass for the first time.”

I gave him a quick kiss on the lips then moved down his neck kissing and licking. As I was doing that I reached down and took the edge of his t-shirt in my hands and slowly lifted it up and over his head and off.

Next, I sat down on the bed. He was standing beside it. I had a T-shirt and swimming trunks on. The same as Bill except now he had his t-shirt off.

I kissed down his neck to his chest and planted a kiss on each of his nipples then sucked on them. As I was doing this I took his hand in mine and put it down the front of my swim trunks. 

I didn't have to speak. He wrapped his hand around my cock and I heard him gasp. I was now kissing and gently biting his earlobe and when I heard him gasp I whispered in Bill's ear, “Are you ok, champ?”

He said, “Y-yes.”

I wasn't convinced so I kissed his lips again and asked,  “Are you sure? I mean we don't have to do this right now.”

He told me, “No…”

I asked him, “What's wrong?”

He again said, “Nothing.”

I told him, “Come on Bill. We don't have any secrets, right?”

He said, “It's just that…you're so big. I thought Bob was big, but you're way bigger.”

I said, “Well, maybe we should stop then.”

But Bill said, “No. I'll tell you if I want to stop.”

I was so aroused, I didn't want to stop either, but if he would have wanted to stop I wouldn't have forced him. 

I told him, “Ok, up on the bed and on your back.”

He did like I told him. He propped himself up on his elbows and looked down at me. I told him, “Lay flat on your back.”

He quickly did as I told him. Then I came up and hovered over him. I kissed him again on the lips, then slowly moved down his neck, kissing, licking, sucking. I kissed down his smooth chest. 

Next, I hooked my thumbs in the waistband of his swim trunks and slowly pulled them down and off. He was now lying on the bed naked. 

His young cock was starting to grow and he wrapped his hand around it and slowly started to jack himself. I lovingly slapped his hand away and said, “I'll do that.”

I told him, “Put your arms at your sides and keep them there.”

Again he did as he was told. I wrapped my hand around his young cock that wasn't quite fully erect yet and slowly jerked him. He closed his eyes and moaned. 

Once he was fully erect,  throbbing in my hand I told him, “Now this won't be exactly like how your mom lost her anal virginity since you don't have a pussy.”

I don't even know if he heard me. He just moaned, “Oh God! That feels so good!”

When I leaned in and touched the tip of his cock with my tongue I thought he was going to shoot his load but he didn't. His cock was about average for a guy his age and build. He was a little over six feet tall and weighed about one hundred and twenty-five pounds. He was kind of lanky. He had long legs. 

When I took the head of his cock into my mouth he put his hands on the back of my head and pushed my mouth onto his cock. I didn't mind, I could have stopped him, if I had wanted to. When I slowly started to bob my head up and down on his cock he kept his hands on my head and just moaned. 

I could tell he wasn't going to last long. I heard him say, “Oh God, oh God! I'm  going to cum!”

That's when I started sucking faster and I started to caress his balls with my hand. It had been so long since I had tasted a guy's cum, almost thirty years and I wanted Bill's. It wasn't long after I started playing with his balls that I felt him shooting his load down my throat. 

I took his cock balls deep so I didn't lose a drop. It tasted as good as I knew it would. As soon as Bill finished shooting his load I got up and leaned over him and kissed him, giving him some of his own cum in his mouth as we kissed. He wrapped his arms around my neck and pulled me close to him as we kissed.

I broke the kiss then quickly got undressed. I was on my knees on the bed and I told Bill, “I think you need to return the favor, don't you?”

He smiled and got on his knees in front of me, wrapped his hand around my cock, and slowly jerked me. He licked my pee slit with his tongue then looked up at me and said, “I don't think I can take it all, it's just so big.”

I told him, “Just take what you can.”

He stroked me about half a dozen times slowly as he sucked on about half my shaft. Then with my cock in his mouth he moved a hand to each of my thighs and took more of my cock into his mouth and down his throat. He couldn't get much more than half my cock down his throat.

He made himself choke and gag then came up for air and said, “I can't take it all.”

I told him, “Hey, nobody said you had to take it all.”

He said, “I know.  But I want to. Will you help me?”

I told him, “Sure Bill, if you want.”

He didn't answer me. He just put his hands back on my thighs and took my cock down his throat until he started to gag and choke and then I put both my hands on the back of his head and shoved my cock down his throat until my balls were resting on his chin. 

He looked up at me and I could tell he was smiling. He looked like he was going to be sick. I asked him, “Is that enough?”

He didn't respond. I could feel his tight throat around my cock and it felt great. When he tapped my thighs with both his hands I took that as a sign that he wanted me to let up so I did. He didn't pull his mouth off my cock. Instead, he started to suck it in long slow strokes. He never took my cock out of his mouth completely. 

He gradually sped up. He sucked me faster but with shorter strokes. Just taking what he could handle without gagging and choking. I moved my hand back to his bare ass and squeezed it. He didn't object to that so I spread his cheeks and gently probed around his tight virgin hole with my finger. I was really going to enjoy fucking him. I told him, “Oh God, Bill! You keep sucking like that and I’m going to cum!”

I’m sure he heard me but he just kept right on sucking. When I started to cum he took my hand and placed it on the back of his head. I assumed he wanted me to “help” him take my cock balls deep so when I started to cum I shoved his mouth all the way down onto my cock until my balls were resting on his chin. 

I held him there until I emptied my balls down his throat. After I was done emptying my balls, Bill pulled his mouth off my cock and laid face down on the bed.

I placed my body over his, propped myself up on my arms and started kissing his shoulders. He said, “Mmmm, I like that.”

I didn't answer him. I just moved down his body, placing kisses as I went. When I got to his ass I planted a kiss on each of his cheeks. I gave his ass a love slap with my hand and said, “Spread those cheeks for me like a good boy.”

Bill reached back and spread his cheeks for me like I told him. I licked his cheeks with my tongue. He told me, “Mmmm, that feels so good.”

I probed around his hole again with my finger but I didn't penetrate him. I asked him, “Tell me, Bill. Have you ever put anything in your ass before? Fingers, toys, anything?”

He shook his head and said no. I really wanted to fuck his ass because I knew he would be tight. I told him, “You know it's going to hurt when I fuck you, right?”

He said, “Y-yes.”

I said, “Are you sure you want to do this?”

Bill said, “Y-yes. I'm sure.”

I could have used my finger on him to loosen him up a bit. But I was too selfish. If I loosened him up with my finger it wouldn't be as tight and as pleasurable for me and it had been a long time since I fucked a tight ass.

I did get some lube to fuck him with. I got up off the bed and got a jar of Vaseline I kept in a gym bag for when me and the wife used the camper for a night of lovemaking.  

Bill kept his eyes on me as I dug through the bag for the Vaseline. He asked me,  “What are you doing?”

I kept looking through the bag and I told him,  “Just getting some lube for us,  that's all.”

Once I had the jar I went back to the bed and got behind him again. I got two pillows from the head of the bed and placed them under Bill so his ass was up off the bed. Next, I got a generous amount of Vaseline in my hand and lubed up my cock. 

I told Bill, “Reach back and spread your cheeks for me again.”

He did and he asked, “Aren't you going to lube me up? Whenever Bob and I watch porn and it's someone's first time doing anal they lube up their whole real good.”

I know I shouldn't have lied to him but I said, “Well,  that's in the movies. And this is real life.”

I then asked, “Are you ready, Bill?”

Again he just nodded his head. Since Bill had his ass cheeks spread I had easy access. I gently touched his virgin hole with the tip of my cock. I heard him gasp. I tried to be gentle as I entered him but he was just too tight. I put my hand on his hips and with one quick hard thrust, I forced just the head of my cock into his virgin hole. 

I could hear him trying to stifle his screams from the pain. I told him, “Go ahead and scream. It's not good to hold it in. It's just the two of us here. Nobody will hear you but me.”

As I slowly slid my cock into his virgin asshole he tried not to scream but the pain just got to be too much. He let go of his ass cheeks and started to pound his fists into the bed mattress. My cock was about halfway in at this point. I gave him a minute to get used to my cock being in his ass. I leaned forward and whispered in his ear, “Are you ok, do you want me to stop?”

Tears were running down his face. He told me, “No, didn't stop! I need  to do this!”

I didn't say a word and then slowly without stopping I slid the rest of my cock into his virgin ass all the way up to my balls. As soon as I started pushing in again Billy buried his face in the pillow that was still on the bed up by his head. I could still hear his cries through the pillow. 

I didn't ask him if he wanted me to stop because I was afraid he would say he did and to tell the truth I didn't know if I could if he wanted me to. Once I was all the way in him balls deep I shushed him, “Shh, shh. It's ok, the worst is over. I'm just going to leave it so you can get used to it, ok?”

He turned his face to look at me and smiled. He asked me, “Was mom this tight?”

I told him, “Yes, and she bawled like a baby. Unlike you, she cried like a baby.”

He said, “But didn't she want you to fuck her ass?”

I told him, “Yes, she did. She wanted me to fuck her in all her holes. It didn't take her long before she started to enjoy my cock in her ass. In fact, she prefers anal now when we make love.”

I asked him, “So, you want to keep going?”

He gave me another smile and said just one word, “Yes.”

He turned his head so he was facing forward towards the head of the bed. I slowly pulled my cock from Bill's asshole. I heard a deep sigh of relief come from him as I did. I put it back in slow but faster than the first time, again going in without stopping until I was balls deep. 

As I said my cock into him I saw him ball the sheet from the bed in his fists. This time I only left my cock in his ass for a few seconds before pulling out. He had his face buried in the pillow again to try and stifle his cries. I was about to pull my cock out of his ass but before I did I asked him, “Are you ok? We can stop anytime you want. Just say the word.”

He kept his face buried in the pillow and he furiously shook his head from side to side indicating he didn't want to stop. I pulled out of him then shoved my cock back in faster. This time I didn't wait once I was balls deep. As soon as I felt my hand touch his ass I pulled my cock out then shoved it back in faster and harder. It wasn't long before Bill started to enjoy it. 

He turned his face to the side of the pillow and said, “Oh my God! That feels so good!”

He reached back and grabbed his ass cheeks and spread them, like he thought I could get my cock in him deeper if he did. But I was going as deep as I could. I smiled and said, “You like that, don’t you, Billy”

He didn't look at me. He had his eyes closed, but he had a big smile on his face and he pretty much screamed, “Yes, I do! Fuck me faster, harder!”

I was happy to oblige. When I was getting close to blowing my load I asked him, “Do you want me to fill you up or cum in your hole?”

He still had his eyes closed and asked, “Shouldn't a guy be filled up when he loses his anal virginity?”

I told him, “You're right. It was a stupid question.”

I fucked him as hard and as fast as I could and I was soon cumming and filling his hole with my load. Once I emptied my bags in Bill's asshole I told him, “Turn around and clean my cock.”

He didn't hesitate. He tried to turn around but the pain from me fucking his ass was too much. He could barely move. I helped him turn over into his back and I told him, “That's ok, we can do it like this.”

He was now flat on his back and I slowly lowered the head of my cum covered cock to his mouth and slid it into his mouth and down his throat. I loved how Bill's throat bulged as I slid my cock in and out of his mouth. I couldn't believe how well he sucked cock. 

Once he had cleaned my cock and balls off my cum I pulled my cock from his mouth and lasted down beside him on the bed and asked him, “So, you want to return the favor?”

Bill got a confused look on his face and asked, “What do you mean?”

I said, “Do you want to fuck me now?”

Bill had a nice size cock and it would have felt good to be fucked with it but I want to try and force him. I told him, “No. Not if you don't want to.”

He then asked, “You're not mad that I don't want to. I just thought maybe you would, that's all.”

He told me, “I guess I'm just more of a submissive.”

We were laying side by side and I positioned him with his back to me then I pulled him into me. I spit in my hand and then wrapped it around his hard that was leaking precum and slowly jerked him. 

He didn't object to that, he just moaned. He moaned louder and faster as I jerked him faster. Just before he shot his load he was moaning, “Mmmm, yes! Faster Daddy, faster!”

He had never called me daddy before or even Dad. It was always Sam. I never tried to make him call me dad, I didn't want it to affect our relationship.

Once Bill came from me jerking him I brought my hand up to his mouth and told him, “Lick daddy's hand clean like a good boy, Billy.”

He quickly did as I told him, licking, then sucking on all my fingers. When he was done he turned around so we were facing each other and asked me, “Did your little boy do a good job, Daddy?”

I kissed him and said, “My little boy did a great job.”

We fell asleep like that.

More to come maybe. I haven't decided yet. Hope you liked it.