Experimenting with Cock Ch. 03

Story Info
In our second meeting Josh takes my anal virginity.
1.8k words
4.44
99.3k
16

Part 3 of the 5 part series

Updated 10/28/2022
Created 05/15/2010
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abiguy
abiguy
173 Followers

Thanks again for all the comments. The more feedback I get the quicker I'll get stories out ;) And again my stories are all true :)

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Part 3:

Later that night I got a chance to talk to Lauren and tell her about my experience with Josh. We both got on cam and I started to tell her in detail what happened. Her mouth was open from almost the beginning. Her top was off by the time Josh had his pants down in my story. By the end we were both naked and she had came twice. It was so exciting to tell another person such an erotic moment. A moment I wanted to keep secret from others I knew.

She looked great as she masturbated to hearing about me sucking cock. She was 3 years older than me making her 25 but she didn't look it. She looked like a fresh 18 year old. Her soft round breasts jiggled as she fucked her wet shaven pussy with her blue vibrator. I wanted to fuck her almost as much as I wanted Josh to fuck me. She was laying on her back with her legs in the air exposing her pussy and ass to me as she came a third time. That's how our cam sessions usually went but we didn't masturbate to something this exciting in a while.

After she was done I texted her the pic of Josh's cock (to show off my new play thing) I also told her that he wanted to fuck my ass next time. This made Lauren almost as excited as the first time I told her that I liked cock. She gave me some pointers that helped her with her first time doing anal. She begged to be able to watch next time Josh and me hooked up. I agreed of course.

By that time Josh was available again and we were texting each other for a while. He was telling me how much he liked our encounter and couldn't wait for the next night to come. I agreed and told him that I was interested in him fucking me. He was glad I had taken his offer. He told me not to worry about a thing, that he had broken in a few boys and he would be gentle with me. We ended up sexting and swapping a few pics before I blew my load a second time that night.

A day had passed and it was almost time for Josh and I to meet again. I couldn't wait to see what he had in store for me. My cock was hard practically all day. He had texted me directions straight to his house this time instead of meeting up first. I arrived at his house right on time, almost shaking from excitement. Josh answered the door and we hugged and he went for a light kiss and I replied with my tongue in his mouth.

"Well hello there" he smirked, inviting me to come and sit down.

We had a beer as I told him about Lauren wanting to watch us. I told him the relationship Lauren and I had and he had no problem letting her watch. We hopped on his laptop and connected to Yahoo but unfortunately Lauren wasn't online. Disappointed, we decided to find some porn. We found one of a boy about 19-20 being fucked by a man around 30.

"He's got a nice twink there" Josh said, his eyes locked to the screen.

Not knowing what twink meant exactly I asked him. He explained it was a young boy who was slender and loved cock.

"So I'm your twink?" I exclaimed.

"Fuck yeah you are" He laughed, giving me that almost evil smile again.

Josh was only 2 years older than me but looked and acted 10 years older. Being submissive to an older man was the hottest thing I could imagine and Josh was fulfilling my fantasy. Deciding that Lauren wasn't going to show up Josh suggested moving to the bedroom. I left Lauren a message (Hey i'm at joshs were about to fuck! where are u??) then followed Josh to his bedroom.

I was only a minute behind Josh but by the time I walked in he was naked with his legs spread on the bed. My mouth started to water as soon as I saw his cock, still big only being half hard, and his hairless balls just laying there on display for me.

"Come on twink, get naked" he said in a seductive voice.

This was first of many times he would call me twink, and I loved it already. I did as he asked and stripped right where I was standing and slid onto the bed right into his crotch. Resting my cheek on this inner thigh, I started to suck on his left ball then had both in my mouth. Grabbing his shaft I jerked it to full hardness then licked to the top and started bobbing my head on his massive organ.

"Stop...stop" Josh moaned softly.

I stared up at him, the head of his cock still in my mouth.

Looking down at me he said, "Don't make me cum yet Bry I want to fuck you."

My ass clinched at the thought. I wanted this so bad but was I ready? Either way it looked like I was going to get fucked tonight.

Popping the head out of my mouthI shyly asked "n..now?".

Walking naked over to the dresser he replied, "Yes now, why? are you scared little twink?" He joked as he looked through his draw for a box of condoms and lube.

Josh was only joking but being talked to so dominantly really turned me on. I tried to play it off.

"oh but I wanted to suck your cock some more" I grinned.

"If you sucked me much longer my cum would be all over your face again" He laughed.

My cock jerked at the thought of having cum on my face a second time.

He walked back over to the bed rolling a condom down his rock hard cock and holding a bottle of lube.

"Get on your back" he said dominantly but also in a gentle way.

I timidly rolled over in the middle of the bed.

"No, over here silly" he giggled as he grabbed my ankles and pulled me toward him. My ass was now at the edge of the bed and he still had my legs lifted. I felt so vulnerable but safe knowing Josh was in control. He spread my legs, almost the same as Lauren was spread the night before I thought. He lubed up his cock and spread some on my hole. I'll never forget looking up at him as I lay on my back, my legs in the air while he lubed his enormous cock and showed off his toned body.

"Are you ready?" he asked with a big smile.

"Yes" I moaned salivating over his body in my vulnerable position.

He placed the head against my hole. It was a strange feeling but also felt really good and it wasn't even in yet!. I remembered what Lauren told me and tried not to tighten up and keep my hole loose. With a grunt he popped the head of his cock inside me.

"How does that feel" he asked softly

"It feels amazing" I moaned, my eyes now shut.

"Get ready, here comes some more," He moaned.

I braced myself as he pushed in at least another inch. I was moaning softly and Josh could tell I was enjoying it. He went a little deeper before pulling out and then going back in. He started to fuck me very slowly. I was in heaven.

"Your taking my cock good Bry," He whispered in between strokes.

He got his cock about half way in before it started to hurt. I whimpered and he pulled back not going any further but fucking me a bit faster now. I was moaning and grunting like mad. I grabbed my own cock and began to jerk it.

"I'm going to cum Bry," He moaned, fucking my hole faster now.

All I could do was moan back then I suddenly felt his cock spasm and the cum start to pump out. It was an intense feeling. I started to jerk faster and moan louder. I could feel his cock finish pumping cum into the condom. My head was back and my eyes closed as I jerked my cock with my legs spread. That was until I felt Josh grab my wrists and pin them to the bed.

Josh had pulled his cock out of my ass and leaned over me to take my hands away from my cock. My eyes quickly opened to see what was happening and why it was happening.

"Don't cum yet, I want you to fuck me." He moaned seductively looking down at my helpless body.

My hips gyrated into the bed and my cock jerked uncontrollably having almost reached orgasm. I was shocked he asked me but also very eager, really needing to bust a nut at this point. I stood up as he handed me a condom. Taking my place at the end of the bed Josh got into a doggy style position.

"Do you want me to go slow Josh?" I asked not waning to assume he could take a pounding.

"I like it hard and fast" he said, turning his head around to wink at me.

I earnestly grabbed the bottle of lube and spread it on my cock and got positioned behind him. I have fucked my fair share of girls in this position but seeing a big hanging cock instead of a wet pussy made me want to sink my cock in even more.

I started to push my cock into his hole and started to give it to him like he wanted "hard and fast". Grabbing his waist I was going balls deep wanting to bust my nut so bad. He was moaning and cursing into the mattress as I unloaded my balls into the condom.

"Fuck!" I moaned, achieving the best orgasm I had up till that point.

After giving him a few more pumps I pulled out and threw the condom in the nearby trash.

"Fuck that was great, next time I'm getting fucked first," He moaned as rolled over to watch me join him.

"Fuck, your amazing! I never came so good in my life" I said now joining him naked on the bed.

Our naked bodies touching as we laid there exhausted from all the activity. Josh kissed my lips before getting up and offering me a beer. "Yes, please!" I said as he left the room.

_________________________________________

Part 4 coming soon! The night isn't over yet and Lauren finally gets online!

Thanks to all the people sending feedback and comments keep them coming!

abiguy
abiguy
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AnonymousAnonymousover 2 years ago

I am a butt virgin myself. I like how you were telling about your first experiance. I heard it's a little painful but it feels good. I never had sex (except oral when drunk). I have put carrots, and other things, up there. I even went so far as to get some KY from the grocery store to help. Several evenings I would read erotic srories, put some KY on a carrot and stick it up my naked ass while my eyes were closed and I imagined it was a dick. It was awkward, but I tried to stroke myself while a shoves tlat peeled carrot up myself. It felt great as my butt clenched around it as I came. I never got up the nerve to actually pick up a guy at a gay bar or anything.

AnonymousAnonymousalmost 10 years ago
Love it!

My first bisexual encounter was when I woke up in the middle of the night with a buddy sucking my cock. It was incredible! He was enthusiastic and doing his best to make me cum. After that, I let him suck my cock whenever we were together!

This was back in the '70's when HIV was not heard of, we were young and experimenting. One day I had walked to his house because his parents were gone and as soon as I walked in, horny as could be, he was on his knees pulling my cock out as usual, sucking not just to suck my cock, but to earn my cum. That boy loved the taste of cock but lived for the taste of what I found out years later, MY cum!

So that day he had sucked the cum out of me within 60 seconds and stayed on his knees with my cock resting in his mouth until I started to firm up again. This time he got me hard and close to cumming when he stopped and asked if he could fuck my ass. I was shocked and initially said no, but he kept after me promising he'd give me a handjob while he was fucking me.

After a bit of thought while he played with my cock, I agreed. I bent over the back of his couch while he greased me up with cooking oil (we were young!) and then his cock. Surprisingly, I was able to relax and when he popped that huge head through my sphincter muscle, my ass clamped down and he wouldn't have been able to pull it out! There was little pain and he soon had it buried to his nuts and held still for a little bit. He reached around and started jacking my cock before he started the in and out action and my nuts emptied instantly! I couldn't believe the feeling. My cumming set off his own orgasm without even stroking in and out and I can still remember feeling his cum filling my ass. He was so horny that as soon as he was done and pulled out, dropped to his knees and sucked and cleaned me up. From then on, we sucked and I let him fuck me though I never fucked him. I just found the idea repugnant. We never kissed or touched, we weren't gay and neither of us found any pleasure in that. Instead, we merely sucked one another and he would occasionally fuck me though I preferred to suck his cock most of the time.

Fast forward 5 years during which time, we made sure each others nuts were emptied, we both married our wives and as soon as we were married, that was it, no more playing. Within 5 years he was divorced and started hanging out around our house. I'd confessed to my wife about how we used to play and it made her hot. After a night of drinking, she talked us into doing it in front of her. He dropped to his knees and while she watched, sucked the cum out of me in less than a minute! She was amazed at how quick I popped in his mouth and how much he obviously enjoyed the taste, unlike her. I sucked him and showed her my cocksucking prowess, swallowing every drop like a pro. She masturbated in front of us while watching, helping both of our orgasms!

The next day when we all woke up, he and I very embarrassed, my wife wanted more. So later on in the morning, with her having a chance to watch him spend a few hours nursing on my cockhead and emptying my balls twice, she wanted to see him fuck me and promised to suck my now sore cock while he did it. It didn't work out as well as I hoped, she spent most of her time behind me with my cock in her hand so she could see his cock running in and out of my asshole. I think SHE came when he started blowing his nuts into my ass. It was all so nasty, his cum leaked out of my ass for hours! This was something we ended up doing on a fairly frequent basis, until he remarried a decade later. The funny thing is, he never fucked my wife. Even though she was a high school horny slut as soon as we married, she never looked at another man and 40 years later, has never fucked another man though I brought it up more than once with her shooting me down every time.

We missed our times with our friend. He wouldn't play with us anymore until his wife died tragically some 30 years later. Then sitting in our living room one afternoon, my wife walked out of our bedroom wearing just a nighty, stopped in front of him and pulled it up so he could see her pussy. Then she stood right there and masturbated in front of him to orgasm, nearly collapsing on him! After a few minutes of rest, she stood back up and started masturbating again, this time I fished his cock out and started sucking his bone which was hard as a rock! Only a few seconds and I was rewarded with a HUGE mouthful of cum. He still hasn't fucked my wife, I don't believe they ever will.

AnonymousAnonymousabout 13 years ago

Loved the story. I love being on my back with my ankles on his shoulders, watching him watching me, as he slowly fucks my ass...mmmm

UndeadloveUndeadloveover 13 years ago

I'm loving this story! It just turns me on they are really great!!!;)

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