Anal Sex Ch. 04

Story Info
Anal sex with a 19-year-old guy.
1.1k words
3.89
78.2k
4
1

Part 2 of the 3 part series

Updated 09/22/2022
Created 11/27/2003
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I have been doing this anal sex, since 1985 but the best anal sex I did was in 1997 with a very cute young teenage boy of about 19 years of age. He became my friend while I was coming to my hometown by air from some other city. He was a very shy person and never had any sexual experience except playing with him self. Since we had become good friends, so we were frequently visiting each other's place. One day he was at my place and we indulged in sexual discussion about the sizes and colors of dicks. He told me that he had a six-inch dick and I was amazed.

I told him to show me, but he refused .I took it as a chance to have sex with him, so I removed my lower part of dress to my knees, exposing my dick to him. My dick was semi erect at that time and is of about six and a half inch length. I asked him to see it carefully and compare it with his own. I went more close to him and placed his hand on my dick. He grabbed my cock and I told him to play with it. His pumping made me rock hard very soon. In the mean while I pushed my hand towards his dick, which was in the pants. I opened his zippers and pushed my hand in.

I was astonished to feel that he was not putting on an underwear .I held his cock in my hand and took it out. I found his cock semi hard and started pumping it. Soon he was hard as well but his dick was about four and a half inches long. I offered him to come to the bed so that we can play there. We came to the bed where I removed his jeans and mine lower part of dress completely. I started licking his cock and than started sucking it. His cock was shaved but his balls and anus had pubic hairs. He was amazed with the pleasure he was getting .I forgot to tell we both have circumcised cocks.

Soon his movements went out of control and at that time I told him to pull out before ejaculation, but he could not do so and unloaded his sperms in my mouth. I kept sucking his cock and drank all sperms, he had sweet taste. After that I got up and did french kissing with him and then introduced my dick to his lips. He was bit shy in sucking, so I came right up to his face and pushed my cock in and started fucking his mouth. After some time I came in his mouth but never withdrew till the time he had sucked even last drop of my cum.

We then had some rest on the bed and removed the remaining parts of our dresses and became complete naked. I turned him over on his tummy and came right on his thighs and started kissing his back. Soon I shifted my attention towards his soft butts and started kissing and licking them. After some time I parted his butts and licked his anus. This anal licking continued for some time and he enjoyed it a lot, as it was a new experience for him. Soon I was pushing my tongue deep in his anus and this made his cock go hard again, and this was a good sign.

I then told him to lick my anus, which he did and was excited to see my hairless anus and also asked me how to shave the anal area. We then changed our positions to sixty-nine and started sucking each other. When I found that he was hard enough, I asked him to fuck my ass. I positioned my self on all fours, and told him to come behind him. He came behind me and parted my hips. I gave him oil to apply on my anus and his cock. He did it and then tried to mount my ass. Since he had no experience so he was not able to push his dick in my ass and it slipped.

I grabbed his dick with my hand and pushed the head past my anal ring, rest of the dick went in easily. I told him to start moving in and out and jus after few strokes he came in my ass. It was something new for him to come in side the ass and he remained motionless for some time with his dick still in my ass. After some time his dick got soft and it slipped out. I gave him tissue paper to clean my anus and he did it.

I then told him to bend over on the bed in doggy style so that I can fuck him now. He did as told and I came behind him. Parted his hips and started licking his ass. Soon I was pushing my tongue deep in his anus. With other hand I was pumping my cock, which by now had become rock hard again .I told him to lower the upper portion of his body and raise his ass. Now his tight ass was in line with my cock. I applied a lot of oil on his anus and pushed my index finger in.

I started finger fucking his ass and soon I was pushing two fingers in his anus. After this I introduced my well-lubricated dick to his anus. But as soon as I tried to push head of my dick in his anus, he jerked due to the pain and my dick slipped out. I told he to part his buts with his hands and be relaxed. With my right hand I pressed his back downwards so that his movement should be restricted. With my left hand I again pressed my dick against his anus . With a little effort I pushed the head of my cock in his anus, this stretching of anal ring was too painful for him. He begged me to stop and pull out but I did not pay any attention to what he said and pushed my complete dick in his anus. His small anus was too tight for me to move my dick, so I decided to remain motionless for some time so that his anal ring can relax.

Soon his anal ring was relaxed and after remaining in this position for 3 to 4 minutes I started moving my dick in and out and came in his ass after about ten strokes. Fucking a young tight virgin anus was a unique experience and I enjoyed it to the maximum limits. We both became good friends since than and started having sex regularly. His pain was also over after few fucks and he started loving dicks up his anus for longer duration. We both are lovers for past few years and we both love our status of being in love with each other.

Well that's the end of chapter four. See you soon in chapter five.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
1 Comments
AnonymousAnonymousalmost 17 years ago
great time

i caught my room mate reading this story on my laptop i asked him if he would like me to come up his ass to my surprise he said yes it was my first time and super

Share this Story

READ MORE OF THIS SERIES

Similar Stories

I Got Myself a Cum Slut Pt. 01 Bi Curious married man experiments.in Gay Male
A Matter Of Size A straight guy discovers the big penis of the gym couch.in Gay Male
Gay Sex for Gregory A shy young man rapidly learns and adapts to gay sex.in Gay Male
Fill in Girlfriend Max fills in for his coach's girlfriend.in Gay Male
Getting Ass-Fucked in my Ex-Wife's Bed Ex-wife is out of town; I ride a beautiful cock in her bed.in Gay Male
More Stories