Dirty Confessions - Reveal your innermost secrets.

#2787

Submitted:

""

Jerry had been my best friend for a number of years. Then he moved away. I thought my wife had a little crush on him at times. A few years later I read on Facebook that he had come out as gay. At first I was pretty shocked bu came to realize he was always gay, he just didn't come out until then. I thought about him quite a bit over the next few years and wondered about his experiences as a gay man. Sometimes I even jerked off thinking about his cock.

A few years ago he came back to visit some friends. We went out to dinner and chatted about life and things. Then I asked if I could inquire about his life as a gay man. He was open to it and I found out all about his coming out and what not. We had shared a couple bottles of wine and when he said he probably get back to his hotel room I asked if he could teach me. He looked sideways and I said I wanted to see what he found exciting about being gay. He asked what I wanted to do. I said I wanted him to treat me like he would any other man he met at a bar. He said it will be a whole new experience but if I was willing he would show me. We headed to his room.

He was a bit taller than me and had a large belly. As soon as his door closed he pulled me in and kissed me. Our tongues explored each other for a couple of minutes and he unbuttoned my shirt and was rubbing his hands gently over my nipples. My nipples got hard and so did my cock. Then he said to get undressed. We both took off our clothes and I looked down at his cock. It was a little bigger than my six inches and my cock was almost hard already. He had me lay on the bed and got between my legs. He proceeded to suck me until I was rock hard. Then he took his mouth off of my cock and mounted me in a 69. He put his cock up to my lips and I opened my mouth for him I sucked him until he was hard. Then he asked if I was serious about him doing to me what he really liked. I told him I was and he had me roll over onto my stomach. He proceeded to tie my hands and feet to the corners of the bed lets. I was spread eagle on my belly and wondered what he was going to do. He started by licking my asshole. My wife never even touched my asshole let alone was willing to lick it. This turned me on even more. At the same time he was massaging my ass cheeks and lower back.

I told him this felt really great and he started to slap my ass. At first it was light but after a couple of minutes he was slapping me until it stung. Then he said he really liked his bitch to be crying by the time he would fuck the guy. Then he started to slap me really hard while caressing my balls. It started to hurt and I told him that it was enough. He didn't stop. Pretty soon I was begging him to stop. My ass was on fire. He kept going and a couple minutes later the tears started. I hadn't cried in years but this pain was unbearable. Soon I was wailing and begging him to stop. He said my ass was as red as a lobster. He stopped slapping my ass cheeks and shoved a wet finger into my asshole. What a fucking feeling. It was almost soothing with him gently rubbing my ass with one hand and finger fucking me with the other. I was still sobbing from the pain when I felt him hover over me and put his cock up to my asshole. I couldn't close my legs, but really didn't want to. His cock worked its way into my ass and he started to fuck me. I couldn't stop him even if I wanted to. He laid on top of me and reached under me to play with my nipples, all the while telling me how tight my man=cunt was. I had just about stopped sobbing when he said he was cumming. I felt his warm jizz as he filled my ass.

After he was spent he pulled his cock out of my ass and immediately pushed three fingers in. It was almost like him fucking me again. Then he put his fourth finger in. Four fingers was bigger than his cock and I was being stretched out. One finger was rubbing my prostate each time he pushed in and I felt myself cumming. I was gyrating a bit so he knew I was cumming. He grabbed my nuts to help me empty my balls.After we both had cum he just collapsed on top of me. I told him it felt really great to get fucked by him and sort of wished I was single. He untied me and said to roll over. I did and he straddled my chest. He stuck his cock into my mouth and said to suck him. I did and worked his cock until it was hard. I couldn't get all of it quite in my mouth but he seemed to enjoy it. I sucked him for about 15 minutes and he finally got hard again. He said he was gonna cum in my mouth. Before I knew it he started cumming. I had tasted my own cum once or twice but this was a new experience. He didn't have a large amount of cum but I got enough to taste it and swallow it all. He finally got off of me and we cuddled for a few minutes.

He asked if I liked his cock in my mouth. I did. Then he asked if I liked his cock in my ass. I did. After a bit he said he was going to help me out. I said sure and before I knew it he had grabbed his phone and texted someone. Then he said he had previously spoken to my wife and they discussed whether or not I had gay tendencies. I thought I would be fucking pissed if she ever even brought up the subject but he said she was cool with it and showed me the text. It said "Linda, this is Jerry. I just fucked Tom in the ass and he deep throated me until I filled his gullet with my cum. He loved it!" I couldn't believe he did that but he assured me that it was what Linda actually wanted to know. Then he said we should go to my house and see her.

It was the most uncomfortable I'd been in my 47 years but as soon as we walked in she hugged me and gave me a big kiss. We ended up talking about it for the next three hours and then she said she wanted to see me get fucked. As soon as she said that Jerry took his pants off and told me to suck his cock. I looked at her and her hand was between her legs rubbing her cock through her jeans. She said to go ahead so I took his cock in my mouth and sucked him hard. Then she said she wanted him to fuck me. I was still a little drunk from all the beer the three of us had drank in the last three hours so I stripped and got on all fours leaning over the couch. He proceeded to fuck me for the next 20 minutes. She was now naked with three fingers in her own cunt and I could tell she had cum a couple of times already. When Jerry said he was gonna cum she quickly knelt down beside us and watched him unload inside me. When he finally pulled out his cum oozed out of my asshole.

It was one of the greatest fucking weeks of my life and she had me suck him and let him fuck me every night he was in town. He finally left and we joined a swingers group. I have been fucked so many times in the last three years I thing my asshole is permanently opened. She even uses a strap-on to fuck me on those nights we don't feel like going out. I have become a true cum slut. The biggest surprise of all though was last week when she brought out a bra and one of her dresses and told me to put them on. I was apprehensive but excited at the same time. When I asked her why she said not only was I her bitch I was going to become a fucking tranny as well.

So it goes...

Loading