My Friends

Story Info
Strange trip with male friend, then his wife.
13.3k words
4.55
78.8k
6
0
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
Andy5v
Andy5v
380 Followers

Sometimes life presents us with very interesting situation. Many non-Gay males have experiences with another males in their life. This is what happened to me. The setting begins at my friend's camp located on a river that flows into the Gulf of Mexico.

My friend, Tom and I sat leisurely on the deck of his camp drinking beer. His camp overlooked a slow moving river and it was very relaxing sitting on his dock watching the water flow.

"You know this is really nice," Tom said.

"Yeah, it is really nice just sitting here doing nothing," I responded.

"Yeah, it kind of reminds me of another trip we took. Do you remember that time we hiked up in the mountains?" Tom asked.

"Sure, it must have been at least 15 years ago since we made that trip to Colorado," I answered. I then remembered with a bit of a shock it had been a very strange trip. I had not thought about for years.

"I had a lot of fun back then," Tom said. "We'd better go inside, it's getting dark and the mosquitoes are beginning to attack."

We went inside his trailer and ate a couple of hamburgers.

"I picked up a couple of porno movies. I was going to watch them with Trish but let's take a look at them," Tom said. Trish was Tom's wife. She had remained at home to let the boys go to the camp.

"Ok, sure," I replied. At this time in my life I had just finalized my divorce. It had not been fun. She had told me she was in love with another man and that was it. I had no clue. Tom realized what a difficult time it had been and invited me to his camp so I could get away from everything. It had not been a good year for me and this was nice diversion. At this point I did not realize what a diversion it was going to be. I soon forgot about all my problems.

I thought it was a bit odd for Tom to mention our trip to the mountains. The trip had begun during a time we were both having some major turning points in our life. We both enjoyed the hike up the mountain but the strange part did not begin until we were sitting in our small tent high in the mountain. Tom brought a flash and we began drinking bourbon. We began to talk about old times. Tom told me about some of his early sexual experiences and this is when I told Tom about an incident that I had always kept to myself.

"What happened? You can tell me. It will stay right here," Tom said after I had given him some hints and indicated my embarrassment about the situation. He wanted to know more and now I had said too much to stop. The booze was also loosening my lips.

"It was that time we were going to spend the night in our clubhouse and everyone had something to do except for Doug and me," I began.

Tom's eyes indicated he was very interested hearing more.

"We decided we would go ahead, just the two of us. Everything was pretty normal until we began playing cards. For some reason I suggested we play strip poker."

"Just you and Doug playing strip poker," Tom interjected.

"Yeah, you go the picture. You should you want to hear this," I said beginning to feel embarrassed again.

"You can't stop now," Tom said.

"Before long I was naked and Doug was in his underwear. It was then I got the idea to take off his underwear. This lead to a wrestling match. I managed to pull his shorts down and there we were wrestling in the nude. You sure you want to hear this, Tom. If you ever tell anyone I will get you," I said feeling a bit insecure about revealing this secret from my past.

"Hey, that was a long time ago. And no, I'm not going to tell anyone," he said.

"We soon both had erections and found ourselves rubbing our bodies against each other. I could feel my cock rubbing against his as it was trapped between our stomachs. As we began to rock back and forth on each other it was only a matter of time before I felt a buildup of tension and my cock began to spurt cum. No sooner than this happened, I felt Doug's body tense and his cock twitched and shot cum. We now lay on each other with cum all over our stomachs and chest."

"Wow, that is some story. Did you like it?" Tom inquired.

"Yeah, it really felt good but I'm did not want to think I was gay yet here I found myself on top of another guy. After we cleaned ourselves a bit we talk for a while and then finally went to sleep," I explained.

Tom just looked at me as he took another sip of bourbon.

"You ever sucked a guy's dick," he suddenly asked.

"Well yeah," I stammered. "Just once, it was also with Doug," I replied and looked away.

"Don't worry about it. We are high up in the mountain and if you can't trust me who can you trust. I never sucked a dick, but I have to admit something to you, your story has gotten my dick hard," Tom said. I could not believe it as he pulled down his shorts to reveal his hard cock. I watched as he sat there stroking it. As I watched him stroke I noticed my cock was swelling up in my briefs.

"I guess I can also tell you my cock is hard," I replied and shyly pulled down my shorts. Tom watched as my dick pop out pointing at him.

We just sat there for a moment looking at one another's hard cocks. Then whether it was the booze or everything that was happening in my life at the time, I felt a sudden desire to suck his cock. I attempted to push it from my mind but the more I tried the stronger the temptation became. I did not know what Tom would do if I told him. We were sitting in a small tent at the time and there was very little room between us. I could believe what I doing as I leaned over and grabbed his cock with my hand. Tom offered no resistance. The only other time I had held another man's cock was with Doug. However, the feel of his cock in my hand seemed to be hazing my mind with desire.

I began to slowly rub his cock with my hand. His smile encouraged me. Suddenly I leaned forward and Tom moaned loudly as I slipped his cock through my lips and licked the purple head. He was surprised as I was. There was already some precum leaking out and I licked it off. As I continued to suck and lick his cock his hand moved down to mine and he began to stroke it. I could tell he was obviously very aroused and it would like not take much time before he came. The same was also true for me. The surrealist of the scene was very exciting. Soon I felt the head of his cock expand and I was ready for the first glob of cum.

"Oh God suck my cock! It feels so good," Tom moaned. His body tensed and his cock exploded.

I let the first expulsion of cum flow down my throat and holding my breath caught the second spurt. His dick kept spewing cum and I kept my throat open to it and managed to swallow all. By this time my cock was also erupting in my friend's hand. The way I was lying my cum shot all over his chest. As we both emptied our loads we collapsed. My head still rested between his legs as I let his limp dick slip from my lips. I would have never imagined this particular scene happening in a million years but here it was; it just happened.

We both lay there rather stunned.

"Wow, that was really something," Tom finally said as he began to wipe my cum off his chest. I watched him and at one point he took a glob of cum a licked it off his finger. He just smiled.

We did not talk much more that night. The next day we headed down the mountain and checked into a local motel. We were soon to be going home. Tom went to take a shower first and when he finished he walked back into the room totally nude. I noticed his cock was semi-hard but he said nothing. He just flopped down on his bed still naked.

"Okay, your turn for the shower," he said and laughed. As I walked into the bathroom I glanced back to see Tom lying naked on the bed watching TV.

I took a long hot shower and decided I would follow Tom's lead. I opened the door and walked back into the bedroom also totally nude. Tom had not moved from the bed. When he noticed that I was also nude he smiled.

"Have a drink," Tom said and handed me a stiff bourbon and water. I took a long hit.

We lay on our own bed having several drinks when I noticed Tom's hand move down and begin to play with his cock. It did not take it long to become hard.

"Did you like my cum the other night?" Tom asked.

"What do you mean?"

"You know what I mean. You swallowed all my cum and you seemed to like it a lot. So tell the truth," he replied.

"Yeah, I guess I did," I finally said. Tom watched me watching him and soon my cock was also hard.

"Does it turn you on to watch me play with myself?" Tom asked.

"I guess so, it is so strange to be here watching you," I answered.

"Why don't you come over here and suck on it," Tom said.

Almost mechanically I moved to his bed and grabbed his cock. I again took the purple head into my mouth and began to lick it.

"Damn that feels good," Tom said.

I sucked on his cock for a few minutes. I noticed he did not return the favor but he was now rubbing my cock. The alcohol had pretty much taken affect and I was feeling somewhat drunk but I kept sucking his cock. However, he suddenly pulled his cock out of my mouth.

"Let's try something," Tom said.

I looked up confused. I stood up and almost fell down.

"Damn, I think I had too much to drink," I said.

"Don't worry about it," Tom said. He pushed me back on the bed and I was now lying on my stomach. I could not see what Tom was doing. He said let me get something out of my bag. I did not know it then but he was putting some Vaseline on his cock. It was then I felt his dick slide up my butt cheeks and press against my anus.

"What are you doing Tom?" I cried. There was little I could do lying there with him on top of me.

"Owwwh!" I cried as his dick slipped inside me. It was painful but there was another feeling that began growing within me. I was lucky that Tom's dick was not very thick. There was some resistance at first but then his cock slipped deeper into my butt. As it slipped inside me the feeling of being impaled on his cock sent a shockwave through my body. It was unlike any feeling I had ever known. My own cock was pressed against my stomach and the sheet. It was harder than it had ever been. As Tom began to slowly pump his sock in and out of my ass the feelings intensified. I lost all sense of the strange act that two otherwise normal guys were doing. The fact Tom, my best friend, was fucking me in the ass passed from my mind as the feelings of desire deep inside my body took over my entire consciousness. All I wanted was for it to continue and at that moment I did not care about anything else.

"Oh God, your ass feels so good!" Tom cried. What began as something painful and embarrassing now had taken full control of me.

"Tom, it feels so damn good, fuck my ass," I said not believing I would ever say such words but not caring that I did.

Tom increased his pace and was fucking me hard. I could feel his cock pulling almost all the way out of my ass and then jamming back in so his balls slapped my ass cheeks. His cock head began to expand filling my bowels to capacity.

"Oh God, I cumming!" Tom cried.

As Tom's cock exploded inside me I felt his warm seed being spurted deep within my bowels. The feeling of his hot cum inside me was all it took and my cock exploded. It seemed as if I came forever. I never had such a ejaculation and as I lay on the bed with Tom collapsed on top of me I could feel the wetness beneath me where I had soiled the bed. It felt good.

We lay there for several minutes not quite believing what we had done. Tom's cock was still inside my ass as I felt it slowly shrinking and finally with a pop it came out. Tom rolled over beside me and we both passed out. I awoke the next morning lying next to Tom's naked body.

We arose and said little. Both of us had a hangover and we both felt very strange about the occurrences of the previous night.

The trip home would take another day. So, after a day of rather silent driving we pulled into a motel. We check in and decided to get something to eat.

"Would you do something for me?" Tom asked.

"It depends," I said curious as to what he wanted.

"I want to stop at some store and buy you some sexy panties. I would like to see you in them," Tom explained.

This trip was getting stranger by moment but there was something about the thought of Tom seeing me in panties that made me hot.

"I guess so," I stammered. We drove around for a few minutes and found a small woman's shop that sold a little bit of every kind of clothes including lingerie.

"Let's go in here," Tom said. We pulled in the parking lot and walk in the store. We glanced around and found the underwear section and proceeded there. I noticed there were only one sales lady and no customers. The sales lady looked to be in her early forties and was a little overweight. I was glad we were the only customers. I noticed the sales lady gave us a look as we walked over to the panties section.

"I think some silk panties are what we want. What do you think?" Tom said as held up a pair.

"I'm sure I don't know," I replied. Just then the sales lady walked us.

"Can I help you gentlemen with something?" she asked

"Yeah, we are looking for panties and a matching bra but we don't want to spend much," Tom said.

"And are these for your girlfriend?" she asked.

"Let's just say it is for a friend," Tom answered.

"What size does she wear?"

"I don't really know. Let's just say if I wanted some panties that would fit him," Tom said and pointed to my waste.

The sales lady looked at me and smiled. "Oh, I think these would fit him okay," she said as she picked up a pair of white silk panties and handed them to Tom. "Does he want a bra also?" she asked still looking at me.

"Sure, but he does not any boobs," Tom said and laughed.

"We have some padded bras you might like," the sales lady said and led us to the bra section. She picked one that matched the panties and handed it to Tom. To my embarrassment he placed on my chest.

"That looks good," he said.

"Do you need some hose and a garter belt to complete the picture?" the sales lady asked.

"Yeah, what the hell," Tom answered.

The sales lady went and returned with black stockings and a black garter bet. These should match the white well. Then the sales lady said something that made my legs feeling shaky.

She looked directly at me smiling and said, "Would you like to try them on?"

Tom smiled and said, "Of course he would. Is there somewhere private?"

"Come this way," the sales lady said. We went past the regular dressing rooms to what appeared to be a small break room.

"I think will do nicely and you won't be disturbed. Let me know when you are ready and I will come and check to make sure the size is correct," she said and left us alone.

"That woman wants to see me dressed in these," I said to Tom after she left.

"I think she does," he answered. "Now strip off those clothes."

I was soon standing naked before Tom. I slipped on the panties but my hard cock was not cooperating. I then put on the stockings and garter belt. Then Tom fastened the bra in the back. The padding in the bra made my chest look like I had some small titties. I felt really strange dressed like that with Tom looking at me but I also felt very excited. My cock was rock hard and pushed the panties straight out.

The sales lady then reappeared.

"Oh, it looks like everything fits quite well," she said as she looked over my body. I noticed her eyes spent sometime looking at where my hard cock pushed out the silken material of the panties. The sales lady had a slight flush in her face.

"I don't think that is going to do," she said looking at my panties.

"Let me try and adjust things," she said. She knelt down in front of my and took my cock in her hand. She moved it around inside the panties and I gasped. Her hand on my cock through the panties felt great. Finally, as she moved my cock around it slipped out and now she held it directly in her hand.

"I guess there is only one thing left to do," she said. "Go sit in that chair."

She pushed into a chair and then before I knew what was happening she was sucking my cock. Tom watched the action and decided he wanted to be part of the game. He walked over to the lady who might have been old enough to be his mother. He knelt down in back of her and reached and began cupping her breasts. When she did not protest he pulled her dress up. I had a great view for a long mirror across the room. Under her dress the sales lady wore black panties which Tom quickly removed. I could see her hairy snatch and Tom wasted no effects if finger fucking her.

"Mmmm," she moaned as three of Tom's finger went in the woman. She continued to suck my cock and rub my balls as Tom had his way with her pussy.

Tom quickly pulled his pants down to reveal his hard cock. He pressed it against her pussy a few times and then slid it inside.

"Ohhhh," she cried with my cock still in her mouth.

Tom began to fuck her doggy style and the lady was groaning.

"Ohhh," she moaned as an orgasm engulfed her.

I watched as Tom pulled his cock out of her pussy. He moved it up her butt crack and pushed against her anus.

"Oh God!" the lady cried in a muffled voice due to my cock being thrusts down her throat.

With a hard push Tom's cock already lubricated with the lady's pussy juice slipped deep into her ass.

"Ugggg," she moaned as Tom began to butt fuck her. It seemed Tom had a real thing for asses.

This was too much for me and my cock began erupting shooting cum down her throat. She gagged a few times but managed to take all the cum I had to offered. She held my now softened cock in her mouth as Tom pounded her ass. I could tell by his face he was near.

"I'm going cum in your ass," Tom cried and I could tell by his jerking body he was doing just that.

Tom slowly pulled his now deflating dick out of the sales lady's butt and we both sat back. The sales lady had a contented smile on her face and there were a few drops of cum on her cheeks.

"I think I will make a present of your new clothes. There will be no charge. Why don't you just wear them under your jeans when you leave? No one will ever know," she said.

Before I could reply Tom said, "Thanks a lot for the stuff and we do just that. Tom put on your jeans, we need to go."

Without much further thought I pulled my jeans up over my hose and garter belt. Then my shirt buttoned a little tight over my bra but not enough to make it look obvious I had breasts or at least fake ones.

"Bye," the sales lady said as she picked up her panties and put them back on.

We left the store, made a few stops, and then ate an early dinner. I had to be careful going to the men's bathroom. The first time I went there was one other guy in the bathroom. I went to the urinal as I would normally do not really thinking and when I zipped down my pants it took some effort to free my dick from the panties. In the process some of the frills of the panties and garter belt were plainly visible. I looked up to see the other guy giving me a very strange look. I was more careful from then on.

We soon returned to the motel where I still wore my girly outfit under my clothes. I knew the sex of the day was not over and there was another ass Tom wanted to invade. And surprisingly to me, the thought was very exciting.

It was turning dark as we entered the motel room.

"Take those jeans off and let me see your sexy underwear," Tom said as soon as he shut the door. It seemed he was ready.

"Let me use the bathroom first," I said. While in the bathroom I removed my outer clothes and walked back into the bedroom dressed as Tom's bitch. Tom was lying on the bed rubbing his already hard cock.

"Oh baby," he said looking me over. I was also getting into it and felt my cock begin to swell. I was attempting to hold it between my legs so the panties would not reveal it. I dance around a little and Tom was loving it. I walked over to his bed and crawled on. I pulled my self right between his legs and began to lick the tip of his cock as he continued to pump it.

Andy5v
Andy5v
380 Followers