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Trying Something New

Category: Gay Male
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I was always an avid reader. Now I had broken up with my girlfriend, I had more time to read.

I shared a flat with my mate James. He worked for a local software house, whereas I was a student. I was home most of the day and he came home late. Both of us were in the same position however, his girlfriend had left him to go to America not one month ago.

About a week ago, James came into my room. “Mate, I’m bored shitless. Have you got a book I can read?”

“Yeah sure,” I said, and reached over for one from the shelf. I chose one at random, not really thinking about what it was about, or its implications.

“Cheers.” He said, and left.

Now a week later, James was back in my room.

“Strange book that mate.” He said.

I took it off him. “What was it? Oh, I haven’t read it yet. Most of these books are ones I picked up at a jumble. What was it about?”

“About a guy finding his sexual orientation.”

“Ah.” I said. How embarrassing. “Okay. Sorry about that.”

He shrugged. “Never mind.” He said, and wandered back into his room.

I thought over what he said. I had never ever had sex with a guy. I thought about it once or twice, but never wanted to try it. I picked up the book I had lent him, and skipped through it. I stopped at one part where the main character asked to try gay sex with his best friend; his excuse was that no one would find out, because they would keep it to themselves, and at least they knew that they were both clean, and nothing to worry about.

I put the book down, and walked into James’ room.

“Erm, ah, you know that book?” I asked.

He looked as if he knew what I wanted. “Yes?”

“Have you ever thought about doing something like that? I mean, trying it…once, with your mate? You know, it wouldn’t be gay would it, we’d only be trying, and we both know we still love girls, it would just be trying, wouldn’t it?” I said, nervously.

“Huh, yeah, I suppose I thought about it when I read that book. I thought you gave it to me for that reason. Haha.”

“Ha, yeah, well, I didn’t. Erm…do you want to try it?” I asked.

“Yeah, okay. But let’s just sit and watch some porn or something and then see how we go on.”

“Okay, should I go and get a cassette? From the local?”

“Yeah, go for it.”

So I quickly ran down to the local porn shop to rent a video. I found a gay one that looked fairly decent and one bi one and handed them to the girl on the counter.

“Are you a member?” She asked.

“No, how do I join?”

She handed me a form. “I need something to prove you are eighteen, and you must fill out this form.”

I handed her my driving licence, which she approved, and filled out the form.

“Oh, Gay Lovers in Action, and Bi-sexual Lingerie Fantasies. You bi-sexual then?” She asked. Why was this twenty-year-old girl questioning me?

“Errr…no, not exactly.” I replied.

She smiled and stroked my cheek. “You don’t need to be ashamed you know. I’m bi-sexual too. I’d love to meet a guy who would fuck me while he was being fucked up the ass.”

Now she was turning me on. “Maybe I could come round and join you one day?” She continued. “And look, bi-sexual Lingerie Fantasies. So you like transvestites, or you are a secret tranny?”

“No, I’m not.” And to be honest, I never even thought of it.

“Well, if I can come round one day, I’ll bring some really sexy underwear for you and your boyfriend to try on. Maybe you’ll like it, and you’ll become a tranny. What do you think?”

“Erm, well I don’t know. I’ll let you know.” I was really interested in getting this girl back to the flat one day, but only because she was drop dead gorgeous! Tall, thin, long black hair, which she kept pushing behind her left ear, and an innocent smile.

“Well, enjoy the films. Don’t shag too much.” She said.

I said thanks and left.

When I got home, I told James what happened. He laughed it off, saying it was definitely only a one-time thing and that I would have to find another boy to share with the girl.

James put in the film called Bi-sexual Lingerie Fantasies. It was only 5 minutes in and I was rock hard. I wasn’t sure if it was thanks to the film or the fact that I would be making love to the guy sitting next to me. Either way, none of us had the nerve to make the first move.

As we watched one transvestite dressed in sexy green lingerie fuck another transvestite in a red corset up the arse while another licked out a woman, I decided to go for broke. I unzipped James’ trousers and pulled them off. James got all-tense. I lifted off his t-shirt, leaving him in only his boxers.

I got undressed completely. Then I pulled out James’ rigid penis and started to play with it. He was really nervous.

“I think we’d both better just relax.” I reassured him. “Think about it James. We are both clean, we are both really turned on by this, and nobody can find out! Can they?”

I relaxed a bit. “No they can’t.”

“So, we can try this just the once. At least we can say to ourselves we’ve done it, and we know what it’s like!”

“Okay.” James reached over and started to pump my nine-inch penis. James had a similar size to me, just a bit thinner.

We watched the film a bit, tugging at each other’s dicks. Then James leaned over and kissed my lips. It was just like a female kiss, but the whole feeling of kissing another boy made we shiver with excitement. I worked my way down his neck, kissing and sucking. When I reached the join of his neck to his shoulder I sucked harder, at the same time I pumped his penis harder. He suddenly shuddered, wrapping his arms around my back pulling my face harder into his neck. He came hard, pumping cum all over my hand and body.

We kissed again while I pumped the last of his cum out of his dick, then he suddenly pulled away.

“I can’t do this.” He said, pulling as far away as possible.

“Mate, have you ever dreamt about something while wanking, and then after you came, you thought, ‘god, why did I think about that??’?” I asked.

“Yeah, I did.” He replied.

“Well that’s this! It’s just a feeling, it’s just hormones. If you come back to me here, and let me continue to rub you, you’ll feel good again. You just have to beat the hormones!” He thought about it, then came back over to me.

I started to rub his cum all over his body. Nipping at his neck. On the TV, we watched two transvestites in really sexy satin chemises; fuck a woman in her pussy and mouth, while another transvestite took the man fucking the woman’s pussy up the arse.

James started to respond. His dick was already hard again, and now he was rubbing me all over. I moved my mouth down to his nipples and sucked on them.

“Sorry about that Paul.” He said.

I looked up at him. “No problem sweetheart.” I smiled, as if it was a joke. He smiled back.

“Those transvestites are actually pretty sexy.” He said.

“Well, you still have your ex-girlfriend’s clothes here. Maybe after this, if we want to experiment a bit more, we can try them on?” I replied.

He smiled. “Yeah, that’d be cool.”

I kissed him on the lips, and our tongues mingled for a few minutes. Then I moved down his body, and put his penis, which was still covered in his cum, into my mouth. The cum tasted slightly salty, but not as bad as most girls made out. I bobbed up and down on his cock, running my tongue along.

James dropped his head back. “My god, this is the best blowjob ever!!”

I continued sucking until he start shuddering again. He grabbed my head and forced it further onto his dick. “Uuuuaarrrggghhhh!!!!!!!!!!” He screamed as jets of cum hit the back of my throat. I sucked out more and more and tried to swallow as much as possible. Eventually I sat back and smiled at James, cum dripping from the side of my mouth. I pushed it back into my mouth and swallowed.

“What was it like?” James asked.

“It actually tasted quite nice!” I replied. “And I enjoyed sucking your cock. I think I’ll continue doing this in the future. Only with you though, if you don’t mind.”

He smiled, “no, that was nice. You can blow me any time you like. I’ve got that feeling again, but not as bad as last time.”

I kissed him on the lips and held him tight. “Don’t worry, it’ll go away.”

And it did. The film had finished, so James went to put the other one in. We started to watch it. It was a group of young guys swimming suddenly have a gang-bang.

My hard-on still hadn’t gone down, and now James was hard for a third time. James said it was his turn to blow me. He went down on my dick and sucked and licked, trying to imitate my moves. It felt brilliant as I ran a hand through his hair. At the same time, I took in what was going on in the film. The studly cleanly shaven boys were all having anal sex.

“Oh my god. Ah baby I’m gonna come! Yes James baby suck me!” Then in an instant I filled his mouth with my come. I suddenly felt that feeling James had, that this was wrong, but I overcame it by grabbing James and kissing him, hard. I tasted my come in his mouth, even though he had swallowed most of it.

“You called me baby.” He said, smiling as he held me tight, resting his head on my shoulder.

“Yeah, I was taken in my the moment.” I apologised.

James laughed. “I don’t mind,” he ran a hand through my hair, then pulled me towards him. “That was quite nice. I enjoyed that. Okay, so I think we can give each other blowjobs from now on, okay?”

“Yeah, sure.” I said, smiling.

“And you, sweetheart;” James ran a finger down the crack of my ass, and started rubbing my hole. He worked it slightly in and out. “Can call me baby anytime when we’re doing it.”

I beamed. “Okay baby.”

He pushed his middle finger all the way up me as we kissed. We turned to watch the screen. It focused in on one of the guy’s dicks going in and out of the man’s arse.

“That guy is very beautiful.” James said. “You ready to do it?” He got up and pulled out a tube of KY Jelly from a drawer. As he walked back over to me, I looked at his long penis sticking out at full mast. “Get on all fours and face the telly.”

I got into the position he said; my penis was hard again. He got back on the bed and positioned himself behind me. Then he squeezed a large amount of KY onto his fingers, and worked it up my bottom, then on his penis. As I watched six guys fucking on the telly, I felt the tip of James’ penis press against my hole. I tried to relax as much as possible, but as the head of his penis went inside me, I cried out in pain. James asked if he should stop, but I told him to go on.

He pressed another two inches in, and asked if I was okay.

“Yeah, it hurts, but now in a weird way. It’s quite nice. Keep going.” I said.

I felt filled up as he pressed what felt like another five inches in. Then I felt his body touching my buttocks.

“I’m all the way in.” he announced.

“Then fuck me babe, fuck me!” I shouted.

He pumped in and out of me, god I was in heaven! It felt so good, I didn’t want it to end. My penis was buzzing. I tried to turn my head to see James’ expression. He was smiling.

“How’s it feel Paul?”

“OH! UNBELIEVABLE!!!” I screamed!

“Ah honey, for me too!!!”

He bucked and rode me hard. Then he pulled out and turned me over. I put my legs on his shoulders and he pushed back into me. Once he was fully inside, he leaned over and we kissed. Then he kept on pumping, faster and faster.

“Oh baby. Yeah Paul, baby. OH I LOVE YOU!!!” He came inside me. I could feel his warmth splattering my insides! He collapsed on top of me. I stroked his hair and back as I could feel his penis shrink. “How was it Paul?” He kissed my neck and ears.

“It was great!” I replied.

“Sorry about the love you thing, heat of the moment, you know?”

“Hey, don’t worry about it babe. We’re lying here together, you’ve just taken my virgin ass, so I don’t think it matters.”

“Cool. My turn!” Said James.

I turned him over to face the telly and KYed his hole, rubbed some on my dick, and started to press against his hole. On the TV, two guys were making love side by side on a bed, it was such a turn on. I pressed harder against James’ hole and went in. James shrieked in pain, but I ignored it, I knew what would come next. I continued to push, inch after inch, till I was completely in. Then I started to pump in and out of him.

“Oh, god, that’s so good.” He said.

I continued to fuck him, at the same time, I wanked his penis. I couldn’t believe it, he came all over my hand really quickly. Where was he storing all this cum???

I licked most of the cum off my fingers, and fed some to James. Then I felt my orgasm come. I felt like I had burst something, because a massive amount of come filled James’ insides, all the time I could feel his own cum run out of my arse.

“Baby, that felt amazing!!!” James said, as he pulled off my penis and jumped on top of me. He hugged me and kissed me all over. “Let’s keep doing it, just you and I. You can move in to this room and we can sleep together. Nobody needs to know.”

I held him tight and kissed his forehead. “Sure James. I’d love to be your boyfriend.”

We kissed and made love all night, this time with no hesitation or nervousness.

We woke up in each other’s arms the next morning. It was a Saturday, so no work, and more time for loving! We spent the first hour of the morning having oral sex, and generally cuddling. Then we had a bath together.

While I was eating breakfast, James got a large box down from the cupboard.

“This is all Susan’s stuff. I spoke to her recently, saying I was going to throw it away. She said do it, so officially it’s our to do with as we please. She took as much as she could with her to the States.”

We opened the box. There were some towels, some old books and underneath all that were all her clothes.

I pulled out a pair of red leather trousers, and a rubber tank top. James found the matching rubber skirt. There were plenty of sexy clothes for us to try on; different types of blouse, skirts, tops. Then we found the pot of gold, her underwear bag. She’d obviously taken only her normal underwear, because all her sexy underwear was still there.

James held up a scarlet lacy teddy with suspender straps. “God, I never knew she owned this stuff.”

I found myself a dark green basque, with matching sheer stockings. I put them on.

“Hmm…sexy, but I think we should shave our body hair first.” James said.

So we did. Then we put on our newfound clothes. First we admired ourselves in the lingerie, then we put on a sexy blouse and skirt. We looked amazing. We felt amazing.

“This feels so nice.” James said.

I walked over to him, and we kissed, feeling each other in our new clothes.

“I have to go and return those videos.” I said.

“Like that???” He asked.

“No silly. But I will wear the underwear I’m wearing now.”

“Won’t it be visible under your t-shirt?”

“I’ll wear a coat. What about that girl?”

“Try and get her to come round.”

I got changed, keeping on the basque and suspenders, and went back to the adult video store. Sure enough, the girl was still there.

“Ah, my friend. How did you like the videos?” She asked.

I smiled. If she can flirt with me, I can back, anyway, the shop was empty.

“They gave us a few ideas. For instance.” I lifted my t-shirt up to show her the sexy green lacy basque.

“Oh my god, I think I just came looking at you!” She said. “I have to have you! I have to have you dressed as a woman. Can I come round, please???”

I went behind the counter, lifted her black vinyl skirt, and plunged my fingers into her pussy. I rubbed her really hard a few times, then I got under the desk, pulled her knickers down, and licked her pussy. I continued, even when a customer came in.

“OH!” She let out.

“Excuse me?” Said the man.

“Nothing. There’s this really sexy man dressed in sexy women’s lingerie underneath this table licking out my pussy.” She replied.

The man looked surprised. I nearly burst out laughing.

“Oh, okay.” He continued looking for a video, but changed his mind and left.

I stood up, opened my fly, pulled my knickers aside and whipped out my dick. The girl backed up against the desk, and lifted her mini-skirt. In one swift movement, I was in her pussy, fucking her.

She lifted up my t-shirt, feeling the material of the lingerie on my body. Another customer came in, a woman. She saw us fucking and was about to go out when she changed her mind, came over near us, put her hand in her knickers and frigged herself.

All of a sudden the girl I was fucking orgasmed, and I came inside her.

“Quick, let me at her.” She said as she jumped off me and dived between the woman’s legs. She licked at that pussy like mad, then they lay on the floor and she put her pussy full of my cum over the woman’s mouth. They licked at each other like crazy until both shuddered to a massive orgasm.

“Wow, I only came in for a video. This is amazing. That’s what you call customer service.”

We laughed. The woman left the shop, thanking us for an amazing show.

“I’m Christy.” Said the girl.

“Paul, hi.” We kissed. “Christy, you are welcome anytime you like at our place. When can you come?”

“Well, my shift ends in an hour, can you wait here with me?”

“Sure. I can use that time to explain about what happened last night.”

So I went into detail about what happened. When I finished, Debbie, the girl who was supposed to relieve Christy had already arrived, made herself a coffee, and had listened to half of my story. I had to repeat the other half for her.

“So let me get this straight.” Said Christy. “When I flirted with you last night, and you rented those videos, you were still straight?”

“Yes.” I replied.

Debbie cut on. “Let me get this straight. Christy, so you’re going round to there place now, to have sex with two bi-sexual transvestites, who only discovered they were bi-sexual yesterday?”

“Yes.” She said.

Debbie smiled. “You lucky bitch! Give me your address Paul.” I gave it to her. “I’m coming round tonight after work. I’ve been dying to eat Christy’s pussy for ages anyway!”

Christy studied her. “Have you? Oh. Well, why didn’t you?”

“Didn’t know you were that way inclined.”

“Cool, then it’s settled.” I said. “Come round tonight, and we can have one big orgy.”

“Woohoo!” Debbie cried.

Christy and I stopped off at her flat to pick up some things. Then we stopped in a wig shop and bought one long curly brown haired wig, and one long straight blond for me.

When we arrived home, James was still dressed in the skirt and blouse. We made the introductions, and I got changed. Christy put the wig on James and made up his make-up. James looked really amazing now. Then Christy did mine.

Christy told us to wait on the bed. “I’m going to get ready. Today is going to be my first gay day.”

When Christy returned, she was totally naked, save for the large strap-on penis she had on.

“Okay, I want to feel like you guys, so no sex in my pussy today, okay?”


Christy slowly began to undress us, leaving on only our lingerie. She pulled down my panties, and unclipped James’ teddy.

“Now, give each other a blow job.” She said.

I climbed on top of James, placed my penis at his lips, and began sucking at his. Christy began rubbing KY jelly on my hole, and pushed her dildo into me. It was unbelievable. I was being fucked up the ass by a girl, while blowing and being blown by the most beautiful boy in the world.

All of a sudden I came in James’ mouth. Christy immediately jumped down to kiss him. I saw them passing the fluids between their mouths. James then positioned himself behind me and rammed his penis inside my arse. It didn’t hurt because I was already well lubricated. Behind James, Christy was taking his arse.

We were all banging away when the doorbell went.

Christy went to answer. We continued to fuck.

“Hi Debbie!”

“Hi Christy, I see you have your strap-on. Have you got one for me?”

“Yeah, babe, of course. I thought you had to work.”

“I phone the boss, told him business was slow and I felt ill. He told me to lock up early and go home. I was to excited to wait, so I came straight over.” Debbie immediately began to strip.

“Guys, Debbie managed to get off work early.” Christy announced.

“Great, come and join in the fun!” I shouted.

Debbie, now naked, was staring at the two trannies making love to each other.

“That is so sexy!”

“Hey Debs,” said Christy. “No sex in the vagina today. We’ll do that tomorrow. Today, is gay day. We are going to do everything up the arse.”

“Sure, okay.” Agreed Debbie, as she pushed the pussy dildo up her vagina, and strapped on the rest of the strap-on dildo.

“Debbie, you take James up the arse, and I’ll receive from Paul.”

We all gang banged like that all day, in different positions. At around eight at night, we decided to give it a rest, as our arse holes were getting sore. We cooked some dinner and watched a film on TV.

After the film, the girls decided to play dress-up. They dressed us up in lots of types of clothes.

“Paul, what do you prefer? Sex with a boy or a girl?” Christy asked.

I thought about it. “I like both just as much. But I prefer both at once.” Everyone agreed that was truly the best. “James, yesterday night you told me you love me, but then quickly said it was a mistake. Well for me it isn’t a mistake. I truly love you, as my boyfriend. I’m glad I’ve found out what gay sex is like, I’m glad it is with you, and I’m glad you are my gay lover. And Christy, I’m glad I met you. I hope you will move in with us and be my girlfriend?”

Christy kissed me. “I will.”

“The same goes to you Debs, I hope you’ll be my girlfriend and move in with us. We’re going to need a bigger bed if four of us are to fit in here.” James said.

“Yep,” said Debbie, “we will won’t we!”

A big smile formed on James’ face as he kissed Debbie. Then he turned to hug me. We kissed passionately. Debbie climbed over and began kissing Christy, adjusting their strap-on dildos so they didn’t get in the way.

“I love you too Paul.” Said James. “When I read that book, I wanted to try sex with you more than anything. I never ever thought of you this way though. Now I look at you, and I see how beautiful you are. I’m so lucky to have you, my lovely baby. You have such a beautiful penis.” We kissed again.

One year later

We live all together now. We actually got married. Yep. Christy and I got married the same time as Debbie and James. None of my mates know that I secretly married James too.

I have a bigger wardrobe of female clothes than male, as does James. Went we are dressed as women, James is called Jane, and I’m Paula. We often visit gay clubs, where we like to dance dressed how we feel comfortable.

One thing we find really sexy now, is when Debbie fucks my arse, and James faces me and I watch Christy fuck his arse. It’s also good because we like to kiss a lot.

James and I have recently gathered enough courage to kiss in public. We all hold hands in public, and our friends are starting to know that we are bi-sexual. One or two of my friends try to avoid us now, but most are cool with it. All the female friends find it cool and really sexy.

Tomorrow night, we are planning an orgy. Some of our friends are coming round. Most of our male friends, and all of our female friends are up for it. But that’s another story.

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