Tailored

I was living on my own, six months on since my ex wife had walked out, and was still feeling my way in life, to some extent.

I had put off getting some new clothes for too long, but at least had saved a bit of cash, so I could get some better stuff. I hadn't decided exactly what to get yet, so I headed off to a clothing store in town.

When I got to the store I picked up a couple of shirts, but realised that I didn't know my size for trousers anymore. I had put on a bit of weight recently, and in any case, makers sometimes use different standards.

As I was pondering over which trousers to buy, one of the assistants approached me. He was in his 40s or 50s and sightly effeminate, with rather too much gold around his wrist, and a small gold chain around his neck. His hair was well cut, with some waves, and had clearly been coloured a sort of blonde.

My first thought was he was probably gay, although guys who work in these places quite often adopt an effeminate style.

"Hi, can I help you sir," he said. "I'm David. Is there something in particular that you're looking for?"

"Ah yes," I replied, "I need a few things, but I've realised I'm not sure of my sizes. Would you mind taking my measurements for me?"

"Of course not, sir," he said, taking a measuring tape from his pocket. "Lets get your chest, waist and hips first sir." He stood in front of me and slid his hands under my jacket and around my back, reading the tape at the front, then did the same for my waist and hips. He was wearing a nice aftershave and the closeness to him stirred something deep within me.

"Ok," he said, writing these down on a slip of paper, "lets get your inside leg then. Just stand straight up for me, please, sir."

As tailors do, he slid his hand, with one end of the tape, in between my legs, and, being careful not to touch my balls, he held it into my crotch and read off the length, down to my ankles.

Was I imagining it or did he touch my thigh just a tiny bit more than necessary?

He smiled as he gave me the measurements. "Once you find some stuff, give me a shout if you need any help at all sir."

I thanked him, but thought I probably wouldn't need any more help, so I started to browse the shelves and stands. After a while, I had a few shirts and a couple of very lightweight trousers. I moved towards the cubicle to try on the trousers, but ran into the assistant again.

"Hi sir. can I help you try these on?"

I would normally have waived away any help that I didn't need, but, and I don't know what made me do it, I accepted his offer. To tell the truth, although I'm straight, I had fantasised about gay sex for a long time, and there was something about this man, who made me feel at ease, even while he was touching me, and breathing on me, that I was finding exciting.

"Ok," I said, "that would be kind of you, uhm what did you say your name was?"

"It's David, sir" he smiled.

"Right, lead on David," I said. "I'm Jack."

"Ok Jack, we can use that cubicle there."

As we entered I could see that there wasn't much room for two! "Why don't we try your shirt for size first!" said David, opening one up.

"Ok," I said, starting to take my shirt off. He stood behind to help me with the sleeves. I could smell his aftershave again. Should I comment on it? Maybe, I thought. I had nothing to lose.

"That's a nice aftershave you're wearing, David," I said,

I could sense a slight pause in his response. "Thanks." he said, "It gets a bit hot in here at times so I like to wear some."

He came round to face me, standing back while looking at me and pressing his palms down my front, firmly. "Yes, thats a nice choice, Jack. Now if you slip your denims off we'll try these lightweight trousers on."

I couldn't help thinking David was looking more at me than the garments, but I was beginning to think he wasn't bad looking, for a guy about ten years older than me.

I took my belt off and let my denims fall to the floor. David bent down to pick them up. I could see he was looking at my crotch. He put them on a chair and held the trousers so I could step into them. By now he was really close, but not touching me.

As I zipped and buttoned the trousers, he went around me and. pressed the trousers onto me with his palms, For the first time I could feel my cock begin to get hard.

He stopped in front of me, "There is one thing I think you need for these, Jack," he said. "Because they're lightweight, they're smooth, and unfortunately you can see the outline of your jockeys through them. Why don't you let me nip out and bring you back some seamless briefs, which would be much nicer?"

"Ah Ok, "I said, a little cautiously. I was thinking, this means I have to take my jockeys off in front of him.

He came straight back with a pack of briefs I hadn't seen in the store. He took them out of the pack and I could see they were black and made out of some shiny nylon material. "Here," he said, "I'm sure you'll like these."

I took my jockeys off, and started to put these sexy black briefs on. Christ my cock was rising! I was having to push my cock and balls into the briefs, which, admittedly, were very sexy and quite a turn on. I saw David looking and tried to turn away. He caught my elbow. "Hey Jack,"he smiled, "these panties have a habit of doing that to my clients. Problem is, you'll see THAT even more through these trousers!" he laughed. "Do you want me to fix it for you?"

I wasn't too sure what he meant, but I felt I should accept. "Ok," I said. He put one arm around my waist and his other hand on my cock. I took a sharp intake of breath but I put my hand on his to encourage him. He kissed me. My god, I was kissing him in a mens cubicle, and I had a full erection.

"Wow, I thought you were a big boy and you are!", he said. He sank to his knees and pulled down the front of the briefs so that my cock sprang out. He took it into his mouth immediately and started wanking me.

I couldn't believe it, but I wanted it. I wanted to cum into this stranger's mouth. I wanted my whole cock down his throat. What was more, I could imagine his cock, and having it in me. I wanted to fuck him, and I

wanted him, with his golden chains and heady perfume, to fuck me.

I gasped, "Don't stop - suck me out, please!"

David kept wanking and suddenly I came into his mouth, and onto his face, over and over and over again. Luckily he had come with some tissues, and cleaned up quickly. "Jack you're so sweet," he said, "Would you like to come to my place later for a drink?"

I said I would and he gave me a note of his address. "Say 6.30pm" he said softly.

I had time to go home first, grab a bite to eat, then shower and shave before heading out to meet David. Part of me said this was stupid and dangerous, but another part of me longed for mysterious sex.

When I rang David's bell he answered quickly. He was wearing a loose fitting linen shirt, open to his chest, which was shaved, and loose linen trousers. "Oh hi Jack," he said, "thanks for coming." He kissed me lightly and showed me through to the lounge.

On the sofa there was another guy, younger, with a nice tan, and well dressed. David spoke again, "Jack, sorry I should have mentioned that Mike would be here. Mike's my partner. Mike, this is Jack that I was telling you about."

Mike stood up and we shook hands. He was wearing a very musty eau de cologne, and I could see a hint of eye liner.

David brought out some prosecco and we sat on the sofa, with myself in between David and Mike. After some small talk David leaned towards me. "Do you like watching porn, Jack - I can put some on if you like!"

My mind was racing. I felt good on the sofa, enjoying the prosecco, and I had expected some sort of sex, but Mike's presence had unsettled me a bit. On the other hand I could hardly say no, given our earlier encounter.

"Yeah, that would be fun," I said, feeling my cock beginning to grow in anticipation.

Jack put some gay massage on, where a straight guy was beginning to enjoy being touched. As we watched, I could feel David begin to stroke my thigh. I glimpsed along at Mike.

"Oh don't worry about Mike, he likes to watch, and also to join in, if you like," said David.

I was now almost erect and wanted David. I put my hand on his cock and he opened his fly for me. I took his cock out and started wanking him. He put his hand behind my head and pushed a little, I let him push me all the way down. I wanted him to put me onto his cock, and he did. Oh God, I had never been with a man but it was so exciting! His meat was so hard but hot and wet. I sucked it and hoped he would cum.

As I was sucking I could see Mike out of the side of my eye. He had his trousers off and was wanking. I reached over with my hand and he put it round his cock. God I thought David's was big but Mike was huge!

I started wanking him, feeling him getting even bigger. As his girth increased I squeezed him harder. I was in bliss when David pulled me up and kissed me. "Mmmh Jack," he said, "you were wonderful this afternoon but this is amazing. Would you like to have full sex with us? We'd love to do it with you."

I nodded, "mmh yes, but I've never done it"

"That's Ok we'll go very gently with you and only speed up when you say so. Its best for me to start with you though, since Mike is big big boy!"

By now we were all naked. I turned to Mike and started to suck him. He bent over me. Kissing my neck he murmured "Don't worry Jack, you'll be able to take me later once you get more relaxed. Keep sucking though - its so good!"

As I kept on sucking Mike I felt David touch my arse, and then he was on his knees licking around my hole. I moaned loudly, and gasped "Yes David, yes." He pushed his tongue into me, working around me, til I thought I couldn't get any harder. Then David pushed some gel into me and started pushing a small butt plug in me which I took quite easily. I had drunk quite a lot of alcohol by then, so I guess I was fairly relaxed.

Now David put his cock into my anus and began to move ever so carefully. I was moaning for more but he held back, sliding his hand down to my balls, and pulling my cock.

As David was pushing his cock further and further into me I was bringing Mike to a climax. His cock was hot and throbbing and it was all I could do to get any of it in my mouth. But I could hear him screaming and his cock was suddenly convulsing into my mouth. His cum was so much, it quickly filled my mouth, and continued to spurt onto my face. I loved the hot sensation, swallowing some and rubbing the rest around his cock, and behind him into his beautiful crack.

I was now in real ecstasy. David was an anal expert, and I didn't want it to end. I did want to please him, however, since I would have experienced nothing without him. I turned to him over my shoulder and whispered, "David please cum into me now. I want to feel it."

David briefly upped his thrusts. I felt him more accutely, and I felt his jets of semen hitting the walls of my rectum. I was in bliss. "Thank you David," I said. We lay on the floor and he kissed me passionately, while we continued to tease each other in every part of our bodies.

All of us sat up again on the sofa, and David topped up our glasses. I excused myself to go to the loo. Mike directed me through their bedroom.

When I was crossing the bedroom I couldn't help noticing a 'walk in' wardrobe that seemed to be filled with women's clothing, hangers full of dresses, underskirts, camisoles, and drawers of such dirty panties.

When I got back to the lounge I asked the guys if it was only them that shared the house. "Ah," said Mike, laughing, "I see you found our play cupboards! These are just for our playtime. Do you like to dress up, Jack? Because if you do, we could have a lot of fun."

I had always liked to put on my ex wife's panties, and this sounded like a lot more sexy fun to me. "Yeah I said, "I'd like that a lot"

"Jack," David said, "this has been really great tonight, but I think it will be better for you if we break off now, and get together in a couple of days. Then we'll take you through our wardrobe and I think we can raise the bar a few levels. We do have a few more friends who get into role playing with us, so if you like, we could invite them and we'll go out for dinner and a dance.

I thought to myself, it sounded exciting, so I agreed, "Sure, David, I know I'm in good hands with you and Mike!"