Night Out with the Boys

David had chosen saturday for the dinner and dance since it would take Jack, Mike and himself several hours to get ready in the afternoon.

Jack was a little apprehensive about being a woman in public but David greeted him at the door with a long passionate embrace and made him feel at ease.

"Its great to see you again Jack." said David. "I know you're going to love it. Joe, Louis and Steve are really nice, and incredibly sexy!" David showed Jack a picture of them, naked, and all with erections.

"God!" exclaimed Jack, "they're gorgeous!"

"Yes, aren't they just." replied David. They are all bi, and Louis and Steve also have wives. The wives are bi too, and they don't mind them being with us at all."

David took Jack through to the dressing room, where Mike was already putting on his makeup. "Its probably best if you let me shave you and put on your makeup, Jack." said David. "We try not to look like tarts so we keep the makeup understated,and wear clothes that aren't loud, if you get me. Its best if we shave your forearms as well, Jack, and I've got a nice bracelet you can wear."

Jack was getting turned on. He had a shower and let David shave him completely. "Here, Jack," said David, handing him a pretty pink gaff. "That'll keep your cock from showing too much. Its useful if one of the guys makes you hard on the dancefloor. I've also got some little relaxing pills that'll ease the sex for you, if you decide to let one of these guys inside you!"

"Wow," said Jack, "you really think of everything!"

Next thing was for Jack to be made up, and Mike did this since he had finished his. Mike was now a brunette with pastel pink lipstick, light brown eye shadow and matching face powder. As he started on Jack, he put his hand on his cock. "Jack," he said, "you're going to make a lovely lady. If I wasn't a lady tonight I'd like to have you for myself."

"Another time then Mike, that would be nice." said Jack, squeezing Mike's hand on his cock.

Mike made Jack up as a blond with neck length hair, green eye shadow and neutral colour on the cheeks. He then took Jack over to the clothes.

Jack chose black stockings with suspender, a black lace underskirt and a black bra specially made for a man. He also took a pair of pink silk panties, to wear over the gaff, and finally a black shift dress with sparkles.

Mike lent him some thin gold chains and some gold drop earings to complete the look, apart from shoes, which David had bought for him. High heels were out of the question for a beginner, so David had picked up some almost flat black sandals, with a bit of gold fleck.

When Jack looked at himself in the mirror he could hardly believe it. He thought to himself, mmh, very fuckable, and with a touch of class.

By now it was almost time for the guys to arrive. David offered one or two last words of advice. "Just a couple of things Jack, for the role play. Try to speak softly but not with any attempt to sound female. When you're dancing remember you hold his right hand with your left and if he wants to put both arms around you, put your hands on his collar bone. You can so easily make contact with his cock from that position. If he does get a massive hard on it would be polite to stay on the dancefloor long enough for it to subside!"

The guys love the role play, and will treat you like the beautiful lady you are. You're very lucky, Jack, that you have thin wrists and ankles. You could fool anybody!"

One last thing that David gave him was a gold ankle bracelet, the absolute best accessory to drive a man wild. Its like a signpost to a woman's pussy.

Jack felt so sexy. He began to move around the room with small steps, imagining himself as a woman ready to be courted and taken by some handsome guy. "Wow, Jack," said David, "I feel like cancelling this and just taking you to bed. Maybe tomorrow?"

"I'd love that David," said Jack.

The boys arrived together, looking incredibly suave, in sharp suits. As they all knew each other there was a lot of kissing and laughter. David introduced Jack to Louis, Joe and Steve. From the start they treated Jack in all ways as a woman. They kissed her cheek, shook her hand gently, and there was no swearing.

After a little while it was becoming clear to Jack (whose name for the evening was Alice) that both Steve and Louis had gravitated to Mike and David, leaving Joe, he thought, for him.

Joe was a beautiful man. He was clearly part spanish, with very dark eyes and a toned body. Jack could just make out some dark hair under his shirt cuff and, when his shirt parted ever so slightly at the buttons, a mass of dark curly hair on his chest. "So Alice," he said, "how did you come to know these ladies?"

To keep in role, Jack had to resort to some little white lies. "Well it was just a chance meeting," he said. "I was in a lingerie shop a little while ago and Anne (David) was so kind, helping me to choose. We discovered we had quite a lot in common so Anne invited me for a coffee and I met Lynn (Mike). I love them both and it is so nice that they've invited me to join you tonight."

"Well I'm so pleased they did, Alice. You look really amazing!"

My god, thought Jack, I think I'm actually blushing! I can't believe it. I actually feel like what I imagine a woman might feel (apart from my hard cock)!

After quite a few drinks they ordered a couple of taxis and went to the hotel. When they went into the reception the guys all checked in. Jack had not known about this, but David explained that it got rid of any problem in using the ladies toilet, and also gave them privacy should anybody want it!

When they moved into the dance hall they had a circular table, and sat around it, boy,girl, boy, girl etc. Jack was between Joe and Louis. Like Joe, Louis also complimented Alice on her looks. Jack felt really happy. He had hoped he wouldn't look like a man in drag and this reassured him.

After the dinner the music started and the lights were dimmed. Strangely, it seemed to Jack, it was Steve, and not Joe, who asked Alice up to dance. Jack let him take his hand and lead him to the floor. As he took Steve's hand and put his other hand around him Jack felt again what, he thought, it must be like to be a woman.

Steve was taller than Jack, with longish blond hair and broad shoulders. Jack could feel his hand rubbing his back through the dress and underskirt. He was wearing expensive scent and Jack relaxed into his arms. Steve was a good dancer and his whispered conversation was nice, staying perfectly in role, treating Jack as Alice.

It was not long before Jack felt Steve's cock against his dress, but Steve was not pushing it. Jack wondered whether he should wait for Joe, but he saw him cosying up to Mike, so he decided to respond to Steve.

Imperceptibly Jack put some pressure on Steve's back and moved a little closer into his arms. Steve squeezed Jack's hand gently and pressed his cock into her dress. Jack leaned into him and whispered "Steve, I'd like to get to know you a lot more"

Steve replied, "Me too Alice, you're really sweet, and I love that perfume you're wearing."

"Mmmh yeah, I put it on all over. Maybe I'll let you get closer to it later - if you're a good boy."

Steve's cock was now pushing up against his fly. He changed hold and wrapped his arms around Jack, who then brought his hands up and around Steve's neck and kissed him.

"Alice I want you, can we go upstairs?"

"Of course, darling," said Jack, "I want you too, but you should let me walk in front of you to the lift - unless of course you want to show off your massive cock to everyone!" Jack smiled seductively.

When the lift door closed on them Steve pulled Jack to him and kissed him deeply. His hands were grasping Jack's arse, and then he pulled his dress up and plunged his hand between Jack's legs. "Jesus Alice, I knew you were a man but I just can't believe it. You really are so beautiful! - and so wet, honey."

He kissed Jack again and when the lift came to their floor they ran to the room, When Steve opened the door they ran to the bed and Steve immediately pulled Jack's pink gaff and panties off, allowing his cock and balls to fall free. Steve took Jack's balls into his hands and opened his mouth to receive Jack's throbbing cock.

Jack's cock was rock hard. Steve was now naked with a huge erection pointing skyward. Jack took the dress off, but left the slinky underskirt and black stockings on. He kneeled on the bed and Steve, expertly parted his hot buttocks and penetrated him.

Jack had never felt so good. Steve had treated him exactly like a woman, with enough force, so that Jack felt gloriously submissive. He was now being stiffly fucked by a real man who knew how to handle him, to turn him over and suck him, then to fuck him even harder.

Jack shouted in ecstasy "Fuck me again Steve, I love your cock. Push it all the way up."

Steve did, and kept it there, feeling the glorious mixed feeling of fucking a woman whose body was harder and more muscular, but who had such sexiness and beautiful clothing, and looks.

After a quiet time, where each simply felt each other deep within, Steve began to thrust again, slowly at first, but then getting faster and harder, much harder now, pushing and twisting til he brought Jack to a final bursting moment of true bliss.

Steve held Jack close and whispered to him, "I love you Alice. You are the most beautiful woman I know."

"I love you too darling Steve." echoed Jack. " I just want to be with you, with your hard cock inside me, and your tongue all over me."

It took them a while to come down from their ecstasy, but then, after a while, Steve pulled Jack nearer and spoke softly "Alice, you know I'm married. My wife, Dawn, asked me if she could join us. Would you fuck her for me?"

Steve skyped Dawn and showed her to Jack. She was lying on the bed with her legs spread wide and her finger just inside her pussy. Jack's cock was rock hard again. Steve put his hand on him, "I'll take that as a yes then!" he said.

Jack went to the loo to freshen up then came back to the bed. "Do you think I should put the dress back on Steve?" he asked.

"No," said Steve, "I sent her your pic and she's crazy about you already!"

"Ok then, I'll just slip on an extra pair of pink silk panties I brought in my handbag!" he smiled at Steve.

"Wow you're amazing. We've got time for another quick fuck before she gets here!" Steve hoped.

"No, you're a naughty boy, and in any case I don't do 'quick fucks' I like to make love and it takes time honey." sighed Jack.

"You're right of course," Steve was saying, as there was a knock on the door. He went to the door and opened it slowly. Dawn stood there in a light coat, wrapped tight around her.

Jack stood up to greet her "And you must be Alice," she said. Opening her coat she revealed nothing but a black 'see through' body stocking, with wide open crotch, rear hole and nipple holes. She already had a rock hard, and shaved, mound, which bulged out of the black nylon and shone, as she pushed her hips towards Jack.

"Wow you're beautiful!" said Jack

""And so are you Alice" Dawn smiled, and kissed Jack, pulling him towards her.

"Alice," said Steve, "don't worry about me. Just go ahead and fuck Dawn. I'll just make a little video, if that's Ok with you?"

"Mmmh yes that would be nice" said Jack, and let Dawn pull him gently on to the bed. He thrust his hand down, immediately grasping her gorgeous mound, then into her, and kissed her deeply as she gasped in shock, with Jack's fingers exploring deep within her.

Jack was in heaven with this beautiful lady. His hands were moving rapidly up her legs and into her crack. He thought that since she was with Steve, she probably did anal. Softly he pushed a finger into her anus.

"Oh yes Alice that's good," said Dawn," if you want it. But let me suck you first." She pushed Jack down and pulled the panties off. When Dawn took his cock into her mouth he had never felt his cock going so far down anyone's throat before. It was amazing. He would have cum right then but he didn't want to disappoint her, so managed to slow himself down.

He came back out, and turned her over, smacking her buttocks playfully. "Naughty boy!" she shouted. Steve was wanking himself from the bedside while filming, "Nice, Alice," he said "now fuck her arse raw, fuck her hard for me!"

Jack now mounted Dawn quite quickly. She was good at it and both of them were shouting for more. Jack had, so far, only been fucked by David, Mike, and now Steve, and had only ever given full anal to an old girlfriend, but he had been looking forward to fucking David, and was now going to get some practice on this beautiful woman.

Dawn quickly got into rhythm with Jack as he groped her cunt from below, and bit her back to make her wince. Steve came round to her front and Dawn took his cock fully down her throat. "Darling Steve, I want you up my cunt now so we're a proper threesome."

"Ok darling" said Steve. "Alice, can you stand up for a minute til I get under Dawn?"

Jack stood up. Dawn kissed him very deeply "Alice," she said I'm loving you screwing my arse. Now this is going to blow both our minds since you'll feel Steve's cock pounding inside my cunt, as your spearing me from above."

Dawn mounted Steve as he lay beneath her and Jack got back into position, now ramming her harder than ever. All three wanted it to go on for as long as possible, but Jack had been getting so excited, feeling this woman in her sexy nylon bodystocking, through his own sexy underskirt, and wanting to fuck her, til she screamed with pain and pleasure, that he had to cum.

As he screamed to the others, they both went as hard as they could for the countdown, then jets of semen exploded into Dawn, entering her ecstatic, shaking body, from above and below.

As cum leaked from Dawn's cunt, and asshole, Steve and Jack bent down to lick her clean, and all three kissed and licked each other til they fell exhausted on the bed, the two men worshipping Dawn's perfect body from the front and back.

The next day there were quite a lot of filthy pics circulating amongst the group, and there was a general feeling that Jack had excelled himself in looks, as Alice, and in performance in all positions.

Since Jack had not brought his own clothes Dawn had helped him get back into Alice's outfit. "Alice," she said, kissing Jack with a certain longing, "I wish I could just take you home with me."

Jack smiled, " I'm sure we'll see each other before long. It was bliss with you and Steve!"

Steve and Dawn dropped Jack back at David's house where David welcomed him back with a long embrace and a deep sensual kiss. "Jack," said David, "I want you so much. Can you come back tomorrow night, and I'll dress up for you. You can spend the night with me if you like."

"David, I want that more than anything. I'd love to and I can't wait to make love to you.