It had been a few weeks since Michaela had gone down on Jamie at the club, and Jamie had given him her telephone number. After a while she decided that Michaela must have had second thoughts or maybe had cold feet. Anyway, now that she and Frankie were regular lovers, it didn't really matter. Then one day when she was at home before going to work the telephone rang; it was Michaela. He sounded nervous, just like he had been at the club, starting off by apologising for not ringing earlier.

“I had to travel overseas but I'm back now and I wondered if I could take you up on your kind offer?” he said.

Jamie paused to think about it. What would Frankie think now that they were regular lovers? He had already gone out early to do some shopping first, so couldn't be asked, but then Jamie remembered what Frankie has said about having a threesome..

“The club is open seven nights a week, and Frankie and I work six of those nights. We'd have to work out a suitable time for us to get together. I get next month's rota in two days, could you ring back then and we'll fix a date?”

Michaela sounded disappointed. “Look, if you don't want to meet up, I'll undertand...” his voice trailed off.

“No, I'm happy to meet, it's just a question of fitting in with my rota,” said Jamie. He was really buying time, but Michaela didn't have to know that.

When he had a chance to chat with Frankie later at the nightclub, he told him about Michaela.

“How do you feel about me meeting up with him? I'm guessing he'll want to go down on me again.”

Frankie laughed. “Why should that be a problem? You do plenty more than that with the customers here.”

“Well, that's business, and since we started sleeping together, I thought, you know?”

Frankie smiled. “We're not married, Jamie, we can fuck who we like and still fuck each other. No, you go for it. In fact, if you can fix a time when we're both home, maybe we can make that threesome we talked about, with Michaela if he wants; you know, a bit of 'spit-roasting'.”

“OK, I'll ask him,” said Jamie, but he wondered if that was a step too far for Michaela at this stage. Jamie hadn't tried threesomes yet but he knew that Frankie had entertained two men at once in the bedrooms at the club. With that in mind, he organised a meeting day with Michaela when Frankie was working and he had a day off.

An opportunity came the following week and Jamie prepared to receive Michaela in the early evening. She dressed in sexy black lingerie, stockings and six-inch heels, and wore a silk dressing gown. The doorbell rang at precisely the arranged time of six o'clock, and after checking through the security window, Jamie let Michaela into the flat. Michaela still looked a bit nervous.

“I'm not too early am I?” he said, as he followed Jamie into the lounge room. Jamie sat on the couch letting her robe fall open, revealing her lingerie and stocking-clad legs.

“Wow, you look amazing!” gasped Michaela.

“Thank you,” said Jamie with a smile.

Michaela looked around the flat, admiring it. “Are you on your own?” he said.

“Yes, Frankie's working at the club tonight. He'll get back about two in the morning, assuming he comes home.”

Michaela blushed slightly at the implication of Jamie's words and Jamie changed the subject.

“So what are you wearing today under those boy clothes?

“I've only got one set of lingerie, I'm afraid. I bought it by mail order as I couldn't bring myself to go into one of those shops.”

Jamie laughed. “I guess they can be intimidating places. Before I started dressing fulltime I used to say I was buying lingerie for my wife. There's no problem now of course and even if the women there know I'm a tranny, my money is as good as anyone else's. Anyway, I was wondering if you'd like to put on some makeup this evening?”

Michaela's face brightened: “Oh yes!” he exclaimed. “I have to warn you I'm not much good at applying it.”

“That's alright, every girl has to learn how to apply makeup. How about I give you a lesson? Let's go into my bedroom and you can get undressed.”

Michaela followed Jamie into the bedroom and following Jamie's suggestion that he remove his outer garments to avoid getting makeup on them, he stripped down to reveal the lingerie he was wearing the last time Jamie had met him, a black lace bra and camisole, black satin panties, a suspender belt, and sheer black stockings. Reaching into a bag, he produced a black full slip with French lace on the bust and hem. Smiling shyly at Jamie he slipped it over his head and let it flow down his body.

“I brought some heels with me too,” he said, reaching into the bag and drawing out a pair of pumps with three-inch heels which he slipped on. “I bought them from a charity shop. I told the woman there it was for a fancy dress party. It was hard to find a pair my size but I did eventually.”

“You look gorgeous,” said Jamie. “Now I want you to go into the bathroom and give your face a good wash with soap and water. That way you remove any oils on your skin and it gives us a nice blank canvas to work on.”

Michaela did as she was told, and when she returned to the bedroom, Jamie told her to sit in front of the dressing table mirror and watch the process so she could do it herself next time.

“I'm only going to do basic makeup this time and we'll go on to more exotic looks next time,” Jamie said.

Michaela watched intently as Jamie applied foundation and concealer, followed by a little eye shadow, explaining that she wouldn't do mascara and eyeliner this time. She added some blusher to Michaela's cheeks, and the final stages were to apply lipstick and then setting powder. After that, Jamie set about brushing Michaela's hair which was now noticeably longer than it had been the last time Jamie had seen her.

“There! What do you think?” said Jamie. Michaela was speechless as she stared into the mirror. When she finally found her voice, she said: “I can hardly believe that's me.”

Jamie laughed. “I felt the same way the first time Frankie did my makeup. One of these days you'll be passing on your skills to someone else; that's how it goes.”

“Thank you so much,” said Michaela. “I feel like crying.”

“Don't do that, it'll ruin your makeup,” said Jamie with a laugh. “Now why don't you stand up? Did you know, you have very kissable lips?.”

Michaela stood up and faced Jamie. Her heart was pounding as she knew what was coming next. Jamie drew her closer and they began to kiss, gently at first and then their lips parted and their tongues began to play, curling over and under and their teeth grinding against each other's.. Their bodies were now pressed against each other, and both could feel their erections growing.

“Let''s get on the bed,” murmured Jamie. As they lay there, enjoying the feeling of two bodies clad in silky lingerie sliding against each other, Jamie reached down and began to fondle Michaela's erection through her panties, and taking the hint, Michaela responded in kind.

“Oh my! It's like we're two women enjoying each other,” she whispered. “It's lovely.”

“Why don't we 'sixty-nine'? Then it will be even more like two women do,” said Jamie.

“Oh yes please,” responded Michaela, and Jamie quickly turned around. They both started to suck each other through their panties and then Jamie freed Michaela from the satin and began to lick and suck her. Michaela followed suit and they both set to work to bring each other to a climax. Jamie, being more experienced, held back until she knew that Michaela was about to erupt into her mouth and as it happened, so she let go and filled Michaela's eager mouth. They both swallowed the warm semen and licked each other clean before Jamie reversed her position once more and they lay together kissing and tasting the traces of their own semen in each other's mouths.

“That was so lovely,” murmured Michaela.

They lay there together for a while but it wasn't too long before they began to get aroused again.

“Have you ever been fucked?” said Jamie, already knowing the answer.

“No, I'd like to but I've heard that it hurts, so I'm afraid to try it,” said Michaela.

“Well that's not necessarily so; have you ever heard of something called 'poppers'?” said Jamie. Michaela hadn't, so Jamie explained how it relaxes the anal sphincter.

“Frankie got me to use it when she took my virginity, and it didn't hurt at all. If you'd like to try it, I promise I'll stop if you ask me to. What do you think?”

Michaela stared at Jamie. “I trust you Jamie, and if there's anyone I'd like to take my virginity, it's you,” she said.

“Since you trust me, I suggest that I don't use a condom since I am regularly tested and I'm certain you will enjoy it more when I come inside you. Now get on your hands and knees on the bed with your head facing away from me, and we'll begin.”

Michaela did as she was told. Jamie raised her slip and pulled down her panties to expose the twin orbs of her bottom, all the while explaining what she was doing. Michaela's bottom quivered but whether from fear or excitement or maybe both, it was impossible to tell. Jamie explained that she was putting plenty of lube on her own organ, and then started to fill Michaela's crack with plenty more. As her fingers explored Michaela, her bottom quivered even more and she let out a quiet groan.

Jamie told her to take a few deep sniffs from the 'poppers' bottle and say how she felt.

“Oh, I feel like I'm floating,” gasped Michaela as she settled down on her hands and knees once more. Jamie smiled as she moved forward. That was what she wanted to hear. “Now relax and enjoy,” she said as she pressed the tip of her erection against Michaela's anal bud and as she expected, the pressure caused it to give way. As she slid inside Michaela, she heard her gasp. “Oh my! That feels so good, Jamie.”

Jamie held Michaela's thighs and slid the whole length of her shaft deep inside her and slowly started to pump. Michaela was moaning with pleasure.

“Oh Jamie, that feels incredible. You're going to make me come.”

“Not yet, Michaela, let's just enjoy it,” said Jamie as she slid her organ in deep and then withdrew it most of the way before burying her shaft deep into Michaela once more. Michaela continued to moan and gasp.

“Fuck me, Jamie, I'm yours! Oh, it feels so good,” she cried between moans.
Jamie reached around and finding Michaela's erection wrapped her fingers around it and began to milk her which made Michaela's squeals of pleasure even louder. They continued this way for a few more minutes until Jamie sensed that Michaela was not far off climaxing. She increased the speed of her thrusts, feeling Michaela press back against her to take her whole shaft inside. Jamie was now moaning too as she enjoyed the feeling of Michaela's velvet tunnel wrapped around her erection. She was no longer trying to hold back, and as she felt Michaela's erection convulsing and the sticky semen on her fingers, she climaxed too and poured herself in hot jets deep inside Michaela whose squeals of pleasure were probably audible in the street.

For a few moments, they stayed locked together, panting and gasping for breath before Michaela slowly collapsed on the bed, with Jamie on top of her. They lay in that position for some minutes until Jamie softened and slipped out of Michaela. Then they curled up against each other and gradually dropped off to sleep.

When they awake, Michaela asked Jamie what had happened. “When you first entered me I felt full. Then when you went in deeper I suddenly began to feel something incredible. I know I was going to come and I couldn't stop it, in fact, I didn't want to stop it. What happened?”

Jamie smiled. “That's why males enjoy anal sex in a way women can't. I was stimulating your prostate with the tip of my penis and that made you want to come.”

“Well it was much better than masturbating,” She paused. “Can we do it again please?”

“It will be my pleasure,” said Jamie, “And yours too.”

Frankie arrived back at the flat at about three o'clock. She'd had a tiring but lucrative night at the club. She was already getting a small group of admirers whose wives refused to do what they wanted, and as a consequence, she had had oral sex with two men and anal sex with three others. She certainly had no desire for more sex that night but felt she should check on Jamie, so she tapped lightly on her door, and when there was no answer, quietly opened it. Seeing the two figures spooning on the bed and the smell of semen in the air, she smiled to herself and quietly closed the door again. Going to her room she undressed, took off her makeup and putting on a nightdress, got into bed and in a few minutes was fast asleep.

To be continued

Next time: Michaela's education continues