MY BROTHER, MY SISTER
by Jenny Bowman
Copyright Jenny Bowman 2001
Chapter 3
The following week was an anticlimax - no pun intended.
I was still a bit, ummmm, excited even though my climax on Sunday night had been unbelievable. My fingers, and my clit got a bit of a workout during the week and I tried out the vibrator that Helen had bought me. Wow..... Better late than never!
Brad was apparently feeling the strain too, because a couple of times, when mum and dad were not around, he said things like "I wish I could wear Sally's clothes tonight" or "I wish Saturday was here so we could play our games again". Obviously the weights hadn't been a problem. I wondered if Helen would buy heavier ones.
I got a phone call from Helen one night. She said "I know your mum and dad are probably there and I know you can't talk, so I'll tell you what I found out".
Apparently she'd been talking at work with some of her girlfriends and the conversation got around to the male anatomy, then specifically to the prostate. She told me where in the body it was and then said that, if it's massaged, the sensation for the male is much like coming, except they don't!
"You remember I told you I wanted to play with a guys balls and see if I could get him to come without stroking his dick? Maybe this will help. And maybe his balls will just fill and fill and fill and can you imagine how much cream there'd be when he finally came?"
I could. I could also see that Sally was in for an interesting time when next she saw Helen. Or, come to think about it, me.
I had also been able to make a couple of phone calls to check out women's shoe shops and their acceptance of crossdressers or transvestites.
By the time Saturday came, I don't know who was the most excited; Brad, Sally or me.
Mum and dad had an early start, 0630, and were barely out the door when Brad asked me if Sally should join us. I told him I didn't know and went on:
"I checked some shoe shops during the week and a couple are OK about serving crossdressers. In fact the lady who owns the one next to the coffee lounge at the mall said she opens early or stays late for her 'special girls'. Her words." Sally smiled. "So if you want to try and get some pink shoes to match the dress, as long as we're at the shop by 7.45am and out by 8.30am Sally can go shopping with me. Otherwise...."
I don't think I'd ever seen Brad smile so much. As he left the room I said "And we can park right outside so don't worry about shoes. Just wear the ones of mine you had on last weekend".
We didn't have a lot of time to get ready but by the time we were ready to leave, Sally looked truly scrumptious. I thought, if I was a guy, I couldn't keep my hands off her.
She was dressed in everything we bought the previous weekend. There were only two things that well, didn't exactly spoil the effect, but certainly could be improved. And when we were in the car Sally mentioned them both herself.
"I think I should get a pair of high heels that fit me and show off my legs....." she grinned ".... and the sooner my hair grows, the happier I'll be".
I agreed; the shoes she was wearing - my shoes - were OK, but they could have been better. I also noticed that the hair on her arms needed dying, or bleaching.
"Do you think I could pass as a woman, Jen? After we get the shoes, I mean"
I looked her over critically. "Yes, I do think you could pass just walking along the street, but as soon as you started talking, the other person would pick you straight away. That's something you will have to work on."
Sally smiled. "Yes, I thought you'd say that" she breathed. I was amazed.
"Say something else, just the way you said that".
"You mean you want me to talk like this? Keep my voice smokey?"
Smokey? I didn't know what she meant, but she sounded fabulous. If I didn't know......
"I've been practising all week whenever I got a chance. What do you think?"
"What do I think? If I was a guy I'd cream my jeans!" and then realised what I'd said.
"Why Jen, I do believe you're jealous" Sally said.
I laughed. "Just make sure you don't steal my boyfriends!"
By the time we reached the shoe shop Sally was quite excited, certainly because she was buying shoes dressed as a woman but I think more so because she wanted to see if she could pass. It probably wasn't a good test because the shop owner knew that Sally was a crossdresser but I suppose for Sally she had reached a milestone.
Virginia - Ginny - opened the door - we'd exchanged names on the phone - and I could see she was confused. She looked at both of us in turn, backwards and forwards a couple of times then said "Is your special friend coming?"
Sally and I looked at each other and giggled. "I'm Sally" she said "and this is Jenny. You and she spoke on the phone."
"But is your special friend coming? The... ah..."
"I'm the special friend" Sally said. "I'm truly sorry if I've embarrassed you but I wanted to see if I could pass, especially after I spoke. I guess I can".
"You certainly can. Wow. So how can I help you?" Ginny asked as she led us inside the shop.
As Sally and I sat, Sally told her what she wanted. "OK. Let me check you shoe size then I'll see if I've got anything in pink or white".
While she was in the racks I noticed she also had a small range of handbags that would look nice for Sally, depending on the color of the shoes.
As she came back to us with boxes of shoes I could see Ginny shaking her head slightly. "I can't believe how good you look" she said as she sat. "You'd pass anywhere. Except for that" she said, and smiled.
I saw where she was looking and realised that Sally was waiting to try on the shoes with her leg up so that Ginny could see straight up her dress.
Sally was embarrassed. "I'm sorry, I didn't....."
"Oh, no that's OK. I don't mind looking at clits that size. Um, it is OK to call it a clit, isn't it?"
"I guess so" Sally said.
"Can I.... ah.... you know.... as a reward for opening early.... um...."
Sally pulled her dress back to reveal her panties with part of her di... clit poking out.
"I.... uh...."
"Of course you can".
I thought I'd better join the conversation. "But don't forget we have to be out of the shop by 8.30".
"Ah, that's OK. Sally can pass so you can stay a bit longer. Besides I don't think I'm going to be inundated with customers right on nine o'clock". Ginny reached out and with trembling hands touched Sally's di... clit.
Sally jumped, then sucked in her breath as Ginny stroked along the length of it. I noticed that Sally had worn the cock and ball strap.
"I haven't felt one of these for soooo long I'd almost forgotten what they felt like. My God, it feels so wonderful. And your balls, tied up in a parcel. Are they for me? Can I keep the shop closed.....?" she joked.
By now she had put the boxes down and was using both hands, one on Sally's clit and one on her balls. Sally's excitement was obvious.
"Oh God, I hope you don't mind" Ginny said to me. "I didn't think.... I just...."
Ginny was obviously unsure of my relationship with Sally, but I noticed she was still stroking; she wasn't going to give up too easily.
"It's OK". I said. "I'll get my share this afternoon. But you can't let Sally come. She's learning how to control herself as young girls do. And besides, there'll be more cream for Sally and me this afternoon."
"Sally.....??"
"Yes. She's learning to enjoy it so that when she goes on a date.....".
"Oh, lucky Sally. I was hoping...."
"Maybe next time. I know Sally will need more shoes in the future. And talking of which. We really must go soon, we've got a lot of things to do so....."
Ginny reluctantly stopped her work on Sally's clit and balls and got to work selling Sally some shoes. I mentioned the handbags and Ginny brought them over. I must say they suited Sally perfectly; slingbacks in a pink with white toes and matching handbag.
The only thing that was still wrong was Sally's hair and by next weekend I thought it would be ready for a visit to the hairdresser.
On the way home I brought up something I'd been thinking about all week - Brad's, Sally's future.
"I've been thinking of where you should go from here" I said.
"What do you mean?"
"Well.... present appearances notwithstanding, you're really a guy and under normal circumstances you'd dress like a guy, take out women, probably get married and have kids and so on. From the way you're dressed these are obviously not normal circumstances. So I think you've got to make some decisions. I see the future for you as being several choices. First, you can treat this past week as an enjoyable fantasy and go back to being a normal guy. In which case all the control that we've been teaching you will come in quite handy. You'll be able to pleasure you're partner for quite a long time without the risk of going off too soon yourself.
"Second, you can be a guy who crossdresses occasionally, or frequently, just for your own enjoyment. If you do that, and you meet someone you get serious about you'll have to decide whether or not to tell her of your - ah - hobby. If you do tell her she may or may not accept it.
"If she doesn't accept it, you've maybe lost a soulmate. If she does accept it, one of two things might happen; first she'll help you with your clothes and make-up just as I've been doing and maybe you'll go out together as two girlfriends. The problem with that is that because you look so much like a real girl, you might get guys hitting on you and how would your relationship with your girlfriend - or wife - be then? The other thing that might happen is that.... I've noticed a couple of time that you've called Helen and me "mistress" so it's possible that your girlfriend might decide she wants to play games where she's the mistress and you're the slave. Which is OK if it's just the two of you, but what happens if she wants to share you with her girlfriends?"
By now Sally was looking at me with interest. I went on.
"For example she might want you to dress as a French maid with an apron and cap, stockings and high heels and no nickers and serve her girlfriends afternoon tea. The problem with that is that, because they'll see from behind that you have nothing underneath the apron, you can bet someone will want to see what's under the front. From there, anything goes. Someone will probably ask, apart from being a wonderful waitress what other services you perform and then you'll probably have to perform those services; maybe licking them to climax, and not just one but all, maybe stroking yourself, and you can bet that some will want to watch you come and some will want you to stroke and not come and maybe some will want to put on a strap-on cock and..... Well, you get the picture.
"You might also decide you want to live full-time as a woman in which case you'll need to take hormones to increase your bust, actually to give you a bust and then you'll have to decide if you want to take lovers. Male lovers.
"And finally if you decide to live full time as a woman you'll need to decide if you want to go all the way and have surgery, in which case you'll lose that wonderful cock and those beautiful balls and be given a vagina and once you go that route there's no going back.
"But whatever you decide, I'll keep on playing with you as long as you want me to. And Helen too, if you wish. In fact, I think Helen fancies you. Maybe you and she could get together, because she accepts what's going on. Anyway, we'll tease you to help you learn not to come too early, in fact not to come at all, just enjoy your body. You'll be pretty horny, but imagine what it will be like when you finally do come.
"If you decide to live as a woman or become a woman, Dad might be a problem, but I'm pretty sure mum will be OK. But whatever you decide, I'll support you all the way. It's kind of groovy to have a sister after all these years, but if you want to be my brother that's OK too. Obviously this is something you need to think about. You don't want to take two minutes to make a decision that could change your life."
There was silence in the car, and as we parked in our driveway the silence continued.
We were having a late breakfast, with not a lot of conversation when the front door bell rang. Sally nearly jumped through the window. "God, I'll have to hide. Who is it?"
"Relax, Sal" I said. "It's OK. I know who it is. Anyway, after the way Ginny accepted you this morning, it's safe to stay as you are. In fact, why don't you answer the door?"
She looked at me.
"It is OK" I said. "I wouldn't put you in a bad situation. Promise".
She seemed satisfied so she opened the front door.
The woman there was startled. "Oh, I'm sorry. I must have the wrong address. I thought Jenny and Brad lived...... Um...."
She seemed confused.
"Is that you Bra... um... Sally?"
"Yes" Sally said and giggled. "Come on in Barbara".
After we had laughed about Barbara's confusion and Barbara had relaxed I brought up the reason for her visit.
"Are you ready for the stick and ball game, Barb?"
Sally looked confused, then the penny dropped.
"Would you like me to change?" she asked.
"No. Just take your dress off and go and lie down on your bed. We'll come in, in a minute. Oh, and put on the cock ring and strap."
By the time we went into Sally's bedroom I could see she was already aroused; she was lying down as she was told, but there was a distinct bulge in her panties.
"I've been looking forward to this all week. How do we begin? Are there any rules?"
"No rules. Sally's happy with anything you want to do. Well, there are a couple of tiny rules. This is mainly about teasing and training Sally not to cream. She can cream, but not until we say so. And she can play with herself, but only on our instructions and when we say stop, she must stop otherwise she gets punished. You've got to watch her, because given half a chance, she'll cream".
"What sort of punishment?"
"Well.... I haven't really worked that out yet, but I do have a ball whip, so maybe, if she's bad, we'll whip her balls and dick".
Barbara's eyes glistened. "Yeah.... We'll have to be careful though. Sally might like it and be bad so she can get punished!"
Barbara's eyes were open wide, and she was panting very lightly in anticipation. Her hands moved towards Sally's clit and brushed it lightly through the panties. Sally jumped and sucked in her breath. "Seems like she's been looking forward to this too", Barbara said.
She continued to brush Sally's clit, and balls through the panties. I think she realised how tight and compact Sally's balls were because she had started to really get a grip on Sal's balls.
"This is so good" she said.
"Yes, it is, isn't it?"
"Aren't you going to join in?"
"Yes, but I'm going to play with Sally's breasts. You continue to work on her balls and clit. And take her panties off when you want to. Sally won't mind, will you Sal?"
"Noooooooooo".
I had undone Sally's bra and had started lightly stroking her nipples, using my nails to increase the sensation. By now, with Barbara's ministrations on her cock and balls, Sally was starting to moan quite heavily. She was obviously enjoying herself.
Barbara decided she wanted to get properly to her toys so she started working Sally's panties off. Inside the straps Sally's cock and balls were quite swollen. I hadn't seen them looking better.
"Her balls are so good to touch" Barbara said. "Bald and tight. In future I'm going to make sure that every man I see has bald balls and wears one of these straps all the time. All the time" she emphasised.
I couldn't agree more. Although I hadn't touched them inside their confinement, they certainly looked good enough to.... ah.... eat. And so did Sally's cock. I reached out and touched it. I couldn't resist. I just had to stroke it.
With Barbara working on Sally's balls and me on Sally's clit I knew it wouldn't be long before Sally would want to cream, and that wasn't going to happen. Yet.
I slowed my hand right down and suggested to Barbara she do the same. Sally's excitement seemed to increase. It must have been the strap. Reluctantly I stopped playing with her cock and went back to her nipples.
"Would you like to show Barbara how you stroke your cock. Sally?"
Sally's right hand went to her cock while Barbara continued to play with Sally's balls.
"Oh, that feels sooooooo goood" Sally whimpered.
"Not too fast. In fact slow down so that your hand is only just moving".
"Ohhhh"
"Slowly... slowly.... that's better. And if you continue to do it like that, maybe Barbara will let you go faster. But not yet".
Barbara was fascinated watching Sally's hand move so slowly. Or maybe she was fascinated watching Sally's cock being stroked by Sally and wanting to do it herself. Whatever it was, she seemed mesmerised.
I was continuing to play with Sally's nipples and Barbara was working on Sally's balls; every time I looked at them they seemed bigger. I guess it was the effect of the strap. And Sally's clit looked like it might explode.
Then Barbara said "Sally, you're going too fast". I looked over. Sally's hand was almost not moving. Too fast?
"Stop" Barbara commanded. And instantly Sally's hand stopped, as much, I think by the tone of voice as by what had been said.
"You were told to only do it slowly and you disobeyed so now you're going to be punished. Give me the whip, Jen".
I couldn't believe my ears. As I passed her the whip, Barbara winked at me.
"This is for being a bad girl and not doing what you were told".
And with that, she whipped Sally's dick. The strands of the whip were only about four inches long but when they hit Sally she jumped. The couldn't have done much more than sting, but when she heard the word 'whip' I'm sure Sally thought she was going to get whipped by a cat o' nine tails.
Barbara hit her again. And again. And then on the balls.
By now Sally's dick was dripping and she was panting, not from pain, but from excitement.
"If I stop whipping you, will you be a good girl and stroke yourself slowly?"
"Oooooohhhhhh"
"Sally?"
"Yes, mistress. I'll be a good girl and stroke myself slowly".
There was that word again.
"Well see that you do. You may begin".
"Thank you mistress" and with that Sally began again. Slowly, very slowly. I was sure she would have liked the whip again but I was equally sure she wasn't brave enough - yet - to be so blatantly disobedient that she'd get it. But I was sure that time would come.
I looked at my watch. We'd been playing with Sally for about two hours and, with a little bit of help from us, she'd been able to control herself and not come.
I motioned to Barbara and showed her the time. She was amazed. "I have to go in about five minutes and I was so wanting to see her come. But I understand why not. Maybe you'll invite me again and next time....?"
I was about to answer when sally said "Jen, I want to come, I need to come, can I come so Barbara can watch? Please?"
"No Sally, you can't. As Barbara said, next time. And Barbara has to go now so you'll have to stop playing with yourself and get dressed to that you can say goodbye to your guest at the door".
At that Sally started to pump again, fast, hoping I suppose to come so fast it would be over before we were aware of what was happening. She was wrong. I was waiting for that to happen and I slapped her hand away. "No" I said.
She whimpered and stopped playing with herself and reluctantly sat up. Looking at Barbara she said "That was absolutely wonderful. Your hands.... I'm in love with your hands".
"Why thank you Miss Sally" Barbara said and looked at me. She raised an eyebrow.
"Should we let Sally dress in private?"
"I suppose so. Every girl must have her secrets. Don't forget to touch up your makeup. And leave your cock and ball strap on. You might need it again this afternoon. We'll wait for you in the lounge room. And don't touch your dick. I'll know if you do and you'll be in trouble. And if you think I'm bluffing.....". And with that we left Sally to repair the disarray to her clothes and face.
Ten minutes later she joined us and Barbara left us with a promise to come again for another bat and ball game and next time score a home run.
Lunch was a quiet affair. I think Sally was still exhausted from the morning's activities and I think she was also thinking about what I had said about her future. And there was also my comment that she might need the cock and ball strap this afternoon. What she didn't know, and I wasn't going to tell her, was that Helen was coming over to try out the technique with Sally's prostate, first with her fingers, to identify where it was, and then with the vibrator. I thought the vibrator on its own would certainly warm up Sally, but when the vibrator was working on her prostate I wasn't sure what would happen.
We'd just started talking about buying some more dresses and perhaps a suit and getting Sally's hair done next weekend when the door bell rang again.
This time there was no hesitation; Sally went straight to the door to open it. I hate to think what she would have done if it had been mum and dad returning early, but it was Helen.
I could see Sally's face light up in enjoyment. Now she knew why I had suggested she leave on the cock and ball strap.
After our greetings, Helen asked "Have you been a good girl this week, Sally? No surprises, no sticky beds when you woke up in the morning?"
"No, nothing like that. Until this morning when I woke, I haven't touched my clit all week except when I showered or had to pee".
Helen looked at me and mouthed "Clit?" I shrugged. Whatever Sally wanted to call it was OK by me.
"Well, Sal. If you've been that good, maybe Jenny and I will let you come this afternoon. What do you think, Jen?"
"Yeah, I think so. She was naughty this morning and wouldn't stop stroking herself when she was told but she was whipped on the co... er clit and balls for that so I think she should be rewarded for being a good girl all week. Shall we adjourn?"
Once again Sally was in her underwear lying on her bed when Helen and I walked in. Helen immediately saw the bulge in Sally's panties caused by the strap swelling her clit and balls.
Helen reached for the bulge and squeezed. "Fantastic" she said. "They feel exactly the way the salesperson in the sex shop told me they'd feel. Tight and hard". And with that she got to work while I, once again, started work on Sally's breasts.
Instantly she was hard and within minutes she was moaning and starting to buck.
"We had a session this morning...." I told Helen ".... which is probably the reason she's so excited."
"Means we don't have to work so hard. Would you like to have a stroke, Sal? Show us how good a cock stroker you are? After all, if you stay a girl you'll have to do a lot of that."
"I think I'd like that" Sally said, as she started stroking her clit. That was interesting. Did she mean she'd like to stroke her clit or she'd like to stay a girl and stroke guys dicks?
Whatever she meant, she was doing it slowly, I noted. Maybe she'd learned her lesson this morning. Or maybe she remembered my comment this morning about Helen fancying her and she was putting on a good how for Helen. But whatever the reason, she was putting on a good show.
As was Helen, who was bouncing Sally's balls in her hands.
"Sal, I want you to roll over and get on your knees so Jen can milk you".
While Sally was turning I noticed that Helen had taken from her bag a tube of lubricant and was putting on one hand a rubber glove. As Sally got onto her hands and knees I put my hand under and started slowly working on her clit. I noticed that Helen was lightly stroking Sally's back and bum, gradually sneaking a finger or two between Sally's cheeks. Sally had really started to moan and was thrusting backwards and forwards, trying to increase the speed of my hand and, at the same time, trying to impale herself on Helen's fingers. As Helen's fingers opened Sally's cheeks, she squeezed the tube around Sally's opening and started to massage in the contents of the tube. I was fascinated by what was going on, so much that my hand was almost still. But that didn't matter, because Sally was still moving her clit in my hand.
I watched Helen start to insert a finger and move it back and forth, into then out of Sally. Sally was now moaning loudly and breathing quickly in short gulps. The finger was moving in and out, in and out and Sally was pushing herself onto it and it was buried deep inside Sally and then Helen inserted another finger and now there were two inside Sally, moving, moving, never still, massaging her, letting her feel, if only in a small way, what it would feel like to be a woman, with a man buried deep inside her. And still Sally moved on Helen's fingers and then I saw Helen change her position and thrust deeper inside Sally and Sally yelped and started to pump and my hand was wet but Sally hadn't yet come and I knew that Helen had found her goal, had found Sally's prostate. Helen continued to massage the prostate, filling Sally's balls and I remembered Helen's wish to see if she could get a guy to come without stroking his dick. But what, now, was Sally? Was she still really Brad, or was she now enjoying the deepness that only a woman can enjoy?
Helen motioned for me to pass her the vibrator and as she started to remove her fingers, Sally was saying "No, no, don't stop, I want to come with your cock inside me, oh fuck me, fuck me....." but Helen continued to remove her fingers and then she turned on the vibrator and replaced her fingers with the vibrator and pushed it into Sally's hole and brought it out and pushed it and out and in and.... and by now Sally was really bucking and I could see Helen was searching with the end of the vibrator for Sally's prostate and then Sally yelped again and I knew that, once again, Helen had found her goal. I knew, too, that, although she hadn't told me, she planned on massaging Sally's prostate for some time. How long was "some time?" I had no idea, but knowing Helen, I wouldn't have been surprised if it had been a year!
I checked underneath Sally. Her clit was absolutely flowing and I didn't think she could last much longer. Obviously Helen didn't think so either because she left the vibrator inside Sally and went and get the measuring jug and placed it under Sally's cock. Then she started working the vibrator again and I decided I should start again properly on Sally's cock and to make up for missing out this morning I also worked on her balls, squeezing and stroking, slowly, then a little faster then faster still then slow again then fast while Helen worked the vibrator on Sally's prostate, both of us controlling her, bringing her on then taking her away, then bringing her on again then taking her away, all the while Sally working her body, plunging deep into my hand, then rising high onto the vibrator, all the while moaning, yelping, gasping for breath and then I could feel her cock tightening, tightening as the muscles contracted and she was coming, spurting, flowing, overflowing into the measuring jug, pumping, pumping, gasping, pumping then slowly, ever so slowly slowing, but still flowing, still coming and slowly, slowly and then finally falling sideways, exhausted onto her bed. But still the vibrator was inside her and still she leaked and then Helen, perhaps taking pity on her, turned it off and slowly, gently removed it from our tired and exhausted Sally.
I lifted the jug so Helen could see the quantity and then we started to feed Sally her reward. She sucked our fingers greedily then said, quietly "I want it all. Give me the jug" and we did and she drank it all and said "Isn't there any more? I want some more. Will you stroke me again I want some more cream" and started to work her dick herself.
We lay alongside her, one in front, the other behind and petted her and calmed her and gentled her and gently and gently and soon she was asleep, resting, recovering.
We left her in her bed and went outside, stunned, because of the quantity of cream the three of us had produced and because of Sally's final reaction. When the time finally came for her to choose her future, I thought I knew what it would be. And it wouldn't be surgery.
From then on, every weekend Brad became Sally and usually she and I went shopping and then, when we come home, Sally and I played. Helen joined us most weekends but sometimes it was another girl or woman, someone we met while we were buying clothes for Sal.
Four months later Brad suggested it was time he and I moved into a flat of our own. He wanted to spend more time as Sally and he also realised that, with summer coming, if he was to continue waxing his legs, mum and dad would want to know what was going on.
Soon after we moved, we helped Margo train Ron to become Julie and from that we started a regular training course for women who wanted more from their men.... and you can take that any way you wish! We advertised the course as "Everything you wanted to know about men but were afraid to do!"
Margo and Julie started to go out to nightclubs and such and, as would be expected, were soon being chatted up by guys. Although both said "No", Margo suspected that Julie really would like to take a male lover so she decided to give Julie a very special birthday present.
James, one of Margo's workmates had been asking to take her out but she always declined saying "I'm married". James reply was always "That's OK, so am I". But finally Margo relented when she discovered James had a friend, Alan, who was bi-sexual.
Margo and James arranged to meet at a club, Margo to bring Julie and James to bring Alan.
Consequently James and Alan approached Margo and Julie at the club. Several hours later, after dinner and dancing, the men suggested they leave. Margo turned to Julie and said "Would you like Alan to take you home? I'd like to go with James".
Margo didn't tell me what Julie said when she learned her wife wanted to go home with another guy but apparently it didn't matter too much because Julie wanted to go home with Alan.
The following day Margo and Ron discussed the previous night and Ron revealed Julie was no longer a virgin. Margo hadn't slept with James but was happy for Julie's success. Now Margo and Julie regularly double date and Margo sometimes sleeps with another guy but usually she and the guy both enjoy Julie, Margo riding Julie's tongue and the guy riding Julie or sometimes Margo riding the guys tongue and Julie giving the guy fellatio. Margo, Ron and Julie are, apparently, excessively happy with the arrangement.
Sally and I advertised our course as being conducted by Jennifer and Brad and Sally but when class starts only Sal and I are in front of the class. Invariably someone asks when Brad is arriving and we always say "Be patient and all will be revealed".
The class always starts with the "students" seated and when Brad is revealed, excitement grows.
Then Brad lies on a portable massage table and Brad and Sally and I demonstrate our special training techniques. Then we invite the participants to join us at the table and there is always a scramble to get the premier position - alongside Sally's cock and balls. There are always eager participants, wanting to get hands on experience with Bra.... Sal before going home to their men. In fact, on one or two occasions some of the class have almost come to blows saying it was "...my turn to stroke her cock...", ".... no it's not, it's my turn...." Some of the class were, apparently, a little bit needy!!
The ball strap and weights are quite a feature with Sally now able to carry almost three times as much weight as the first time. And my how they swing around when the class members enjoy their hands on work.
Nowadays Brad lives as Brad during the week and nights and weekends as Sally. Brad told me that he'd like to live full time as Sally but two things are stopping him - first, mum and dad's reaction and second, his occupation. He said he isn't ready to tell his workmates of his desire to be Sally and he isn't yet ready to change company's so he could start a new job as Sally. I guess time will tell.
Helen joins us most weekends and frequently she rides Sally's cock while I ride Sally's tongue. Helen confided to me that she plans to buy a strap on dildo to use on Sally instead of the vibrator. Apparently it was Sally's idea! I haven't yet ridden Sally's cock because she is, after all, still my brother. And I don't think I ever will. Although....
Sally and I occasionally double date but she isn't keen to date on her own because she hasn't yet decided whether to stay a guy or have SRS and she isn't sure what she would do if a guy really put the hard word on her.
That's what she says. What I think is really happening is that Sally and Helen are getting closer and closer. They frequently date, sometimes Helen going with Sally and sometimes Brad. But when they come back to the flat - which isn't very often, mostly they go to Helen's place - I can hear both their voices raised in pleasure. Helen obviously doesn't mind having a boyfriend who's a cross dresser. Boyfriend? Yes, I think so and, in fact, I wouldn't be surprised if Brad and Sally soon move in with Helen. That will probably mean that I won't be able to enjoy Sally anymore except in class, and probably not even then because the students will have priority. But that's OK. The world is full of well hung guys waiting to be trained. Although they don't yet know it!
I don't think Sally will have surgery, but I suggested she think about either taking hormones or having breast implants because, if she decides to become Sally full time, she's halfway there. The only problems that I can see are that with hormones, the more estrogen or progesterone that's pumped into the male body the less chance there is for the male to get and keep an erection. I have read recently that Viagra helps, to a certain extent, to reverse the effects of the female hormones, although only for an hour or so. With breast implants there's nothing, that I know of, that's safe. Except maybe saline. Apparently there are a couple of female Doctors near us who advise transvestites and transsexuals so I think Sally will see one of them. I'm happy about her seeing one of these Doctors because in my experience females are much more accepting than men of cross dressers and transvestites.
Of course if Sally decides to go back to being Brad, can you can imagine what a fine time she will have when her girlfriend - or wife, and the way things are going it will be Helen - discovers she has breasts. If I was in that situation and my man had breasts, you'd never get me out of bed. But I would want an active cock too. But a guy with breasts.... Yeeeeesssssssss!!! I think Helen would agree. I also think that Helen would accept it if Sally wanted to take a male lover. I don't think she'd be ecstatic, but she would accept it.
I've helped all my boyfriends go through almost all of what I helped Brad go through and, one way or another, they've all benefited from it. And they all look great in a dress. If you doubt it, you should try it sometime. Most haven't wanted to live full time as women but have been quite happy to be women for a couple of hours a week. But there have been a couple I know have decided to make the change. I'm so pleased I helped them make the decision.
We've also started another other training school, this one for milkmaids. Brad really loves this class.
I started to smile.
"Jen. Jen".
"Wha... wha....?"
"Jenny. Are you alright?"
I became aware of where I was - sitting in a restaurant having lunch with Megan. I also became aware I was smiling and that I'd sprayed coffee all over the table.
"What? Oh, yes. I'm alright. I was just thinking of something. Yes, yes I'm fine".
I looked across the room at a guy sitting by himself. I started wondering what he'd look like in black lingerie and a black cocktail dress with a ribbon around his balls and another around his dick, waiting for me to pick him up to take him out for dinner. I smiled some more and he rose to come and talk to us.
Men are so easy.