Elaine & Me


I looked into her eyes and drew her close and gave her a cuddle and a kiss on her bare shoulder. "I want you take off your panties and bra now. Let me see what you look like," I whispered in her ear.

"OK," and she stood back sniffing back the tears but still steady in her skyscraper heels.

The bra was quickly detached and she handed it to me and I noted it had a 36C-cup size on the back. It was lacy and had a silky texture and it was warm and smelled of her perfume.

She started tugging at her tight fitting panties that fitted her wide hips so well. Apart from the lack of pubic hair that was still growing back and some bruising, it looked like a female vulva. She spun round and I was sure I was looking a beautiful woman. There was no body hair anywhere apart from that stubble at her crotch while her legs seemed to go on forever.

"I'm still a little tender down there but the doctor has said that very gentle intercourse is possible. Do you want to try?" she asked.

"No not yet, I'm still coming to terms with what you have told me. Obviously the first thing that drew me towards you was your physical appearance. I thought you were gorgeous when I first saw you in that pub. Obviously this revelation changes things slightly. I mean as a former man we can't get married or you can't conceive. I would have liked to marry you and start a family. Now I don't see how we can." I said looking at her she started to put her clothes back on. Finally I added, "You must know that you are the most gorgeous creature that I have ever met."

"There are ways around all of those problems," she declared. "We can get legally married abroad. Several countries allow transsexuals to marry and Lorraine has agreed to help us with the conception and birth of a child. If you do decide to continue, you will in effect be marrying both of us."

"You talk of marriage as though it is still something that is possible. I'm sorry Elaine this has knocked the wind out of sails and it will take time to adjust. I would like to start again and see what develops. We are both young and there is plenty of time."

"Does that mean that you still want to have a relationship with me?" she asked with her usual pouting lips staring at me.

I took my time and paced about the room with two pairs of eyes watching my every move. I walked back to the window and looked out again, my dreams had been shattered but I was still captivated and fascinated by her. Most of all I really loved her. This was going to be difficult then I spoke. “I need time, to think about this, OK. I think I would like to have some time by myself now.”

I walked through to the hall and Elaine followed me like a lost little lamb pulling on her top clothes. I got my jacket and put it on and with one last despairing look from her, I said goodbye.

As I went through the door, I put my hands in my pockets and trudged up the drive. About half way up I looked back, half expecting her to be standing in the doorway. However the door was closed and I could just imagine (or I hoped I could imagine) the tears that were being shed inside instead.

Instead of walking home, for some reason I found myself turning right. Perhaps it was because I knew that it would bring me back past the gates to her house again that I went that way.

Anyway I didn’t know what to think anymore. I had had my suspicions that something wasn’t right but now they had been confirmed. I suspected that Elaine and Lorraine were having a lesbian affair or something and that I was getting in the way. But this was completely unexpected. I was numb, my stomach was churning. I had been dating a guy, kissing a guy and a guy had been kissing me. This was weird, I knew I wasn’t a homosexual, that was what attracted me to Elaine in the first place. She wasn’t a drag queen or some obvious transvestite, she had the appearance of a woman. A very feminine woman.

I knew I was naïve but this, I hadn’t expected this. Who would, it’s not every day that you meet a transsexual? I continued to walk despite the slight drizzle that had started. I tossed the questions up in the air and tried to catch the answers but I was having problems because I didn’t have enough hands and those I did have weren’t budging from my warm pockets.

I thought hard about my future and how it would be with her and without her. She was great fun to be with, she was wealthy, I wasn’t, she was beautiful and I loved the way she looked. She was extremely convincing and she definitely liked me. Or at least she did until I left.

Perhaps I could start another relationship in time and forget all about her? Get married to a nice girl, get a mortgage on a 3 bedroom semi detached house, have 3 kids and work from 9 to 5 every day and go home again. Have a fortnight every year in Marbella or Majorca and go round to her mother’s for Christmas Dinner.

Is that what I wanted? The alternative would be Elaine, who lived impulsively, who lived in the fast lane, who knew what a man like me loved and what she loved in a man.

Could she really be that bad for me to react the way I did? Did she deserve it? Well she had deceived me but then again she had told me. She hadn’t taken the relationship much further than a few days. Her sister had been the reason that happened though. If Lorraine hadn’t forced her, we would probably still be together.

OK maybe that meant she was frightened to lose me. Tell me and I go out and walk in the rain for a little bit or not come back. That was not something she wanted. She wanted me, she really did.

The trouble was I knew in my heart I wanted her and I turned and walked back through the now heavy rain back to the gate. I stood at the gate looking at the lights in the house, standing like some frighten rabbit caught in the glare of a car headlamp. The rain was getting heavier and after 10 minutes I was soaked through. I had to make up my mind, I could either walk past or go back in. I know what she and I really wanted but I was still feeling nervous when stood dripping water on the doorstep and rang the doorbell.

Lorraine answered the door, “She is in the living room, just go on through.”

“Thanks Lorraine,” I said and walked through to the living room where she was perched on the massive settee.

She turned as I entered and smiled. I just stood there dripping water all over the clean carpet and she came running. “You came back, you came back,” she said squealing with delight.

“Yes I came back, please give me a little time, but yes I would like to remain your boyfriend, if you will have me."

The kiss told me the answer and I melted, I knew I was hooked. As I held her I looked over at Lorraine and watched her leave the room with tears in her eyes.

- Chapter Four – Our Relationship Starts -

I telephoned my folks to say that I would be staying at Elaine's house for the rest of the weekend. She put on a flowing kaftan robe and we went back to the settee where we cuddled and kissed

"I feel so happy that you haven't left me to go home," she said in between a heavy bout of kissing. “Where did you go, what did you do?”

“Oh I just wandered about in the rain, thinking things through in my mind. I never imagined this would happen, I thought of the alternatives and what you meant to me,” I answered honestly.

“Well what do I mean to you?” she asked.

“This,” and I reached forward and gently kissed her on the lips. "Heh, I've just realised that I just kissed a guy and it didn't feel too bad," I joked.

"I'm not a guy anymore," she looked at me with her lip turned down.

"Just kidding, no guy could ever look like you and from what I've seen you are more woman than I could possibly imagine. Since I met you have been in my thoughts constantly and I hope that I can be part of your life for a long time to come."

With that she pulled me down onto her lips again and I parted them with my tongue. She allowed me to enter her mouth and soon she was darting her tongue into my mouth as our saliva mixed together.

When I pulled back I said, "have you done anything to your lips? They seem so much more fuller and kissable."

"It took you a while to notice but yes the doctors gave me collagen injections to make the lips thicker and to have more pout."

"I think they succeeded." I added looking into her doe-like eyes. I think I was falling in love.

"John, I want to show you my commitment for you. I have never done this with a man before but I really want to give you an orgasm in the only way I know how."

"What do you want to do?" I asked.

"Will you go upstairs and take a shower and then go to the middle bedroom and I'll soon show you what I want you to do."

I was soon scrubbed clean and was towelling myself dry, when Lorraine walked in the unlocked bathroom.

"I'm sorry," she said as I quickly pulled the towel across my middle. "I didn't realise you were in here but I really needed to use the toilet."

"I'll get out of the way," and left her while I headed to Elaine's room.

Entering she was in a pretty lace night-dress and I came right over to her and kissed her on the mouth before moving to both breasts.

"Oh John that was so wonderful. Now it is my turn to show affection towards you. I want you to lie down on the bed with your arms outstretched."


"Just do it and shut your eyes."

"OK." And seconds later my wrists were secured to the bedposts by two hidden handcuffs.


"I don't want any interruptions," she said, "and the handcuffs ensure that. I hope you don't mind some mild bondage but I want to gag you with this now.

She was holding up something that looked like it came off a pool table with a leather strap and buckles.

"What the hell is that?" I shouted.

"It's called a ball gag and I want you to wear it as you go into orgasm," and with that she inserted it into my mouth stretching my lips uncomfortably. My teeth stopped my tongue pushing it out however as she moved her breasts in front of my face she reached and tightened the buckle of the strap behind my head.

"The last part is this face piece that straps across the front and it gives you a really helpless look. I hope you enjoy this," she said as she buckled the four straps.

I just shook my head but couldn’t talk. She treated me to the sight of her gorgeous body. She floated about in a pair of wicked looking black patent 4” stilleto heels.

She put her leg across my body and knelt such that her hehind was on my stomach. She bent forward and kissed my forehead, then she said, “relax this is my gift to you for coming back to me. I want to please you now like you have never ever been before.”

With my lips covered she smothered the rest of my face with kisses, she nibbled and bit at my ear lobes, I just lay there, my eyes changing from wide open to closed as she touched each new erogenous zone on my body. I could feel her take my ear ring into her mouth and move it with tongue. She sucked it hard and then stuck her tongue into my ear.

Soon she was licking and teasing my chest and nipples with her tongue. She spent a few minutes on both nipples teasing them and biting them gently. Alternating between them, I looked down and could see her blonde mane moving across. I could feel the roughness of her tongue.

Still she wasn’t finished, slowly she licked down my long hairless torso and it seemed obvious where she was headed. She reached my navel and her tonque probed inside it, the feeling was electric as she guided herself down still further.

She licked and kissed the inside of each leg, and cradled my balls with her hand. Her long nails were still squeezing and playing with my nipples. She would pinch them and pull them out gently. Her nails looked like clippers with my soft flesh caught in between. I was so turned by this witch and I couldn’t lift a finger to help but then that had been her plan.

My penis was fully erect and she scraped at it with her nails as she finally guided it into her wet mouth. I looked down between my legs and saw her take all 7 inches with great relish into her mouth. She started bobbing up and down and when she could feel that I was coming she would stop and concentrate on my breasts again. This went on several time, each time I was becoming more desperate, I cried through the gag asking for release from both the bonds and my erection.

Finally this six or seventh time, she kept me in her mouth and seconds later I was spent. She swallowed every drop of my sperm production of the last few days and it was without doubt the best orgasm of my entire life.

As my erection subsided, she lay alongside me still tweaking my nipples and I tried to remind her of my still helpless state.

“Oh OK, I’ll let you loose now, if that’s what you want,” she said

She quickly released me and then snuggled her head up into my armpit. I stroked her hair and I finally I got my breath back enough to speak. "That was incredible you know exactly how to please a man."

"May be it’s because I was a man in a past life," she smiled. "I just want to make you happy and I hope that our relationship can grow. I have never ever done that before and I just wanted to show how much I cared about you."

"Elaine, I have been thinking that for this relationship to work, no one must realise that you are a transsexual. I'll have to expect you to be as feminine as possible in your mannerisms at all times. You may not like it but that must mean you wearing a dress or skirts only. Please do not cut your hair and despite your work, I like your long nails so please do not shorten them. You walk so well in heels and I want to see you wear them all the time even in the house here."

"If it pleases you master," she interrupted.

"It's not that, you are my icon of femininity and I do not want you to change, so promise you'll do all that for me."

"I promise because it's an easy promise to keep. I like wearing that stuff anyway though it will be interesting so see me riding a horse in a skirt tomorrow," she said.

"What will happen between you and Lorraine now I'm here," I asked ignoring her last comment.

"We should continue to be good friends and act like sisters rather than as husband and wife, our divorce came through two weeks ago, so technically I am a single woman now but my birth certificate cannot be changed."

"I don't even know what age you are. What age are you Elaine?" I asked

"How about 25 days old!" she replied laughing.

"No how old are you really?" I replied.

"I was 19 three months ago why?"

"It is just that you look so much older, so much more mature. You look and act so much like a lady. If you are only 19, when did you and Lorraine get spliced?" I asked finally.

"I had just turned 17 (see note) when we were married and it was good to begin with but then she caught me out and those events have led me to live as a woman for the last 2 years or so."

"You do it so well, like you have been a woman all your life."

"That's thanks to Lorraine who helped me make the transition. She gave me lessons in all manner of things including how to wash dishes correctly and all the other domestic and unglamorous chores a girl must do."

"Like ironing and hoovering," I said smiling.

"Like those, Lorraine was pleased when I took up all the chores that I took for granted as being her responsibility."

I lay on my side with Elaine pushing her buttocks back into my front. She snuggled down under the quilt and fell asleep with her head on my arm. Soon we were both fast asleep.

- Chapter Five – Sunday with Elaine -

I woke up to find Elaine still asleep and attached to me like a limpet. I looked at her face in close and could see nothing in it to indicate any trace of a male past. Her pierced ears and the three hoops in each side, her eyebrows plucked into a fine arch. Her nose seemed pert with small nostrils through which I could see her quietly breathing. Looking at her luscious lips I leaned over and kissed her.

She woke up and stretched hard. "What time is it?"

"8:30am," I replied briefly

"What! I have to be at the stables at 9:30 to exercise my horse."

"Won't that be painful after your surgery?" I asked after swinging my legs out of bed.

"Yes it will be a little sore, but I'll take some painkillers and I can't wait to get back in the saddle. Race you to the toilet," and with that she was gone to take the first call of nature. I strolled after her to find her rising after urinating. She wiped her front and put the tissue in the bowl.

"I like sitting down now, it means not missing the pan like I used to. I'm still finding out how to control my urination muscles now that I no longer have a penis. It's a weird feeling."

With the bowl free, I urinated into it and flushed our combined waste products into the sewer system. I could see that she must have still been having problems because there were small pieces of dried blood in the bowl. The tissue was also discoloured.

"When do you have your next check-up," I asked concerned at what I had just seen.

"On Wednesday, why?" She replied as she stood in front of me with her hands on hips.

"Oh just after seeing what I've flushed down the toilet that's all."

"The blood clots?" she asked. "That's nothing to what I had just after the operation. I could hardly walk it was so painful. Little by little it's been getting better. Sometimes I think that the pain was too much and that I shouldn't have gone through with it but Lorraine has told me that I have changed quite a lot in the last few weeks. Maybe it's the lack of male hormones or something but I'm more at ease with myself. Like this is the way it should be."

We showered together and paid special attention to her nipples and vulva despite being still off limits but she soaped me up and played with my tool until I was spotlessly clean. Soon we were back in the bedroom and she started putting on her riding clothes. When I asked her to wear feminine clothes I hadn't imagined this.

Soon she was standing before me with a tight pair of riding breeches that showed the lines of her panties underneath, she wore a pair of knee high black riding boots while she wore a blouse and white cravat necktie covered by a black riding jacket. In her hand she had her whip, gloves and a black velvet-riding hat.

"Well do you think this feminine enough?" she asked.

"I think you look tremendous, I'm just jealous of the horse who has to support such a gorgeous rear." As she turned to look as I added. "Your bum looks like it was designed to sit in a saddle, your hips are wide and your crotch looks flat and feminine."

She sat down on the dressing table stool and quickly tied her hair into a ponytail before putting it into a hair net. She added some mascara and some lipstick and I watched as she added some blush to her cheeks. I stood at the door and offered to carry her helmet, gloves and whip downstairs as she went through to say goodbye to Lorraine.

We grabbed a quick coffee and buttered bread roll before driving out to the stables. Her horse was in his own box in a farm devoted to equestrian use. She quickly led him out and tacked him up after giving him a thorough inspection.

"I haven't seen him for nearly a week and he is being well looked after here," she said as I gave her a lift up into the saddle. She settled into the saddle and tossed the car keys to me. "I'll be going quite far so if you would like to make yourself comfortable in the car, I'll be back in about half an hour."

"OK, Enjoy yourself," I said as she gathered up the reins and headed out to the bridal path adjoining the stables.

She waved goodbye as I settled back to wait in the comfortable car to wait for her return. After a while watching the other girls and women tacking up and leaving with their mounts, it struck me that this activity at least in Britain seemed an almost exclusively female pre-occupation and Elaine seemed so perfect in this role.

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