Teddy's Story

"Sit on that chair, Teddy."

When I did, with my back to the mirror, she again stood right in front of me.

"Would you like to see me again, Teddy, like yesterday?"

I swallowed hard and managed to gasp "Yes please."

She started to unfasten the buttons on her dress right at the top. When she got down to her middle she said, "You undo the rest for me."

I couldn't believe it. I was going to undo a woman's dress and see inside.

My fingers were really trembling as I reached out and fumbled with the buttons.

She just stood and waited and let me struggle and one by one I got them all undone right down to the bottom of her dress.

I didn't know what to do, or could do, or if she would let me do anything else and I looked up at her face.

"Open it."

I pulled it open and again saw her breasts all held up in her bra. I looked down over her tummy and instead of baggy, blue, girl knickers with elastic round the leg she had panties. A sort of pink, silky stuff and lace round the legs and the legs were all baggy.

She turned her back and said, "Unfasten my bra."

I stood up and there were clips holding it together and I undid them and she shrugged and the straps slipped off her shoulders and the bra fell down on the floor. She turned to me and I saw her bare breasts with the nipples all pink and hard sticking out at me.

"Stand behind me."

She got close to the dressing table and I could see her in the mirror from her face to her thighs as I looked over her shoulder. Her naked breasts and her woman parts covered in this pretty silk.

"Put your arms round me and feel my breasts."

I saw my hands and arms in the mirror and my hands reaching up. This had to be a dream. It couldn't be true. But it was true because her hard nipples were under my hands and she was whispering "Stroke them gently."

My hands were shaking like mad and my dick was hard and trapped in my underpants. I was holding her close to feel her and my trousers were hard against her panties.

Then she said "Take all your clothes off."

I couldn't get them off fast enough and while I did that she just stood waiting in front of the mirror. Then I stood close and felt round for her breasts and my knob touched the silk panties covering her bottom cheeks and it felt really good and I knew why Uncle Reg liked feeling his knob on me just there. I pushed my dick at her and she pushed back at me. We kept doing that. Both of us pushing at each other and my dick started to push the silk between the cleft of her cheeks.

"Feel my breast with one hand and feel underneath my panties with the other one, Teddy."

I watched as this hand, my hand, slipped down over her hip and like Uncle Reg had to me, I put my hand under the leg of her panties and felt up at her. My fingers were in her hairs and I was desperate and grabbing to feel more.

"Gently, gently, Teddy. Be gentle for me."

I tried to be gentle but my hands were shaking and I had my fingers in between her legs and it was wet and slippery and there wasn't a dick hanging there and I exploded my cum between her cheeks and over her panties. My hips were jerking at her as I fucked at her cleft and she was pushing back at me every time I went forward. My arms were holding her tight or I think I would have collapsed on the floor.

I was panting and I could hear her breath, heavy and her chest heaving in my arms. She had one of her hands over mine inside her panties and she was using my fingers to rub and stroke and feel at a hard thing there. Then she was crying out and her hips were jerking at my hand and she was holding my fingers tight between her legs.

After a minute she turned to me and held me tight.

"Teddy that was Mmmmmmmmm. Let me take these wet panties off."

I stepped back and she took them down slowly over her hips, and I saw her hairs and her gap and her legs, then she stepped out of them and we were naked in front of each other.

She took my hand and led me to her bed. I expected her to tell me to lie down for her like I had to for Uncle Reg. Instead she lay down on her back.

"Kneel beside me."

When I did that she said "I'm the first lady you've seen. So you can look at me anywhere and touch anywhere so you can see how a lady is made and where she's different from you men."

WOW she had said "YOU MEN" and she meant ME.

I touched her breast and I saw her nipple go from soft to hard. I stroked it and she told me to kiss it. I sucked on the nipple and I heard her sigh. Her hand was stroking her other nipple.

After a while she said, "Now the other place."

I looked at her and she smiled and her eyes were all soft and a bit puffy and she said, "Yes, between my legs."

She took my hand and placed my fingers in her hairs, then I felt her legs spread wide and she was sliding my fingers in between where it was all wet. She took my middle finger and moved it and there was a tight hole and she pushed my finger tip at it and said "Put your finger in me."

I pushed and I felt the wet warmth of a woman gripping my finger.

"Keep pushing it in and out and don't stop ‘till I tell you."

My finger went right in all the way and when it came out of the hole it was wet. The more I did it the wetter she got and then she put her own fingers in her hairs and started stroking. Her other hand reached down and was feeling my cock, stroking and feeling it. Her fingers were really soft and gentle and not like mine when I jerked it off or Uncle Reg when he made me cum.

Her hand stopped feeling in her hairs and she took my finger out.

"Get between my legs. Hurry. Hurry Teddy."

I knelt between her spread legs and I could see she was all puffy and a bit open from my finger. She took my cock and pulled it to her and I felt the very tip of my knob as she moved it up and down her slit and I got all slippery from her.

She held it still and said "Push. Keep pushing. Don't stop pushing."

It was incredible. My cock went straight in. I felt this wet, warm tightness all around my dick. Her hips pushed at me and I pushed back.

"Keep pushing in and out. Please don't stop Teddy."

Her hips were lifting and pushing and I couldn't get my push at her right and my dick came out.

"PUT IT BACK!" she shouted and grabbed it and held it so my cock would go in her hole again.

Her hands were on my hips now and as she pushed at my dick she pulled me to her and got the timing right so I stayed inside her hole. One of her hands went between us just above my cock and I could feel them twiddling at herself as I went in and out and then her head was rolling from side to and she said "I'm cumming, fuck me, fuck me, fuck me" and her lips lifted right up and held me in the air and she was calling out and making noises and "Yes, yes, yes." Then she fell back on the bed and she held my hips tight to her.

I was hard and I wanted to keep pushing but she held me still for a minute.

Then she said, "Oh, Teddy. You poor man you. I was greedy. Please keep doing it to me."

I started pushing in and out and nearly straight away I felt my legs tingling and it was in my balls, all swelling up and I spurted and spurted like I would never stop. She held me close when I collapsed on top of her. I was sobbing and panting and shaking and she was making little soothing noises to me "Good boy. Good man. You are so GOOD, Teddy. You made me feel like a woman. You were a man for me."

I felt proud and contented and couldn't believe I had done it to her.

My prick slipped out and she pushed me onto my back. She climbed over me and spread her legs over my tummy and I saw her hairs all covered in sticky stuff.

"Watch," she said.

I saw white, creamy stuff drop out from between her legs and fall on my tummy.

"That's your man cum.. You filled me with man cum, Teddy."

For the rest of that week Uncle Reg would do me in the nighttime in his bed.

During the daytime, I would do Aunt Lizzie in her bed.

She let me look everywhere between her legs and held herself open so that I could see where my prick went when I fucked her. She told me how a man had to be careful not to make the girl pregnant and that the man must always be gentle with a girl and never ever force her to do anything she didn't want to do. She showed me how to make the little lump come up for her at the top of her slit and told me it was her clitoris, her clit, and that if the man did it right it was heaven for the girl to let him touch it for her. She told me about contraception, and that she had used a special cream inside herself so that I didn't make her pregnant.

I felt 10 feet tall. She had to use something so my cum didn't make her have a baby. I was a MAN.

Epilogue

She let me go to see her sometimes during the day when Uncle Reg was at work. Not every time, but sometimes, she would kiss me and take me to her bed. She always told me that I would be wonderful for a girl to love. She gave me confidence in being a man.

At the weekend I was often invited to have tea with Uncle Reg and her. Straight after tea she would go to be with Rose and would tell us when she would be back or if she was staying over. Uncle Reg would then tell me to go and get ready and I would use the enema and take a bath. I would get dry and put a towel on his bed and wait for him, naked. Soon he would come to me.

I always liked what Uncle Reg did, being submissive and letting him have me. It was always exciting when he followed me outside at the club, or when he told me to meet him during the dark evenings of autumn when he would take me to a secluded spot on wasteland.

After the war there was no street lighting for years, so everywhere was dark. Quite often we would be aware of dim figures not far away, and would hear female cries of lust as she was fucked by her man and I would picture Maggie's spread legs, her hole leaking cum. Uncle Reg would take down my trousers, cream me and I would thrill to his penetration as the other couple were moaning.

He never asked me to fuck him. I never wanted to. I never have fucked a man. I am content and get the greatest pleasure by submitting.

I always loved what Aunt Lizzie had taught me. Making me a man and teaching me to be patient, to give her pleasure, to help her to her orgasms as well as myself. I discovered the pleasure of being bi-sexual. Without Aunt Lizzie I don't think I would ever have known the intensity of love I could have for a woman.