The Virgin Tranny & the Bride Ch. 08

My transvestite friend Roberta writes to tell me that recent surrender of her boy pussy to her Master was, sadly, not for love but as a means of gaining embarrassing video footage to use as sexual blackmail. Master John is now teasing Roberta and she is about to embark on a new career as a call girl and prostitute.

She writes:

With the lining removed and my dress now see-through I was worried about being sent to the shopping precinct looking like a hooker. However, John had other ideas.

John gave a little laugh and then continued.

"In....fact...," he started, thinking as he talked. "I think it would be good practice for you to have a try now. You look like a hooker and I think you should go and join them for a while, see how many punters are interested in a short time, with a gorgeous young tranny. The girls, Jodie and Julie, keep asking if you really have gone out onto the street as a bride. Well, they are going to see just how willing you are to go anywhere that I suggest, as a schoolgirl, as a bride or, as a very provocative hooker."

He stopped talking as he dialled a number on his mobile phone. Sarah answered.

"Hello Sarah love. I have a new girl coming to join you tonight and I want you to look after her. Her name is Roberta and she will be with you in a few minutes."

He hung up and smiled broadly.

"Off you go sweetheart and earn a few pennies to pay for the sexy dress you have on. I can see your tranny cock twitching with anticipation as I talk and I bet your pussy is positively pulsating with excitement."

"Please John, don't make me do this just yet. I want only to be your shemale lover."

"I'm sorry sweetheart. It's not me, but the girls think we are telling them stories about you as a bride on the street, and it is much too early to be out there in your bridal gown at the moment. However, after you have done this, and much later into the night, you are going to let Jodie and Julie see that you are not scared to go out in the gown that you wore on our wedding night and have my slutty wife fuck you with her big black dildo. I might want some after her, maybe we will all have some, your first gangbang as tranny."

He smiled as he watched me.

"Bring a mirror girls and let our sexy shemale have a look at herself before she goes out on the game."

Jodie brought a full-length mirror.

With my hair and make up redone and looking perfect and my dress showing off my cleavage adequately, but leaving nothing to the imagination, I looked at my cock and my sexy underwear through the layers of the chiffon skirt. I looked at Margaret and received no sympathy. Jodie left the room before me as Julie kissed my cheek and John just smiled and waved goodbye.

Jodie was standing at the front gate as I stepped out onto the street. Darkness was falling but it was much too early to be going out dressed as I was.

"We never said anything to John," Jodie quickly confessed as she handed me a small black handbag to carry in front of me to hide my sex. "He's making that up because Julie and I know you love dressing as a bride. He's trying to drive you against us."

"He is like that with us too, he makes Julie and I do things in public when we go to Russia."

"Russia?" I questioned.

"Oops, sorry I wasn't supposed to say anything. Please promise not to say I told you. I will be in real trouble if John finds out I told you."

Jodie held me close, her right hand on my cock as she looked directly into my eyes for an answer. I nodded and she kissed me, pushing her tongue into my mouth as we squeezed each other tightly.

"I want to be your bridesmaid again tonight if you go onto the street. I want you to lift your bridal gown and fuck me so hard. I want to thank you darling."

We walked down the cul-de-sac together and she was full of encouragement for what I was about to do.

"You look superb darling, gorgeous and so sexy. If I was passing and saw you, I would want to pay to have sex with such a gorgeous shemale."

We kissed and then I passed the barrier, making sure my handbag hid my biggest secret, the coolness of the dusk air teasing the soft layers of my dress against my clit.

A few minutes later I met Sarah at the mesh gate, this gate closes off the lane that runs behind my parents and John and Margaret's house.

"Wow," she exclaimed. "You look fantastic, give me a twirl."

I did so and held my arms aloft and let my dress float as I turned.

"You bloody dare devil, coming out here like that," she gasped on seeing my naked ness beneath my dress.

Just then a truck went passed and gave a blast of the horn as Sarah waved. Her phone began to ring. It was John.

"Are you really certain you want me to do that," she asked before hanging up. I looked anxiously at her.

"He wants me to ring a special client of mine and offer him a very special two for the price of one at my place."

I knew I looked worried.

"Don't worry, my friend will love you, he's bisexual and between us we will give him lots of fun. He does like a girl in petticoats and you can borrow some of mine."

I was shaking, a mixture of the daunting task ahead and the cool breeze. Sarah and I cuddled together much to the amusement of passers by. Then came a voice from behind the gate, it was John. He had walked down the lane at the rear of the house.

"Is it on then?" he asked. Sarah told him it was but her client was calling back to make the arrangements.

"Fantastic. Now let me have a few photos to mark this wonderful occasion."

John pressed his camera lens against the mesh gate as Sarah and I waited for an opportune moment. She opened her coat to show off her tiny white negligee, her breasts uncovered and her pussy equally visible. John wanted more from me and I had to raise the hem of my dress until my drooping tranny cock was in sight. He chortled and left.

A few minutes later and her phone rang.

"We are going to be picked up in five minutes and he wants to take us to the country."

I was very worried. What if he didn't like me? What if he recognised me? Did he really know I was a tranny? All those questions, and others, were still running through my mind when the car drew up. Sarah went into the front seat.

I was introduced to Jeremy and he turned to shake my hand and give me a look.

"I see you girls are not wearing petticoats tonight," he said after giving me a nice warm smile. I felt better.

"We can go and get them if you want Jeremy," Sarah offered.

"No, not tonight. I am actually entertaining but could not refuse the offer you and John made to me. To be the first with such a stunning beauty as Roberta is worth the risk of taking some time out for an hour or so."

Jeremy looked in the rear view mirror as he complimented me. I smiled back at him.

"I hear your speciality is bridal wear?"

"Yes, yes it is," I replied, wondering how he already knew that.

"Well if everything goes well tonight I look forward to you being my pretty little bride in the very near future," he continued as we reached the city limits and the darkness.

As the interior of the car went dark I felt I knew Jeremy's face from somewhere but could not think where.

"How much do you think it would cost me to have you both as my gorgeous sexy brides' after you've done a nice sexy show for me?"

"Don't know, I'd have to ask," replied Sarah before adding. "Would you like Roberta and I to swap places and let her play with your cock as you drive along?"

"I'd really love that," he replied, applying the brakes at the same time.

"My, you are a big girl," he said referring to my dangling cock as my dress rode up.

"Very sexy," he confirmed as he drew my right hand over to open his zip.

Cars flashed past in both directions and offered enough light to let me see what I was doing. I felt excited and strange as I reached in through his open zip and retrieved his semi-swollen cock.

"Just hold me in your hand for a while," he requested as he started to drive again. Then as he changed into top gear he allowed his left hand to drop onto my right thigh.

"Please let me return the favour."

A few inches and the hem of my dress was raised enough to release my dick which Jeremy took hold of.

"You are rather big," he commented again. "I'm pleased I'm having sex with you and not the other way round for tonight at least."

He began to stroke me and I did the same to him as Sarah watched through between the seats.

Then we turned off the main road.

"Just a couple of miles to go my sexy girls. Would you like to suck me a little Roberta?"

He put on the interior light and our pace slowed to a crawl as I adjusted myself and eased my head into his lap. The first thing I noticed was the sweet smell of fresh soap. I felt good and Jeremy gasped loudly as I ran the tip of my tongue around the tip of his cock. Gradually I eased more of his very stiff five inches into my mouth and sucked. He loved it and I was eager to impress. Perhaps I was too eager as he had to ask me to slow up or he was going to explode.

Moments later the car stopped. We were at a house formerly owned by his parent and now only furnished with a large table in the centre of the sitting room.

"Let me have a look at my two gorgeous girlfriends," he suggested on finding a bulb for the light.

I liked this guy, he made me feel really good as a girl.

"Very nice Roberta. Sexy looking girl on the top with gorgeous face and nice tits and a big horny dick below her dress, Wonderful."

He had lifted the hem of my dress with one hand and held my swelling cock in the other.

"You know me Sarah," Jeremy went on. "What do you think I would like best to do with my favourite girl and her transvestite girlfriend?"

"I know what you want Jeremy," replied Sarah immediately as she slipped off her coat and threw it over the top edge of a door. "You want to watch me and Roberta giving you a little sexy show over there on that table, a little oral, a little teasing for your cock, and then watch her force her massive tranny dick into my sopping pussy. You can watch her fuck me for the first time before you force your cock into her tight boy pussy and give us both a good fucking."

She gave him a condom before leading me by the cock to the table. As we got ready she was ever so nice to me.

"You've been wanting to do this to me for a long time, haven't you? All those nights wanking off to me in the lane, wanting to fuck me. All those nights we have been so close as we fuck with John and Margaret and now our time has come to do it."

Sarah sat me on the table and made sure Jeremy had a good view before she began sucking me. I looked down on her head bobbing into my lap and, her naked body, the memory of the first time I realised she was naked on the street except for her coat. Jeremy was close by as he watched our show and I managed to reach out and get my hand onto this cock. Gently I eased him to the side of the table and slipped my mouth around his tasty little shaft.

"Fantastic," he uttered as I cupped his balls in my hands and sucked and sucked until he spurted his pre cum into my mouth. My attention to him took my mind off the equally fantastic time Sarah was giving me. Jeremy spurting into my mouth signalled the time for change and Sarah lay across the table with her wide-open legs held over the edge. I endeared myself further to Jeremy in the process.

"Jeremy, I would really love you to ease my tranny cock into Sarah," I said in my most demure voice. " I have always wanted to fuck her long before I was age to do so and I would just adore having a lovely man like you bring us together for our first fuck."

As I spoke I brushed the chiffon layers of my dress against his dick just to keep him interested and nice and hard.

"You sexy beauty," he cried as he took up my suggestion. Sarah joined in.

"Jeremy, if you want to see her being really sexy you ought to see her as a bride. I saw her last night and Roberta looked absolutely stunning."

I gasped as I slipped in to Sarah with relative ease and still held onto Jeremy's cock. Sarah clasped her legs around me and held me tight.

"How does it feel big boy?" she asked. How does it feel to be fucking me after all this time, am I up to your expectations?"

I thrust into her and began pounding deeper and deeper into her, causing her to draw breath as I did so. I kept the momentum going as I gave her the fucking I had always imagined giving her, her voice trembling as she tried to speak.

"You know you are rather special to me," she paused and then continued, "So special that you are the first to fuck me for months without a condom."

Jeremy left the room. He had returned to the car to put off the lights. In his excitement he had left the headlights ablaze. He also retrieved some gel at the same time which he readily applied to my boy pussy, a finger slipping the cold lubricant into me in readiness. I watched him slip on his condom and use the fabric of my dress to get himself fully hard again before he opened my thighs as I leaned across the table on top of Sarah. She held me tight as I felt the tip of his cock enter me. He was nowhere near as big as John but I still felt pain as he drove deeper into me.

"Relax sweetheart, let Jeremy work himself into you. Just think of being his kinky bride sometime, being my kinky bride too, both of us fucking your sweet little boy pussy." As she spoke the pain subsided a little as Jeremy began to fuck me but I continued to gasp and grunt and make noises with each thrust that he made.

"Let him do the fucking darling. Let him choose the pace and see if he can fuck us both at once."

Jeremy gradually increased the pace and I felt myself thrusting into Sarah who was really loving the kinky scene. I was sweating even though the night air had turned a little cooler but I was really enjoying being fucked more than I had the night before. Jeremy was more loving than John had been and being in Sarah at the same time was so wonderful. We were really having a great fuck and I could feel him getting close to orgasm.

"Please don't cum in me Jeremy," I stuttered, "I want to taste your cum and share it with Sarah."

He seemed to understand my request and soon after in a hail of fuck words and deep breathing he pulled out of me with a plop and removed his condom before climbing onto the edge of the table to kneel before me. Greedily I grabbed his cock first and began sucking him, the salty taste of his seeping cum mixing with the strawberry flavour of the condom he had just removed. Sarah lifted her head and joined me licking at his shaft from below as I did it from above. He was in heaven, loving every second of our attention, crying out he was about to cum.

The first salvo hit me on the chin and ricocheted into the face of Sarah. I caught the second directly in my mouth and then offered his spurting cock to Sarah for a mouthful. Jeremy went delirious with excitement when he saw me lick his cum from Sarah's face and then kiss her full on the lips as we swallowed it between us. He had never ever been with two such kinky people.

He paid us well too, insisting on paying for both of us rather than the original two for one offer he had been given.

"Don't tell John I paid you twice," he said as he dropped us off at the mesh gate. I asked Sarah what he meant and discovered something new about my new sex life. John was now my pimp. He was a pimp for Sarah, for four other girls in another part of the city, for his two video porn stars Jodie and Julie and now me. He would be taking half the cash Sarah and I had earned.

Back at Margaret and John's, Sarah and I showered together and finished our fuck. I was a boy again and we ended up doing it doggy style as Sarah leaned on the edge of the bath "Who's a kinky little girl then," was the way John greeted me as I emerged with Sarah from the shower.

I thought he was referring to my state of undress, dangling dick and swollen false breasts but it was better than that. He took me aside.

"You've been a big hit with your very first client – you have another date with Jeremy next Friday – by yourself."

The stunned look on my face was enough.