A Friend in Need is a Fuck Indeed Ch. 06

''What about you?'' I interrupted. ''Amelia's gone, at least from me. How do you feel about me being here?''

''I love Amelia. I owe everything to her.''

I felt like saying ''Do you?'' but I let it go. Instead I said, ''I don't want this to be blackmail simply because Amelia told you to meet me.''

Chloe looked puzzled for a moment and her head tilted slightly to one side while she processed what I'd said, then she responded.

''It's not blackmail, Amelia asked me to help out a dear friend of hers and that's what I'm doing.''

''If I can be frank.'' I was conscious that I was sounding rather pompous. ''Have you known many men?''

Chloe paused and I am sure under her fringe, her forehead was crinkling.

''Not in the Biblical 'known' no.'' I thought she would smile after saying that, but she remained serious. There was a pause before she continued.

''I understand about men and ....'' Chloe stopped for a moment and drew in a breath before continuing. ''And Amelia said that I was ready for a man, and that you should be that man. And that you were the right man for me to continue my journey.''

I didn't say anything although I think Chloe expected me to. I hated anything about life being a journey and maybe it showed on my face. Chloe was staring at me; in fact, we were both staring at each other as though waiting to see who would be the first one to blink. She was absolutely beautiful. Definitely a clone of Jane Birkin, sitting there as though she was expecting Serge Gainsbourg to join her on the sofa. Instead, she got me.

Her mouth dropped open as I moved over and took her in my arms, her long brown hair falling everywhere. I kissed her gently on the lips and then again with a longer kiss. Slowly I undid the cord of her dressing gown revealing two large breasts each with a hard upstanding nipple. I reached for the nearest breast and felt it with my hand. It was much larger than Amelia's and it was firm and full. I lowered my mouth to the nipple and gently sucked it. I felt Chloe tense but was it with passion or the novelty of a man, I couldn't be sure?

As Amelia's lover Chloe would have done everything a woman can do with a woman, and everything that Amelia could do with a strap-on or dildo would have been done. I removed my hand from her breast and carefully placed it on her thigh. Chloe didn't open her legs, so I gently moved my hand between them. She was unshaven and looking down I could see a tuft of dark brown hair.

Chloe started to tremble as I parted her legs and placed a finger between the lips of her pussy. She was damp rather than wet but as I titillated her clit her juices began to flow. I felt her trembling as I teased the entrance to her vagina with my fingertip. Then she let out a long ''ooooooh'' as I slipped a finger in and up. My goodness Chloe was tight. I was surprised because Amelia had told me that she regularly dildoed Chloe, but maybe her nerves had caused her pussy muscles to contract. I pushed another finger up, which brought another gasp.

Then I slowly eased my fingers in and out and Chloe went limp against my other arm. She began to tremble and murmur but I didn't want her to cum yet. I withdrew my hand, stood up and unzipped my fly. I released my cock and it stood out hard and erect, seemingly proud of its length and thickness. Chloe opened her eyes and they widened, obviously shocked at the cock inches from her face. I paused for a few seconds then told her rather firmly.

''Suck it.''

She took the head of my cock into her mouth and moved her tongue around the glans. Amelia must have worked hard at training her because Chloe didn't just stick it in her mouth and wank the shaft. Instead, she continued to use her tongue to tease the glans, then began to bob her head up and down taking more and more of the shaft into her mouth.

The movement of her lips began to do their work. I could feel the sperm beginning to churn in my balls, eager to begin its journey up my cock. But I didn't want to cum in Chloe's mouth. I gently stroked her face, she looked up -- a picture of innocent beauty spoiled by the obscene bulk of my cock filling her mouth. Instinctively she opened her mouth and I withdrew my cock.

Still standing I pulled her dressing gown off, she was now completely naked. My God she was gorgeous, long legs, taunt stomach and large but not disproportionate breasts. All set off by that beautiful face. Amelia had always looked innocent but was totally debauched; Chloe looked innocent and although she had just been sucking my cock, she still looked innocent.

I pushed her back on the sofa, spread her legs and aimed my cock at her pussy. With one hand I guided it towards the slippery entrance of Chloe's hole. Even though it was wet I struggled to get the head in. I have a big cock and it needs easing in gradually. Even with a cunt as big as Sophie's I still needed to steady it on the way up and with Chloe's tight little pussy I really struggled.

Eventually I got the head in, usually that meant the rest of my cock would glide behind it, but this time it wasn't the case. It seemed stuck. I was aware that Chloe was panting and I could feel tremors vibrating through her stomach, but I didn't know whether this was with pleasure or pain. I pushed again and Chloe arched her back and let out a loud ''Oh!!!'' This alarmed me and I withdrew my cock which began to soften and shrink on exposure.

''Are you all right?'' It was a stupid question, but it came out automatically.

''It's so big.'' Chloe kept her eyes closed as she spoke, but she kept her legs open. The lips were still parted from the efforts of my cock and some juice had begun to ooze from her pussy.

''Do you want me to stop?''

''No, try again.''

I tried again, and another time but I couldn't seem to get more than glans deep. I was thinking of calling it a day when Chloe suggested changing positions. She would go on top. This she did. I supported my cock with both hands while Chloe positioned herself above, then she reached around with one hand to guide it in. Gradually she lowered herself down. It was tight, but the glans went in and gradually the weight of Amelia's body began to ease her pussy further down the shaft. With a couple of stops and much panting Amelia managed to fully impale herself on my rock-hard cock. It was completely in.

It was a very tight but exquisite fit. I could feel Chloe's cunt muscles gripping my shaft and the knob head was being sucked into the soft, hot petals filling the depths of Chloe's vagina. She moved slightly to adjust her position, and as she did so her cunt muscles grabbed my cock in a vice like grip. Then they relaxed, but as she moved again, my cock was once more firmly grasped. It was a torture of sensuality, my cock tingled from glans to root.

My sperm demanded release even though I hadn't even begun to thrust. I had anticipated this would be the start of a long fucking session; but as I looked up and saw Chloe's beautiful full breasts swinging with her body's movement, I couldn't control myself and I shot a huge jet of sperm deep within her. She let out a shriek as I pushed up still further shooting out more cum. Then I shot another jet, and as Chloe fell forward gasping for air, her cunt muscles clipped me again and I continued spurting. As she leant back to gain her balance it happened again. Her cunt muscles were milking me dry, soon my balls had been completely emptied.

It was my turn to pant. I backed away and my cock slid drained from Chloe's pussy, as I withdrew a surge of cum oozed from her vagina. Chloe slumped back against the sofa.

''Are you all right Michael? Was it good?''

I was still panting and hadn't recovered from my sensual mugging. I didn't reply but slipped to the floor in front of Chloe, parted her legs and started licking her pussy. I had to wipe some of the cum from her vulva to make enough contact, then I began my well-practiced technique.

Having spent so much time bringing both the demanding Amelia and Sophie to climax I knew the best way to satisfy Chloe with my tongue. I started by licking around the sides of her clit, first one side then the other. Up and down, up and down. Soon I could feel tremors spreading through Chloe's stomach and as my tongue lapped back and forth, she raised her lower body to best accommodate it.

I kept her on the edge for as long as I thought she could stand it. Then the trembling and shivering of her stomach told me to concentrate on her clit. As I did so Chloe's whole body began to shake. I reached under her and inserted the tip of my finger into her arse hole. At some stage she would be having my cock up there, but for now I would simply tease the nerve endings around her rectum.

When Chloe came, I had to grip her tightly around her buttocks or her spasms would have shaken me off like a wild unbroken horse throwing a rider. I held on and continued licking even as a mixture of cum and Chloe's cunt juices flooded over my face. She certainly came with a vengeance, her orgasms came one after another in quick succession, each one accompanied by a moan which grew louder and louder until it was one long spluttering call of ecstasy. At her final orgasm she threw her head right back almost hitting the wall and shouted out ''CUNT! CUNT! CUNT!'' Then she fell forward, tumbling us both onto to the floor.

I helped her up and laid her on the sofa, draping her dressing gown over her naked body. She opened her eyes, stared blankly then looked at me and said, ''Michael, Amelia said you knew how to satisfy a woman, and she was right. You are a darling.'' Then she paused, and slightly tilted her head to one side.

''Amelia told me I would become fond of you, and I think I will be.''

Normally I would have fucked Chloe again, or at least tried to, but I had found the evening's experience so odd that I just wanted to go. I needed to reflect and draw a breath, to try and get an overview of what was going on, and my part in it. Chloe was now part of the drama and I was uncertain about her role in the future, and for that matter I was uncertain about my own role in the future.

I made an excuse about having to get up for an early lecture the next day and left. Chloe dozed off while I was dressing and I let myself out without disturbing her.

* * *

The next day I was back at Sophie's. She had texted me in the morning and told me to come around to tell her about my visit to Chloe and to talk me through an arrangement she was making. This was her way of saying she was planning an orgy.

After I arrived, I fucked Sophie in the large bedroom on the first floor. Sophie's mature cunt was much looser than Chloe's and my cock easily slid up her well lubricated hole. I pounded her hard for as long as I could without cumming and then turned her over and fucked her in the arse. Sophie was passive throughout; as she often said, ''Sometimes I just need to lay back and be fucked.'' And that was how it was that morning.

Afterwards we dressed and took tea in the sitting room. The moment I sat down Sophie began to quiz me about Chloe. I told her everything that happened, particularly how tight Chloe had been. Sophie listened intently and didn't interrupt. When I had finished, she simply said, ''I think it will be all right in the long term. The difficulty will be integrating her into our arrangements, but we will take it slowly. That's the best way. In the interim it will be up to you to expand her horizons.''

Then Sophie began to explain our next project.

'Remember Max?''

''Yes, I do. He fucked me so hard I thought I was going to split in half.''

''Well, he wants to see you again.''

''What, dressed up?''

''Yes.''

''I won't do it.''

''Michael you were beautiful. I loved you as Jane. We all did.''

Strangely enough at the mention of me being Jane, a tingle went through my cock.

Sophie continued, ''You know you will enjoy yourself, and there are other rewards.''

This was news to me.

''What other rewards?''

''Max is a very wealthy man, and he is willing to pay a thousand pounds to you to cover your expenses, as well as a further donation to Piers' projects. That's a lot of money.''

She was right there, that money would make me a wealthy student.

Sophie caught my eye and smiled.

''You see, you are interested.''

I couldn't disagree, so I didn't.

''Although the meeting won't take place here, it will be at The Royal.'' Sophie paused, then said, ''You will meet them in the bar there, have drinks and then go upstairs to their suite.''

'' 'Them'? Max is not alone.''

''No, his wife will be joining in. That's what makes it even more exciting for him, as she's never done a threesome, let alone with a transvestite.''

It felt strange to hear myself described as a transvestite, but it was accurate enough.

''So how come she's agreed to a threesome?''

''Who knows? They are a mature couple, maybe she wants some excitement, maybe she just wants to please him. Anyway, you will do it won't you.''

''Yes.''

''All right, this is how I see things working out.''

When it came to matters of sex Sophie was the ultimate planner, as I knew so well.

This orgy was going to be more elaborate than anything I had done before. Usually, Sophie acted as the ringmaster of our sexual activities, preparing the setting and often directing the proceedings. This time I would be on my own, that is apart from Max and his wife. It was mainly acting out Max's fantasy. I would meet them in the bar of their hotel, have a few drinks and then go up to their room where I would have sex with both of them. The way Sophie explained it, it was all very straightforward; but I would be going as Jane.

Being Jane had been fine at the Prof's house where Sophie prepared me for my transition and I entered one room a male and went into another as a female. This time I would have to go to Max's hotel and meet them in a public place. I had to be convincing and as Sophie explained how we were going to do this I trembled with excitement.

* * *

A week later I was in the back of a cab being driven to one of the city's top hotels. My whole body felt electric, sexuality was oozing from my pores. I felt my cock trying to break out of the confines of my tight black panties. I kept crossing and uncrossing my nylon clad legs, I flicked my long black hair first to one side and then another. I played with the hem of my black Chanel style dress. I was Jane all right and I was ready for anything.

The cab stopped outside the entrance to the hotel, I paid the taxi driver and tottered inside on my shiny high heels. There were a few drinkers at the bar, one young man caught my gaze and ran his eyes approvingly up and down my body. I found an empty table and sat down. I was a little early, it was ten to eight and we were due to meet at eight.

Sophie had done a good job. As usual she had prepared me with a luxurious scented bath. Then having paid a lot of attention to washing my cock and arse, an excuse to tease both, she dressed me in new exotic underwear. With each new item of clothing, I felt more sexual and more exotic; black lace panties, suspender belt, black nylons and matching padded bra all embraced my body. My long black wig and hoop earrings provided the perfect framework for my heavily made-up face. Sophie was an artist with makeup and she applied her talents with real skill. Looking in the mirror I have to say that bizarrely I actually fancied myself. And here I was sat at a table in the bar of a five-star hotel waiting to have sex with a couple old enough to be my parents.

Suddenly there was a gentle tap on my shoulder and I turned my head to see Max looking down on me. I remembered him well; tall, with fairly long grey hair brushed back from a rugged but handsome face. For someone nearly sixty he looked good. I also remembered that big cock which had almost broken me in two when he had first fucked me all those weeks ago. He was wild that night, almost out of control with sexual passion.

''Good evening, Jane. So good to see you again.''

''And good to see you.'' I replied, keeping my voice as soft and as gentle as I could as he kissed me on both cheeks. Sophie had spent hours helping me develop a feminine voice and feminine manners. She was pretty confident I was safe on the streets as a girl; although she said I seemed to give off a slightly slutty aura, but she didn't want to change that as it added something to my character.

Max introduced me to his wife Elizabeth, who smiled at me but couldn't conceal her nervousness. We didn't kiss.

''Jane you're beautiful.''

I thanked her for the compliment and had a good look at the wife of this rich bisexual man. Elizabeth was probably in her early fifties, shortish dyed blond hair, and a face mature but still attractive. She was rather plump with big breasts straining to burst out of a well stretched but obviously expensive dress. She had sex appeal, but would she take my cock up her arse?

They sat down and ordered drinks and I had another prosecco. We made small talk about the weather and how spring couldn't be far away. Just as I was wondering why we had met down here to trade verbal nonentities when we could be having sex in Max's hotel suite, I felt his hand graze my thigh. He had leaned in close to the table and with his back to the bar, so that no one could see, he rested his hand on my knee. It must have been obvious to Elizabeth, but she didn't seem to notice.

A moment later his hand had moved higher so that it crossed my suspender belt and reached the edge of my panties. Max's hand was trembling as his fingertips slipped under my panties and lightly touched my cock. Although the light was dim, I could see that Elizabeth was blushing and she looked from side to side to see if anyone had noticed, but nobody had.

This must have given Max one of the thrills he was after as he continued this game for quite a while, occasionally withdrawing his hand when a waiter came close, or someone walked by to another table. Then he grabbed my hand and gently dropped it on his crotch. Yes, he was excited. In anticipation he had surreptitiously unzipped his fly and I could feel the hardness of his confined monster cock. It seemed as though he had a series of coke cans in his underwear, it was that big and hard. I stroked it with one finger. Max looked down with obvious excitement as I teased him with my finger up and down his clothed cock.

Then it was up to the suite on the top floor. As soon as the lift doors had closed, Max grabbed me and pushed me against the back of the lift. He pressed his lips on mine and I felt his tongue darting in and out of my mouth. Elizabeth watched intensely, and in her well-lit reflection in the mirror I could see her face was bright red. On impulse I pushed Max off, turned to Elizabeth and kissed her full on the lips. I didn't close my eyes and nor did she, hers were wide open with surprise and wonder and her lips were hot and damp.

Then the bell dinged, we were on the top floor. A few minutes later we were in Max's suite. The door had barely closed when Max took control.

''Jane, strip Elizabeth.''

Even I, with the experience of numerous bizarre orgies at the Prof's was a little taken aback by this command, but I did what he said. Throughout this, Elizabeth stood still like a tailor's dummy as I removed each item of clothing. I left her bra and panties on to the end. Unclipping Elizabeth's bra released two huge droopy breasts which descended onto her rather large, rounded stomach. I had some trouble removing her panties as they were very tight; but in the end they were down and off, revealing quite a small neatly shaven pussy. I say small as the lips didn't extend out from her vagina. It was just one long slit.

I looked over to Max awaiting further instruction and my mouth fell open at the sight of his enormous cock. He had removed all his clothes and his thick cock stuck out horizontal from his body. It must have been ten inches long. It was rock hard though even in its horizontal state.