Pussyboy

Chapter 1:

This is not so much a story but a confession. The confession is not wholly my idea and not something I wish to share. It contains my most personal thoughts and actions which I am sharing it with you to achieve some sort of redemption.

Before I got married three years ago, I used to see this girl, Caroline. She was attractive in a sexy way but not particularly so. However, she had a great body; lithe and supple with long slender legs, flowing blonde hair. Intense green blue eyes that would stare at me filled with lust while she wrapped herself around me as we luxuriated in each others bodies. She worked at keeping her body in top condition and used all her femininity to entrap her lover.

Our relationship was, for me, one of a convenient alternative to my then fiancée. I did not love Catherine, but she would always be there to meet my desires, to ease the burgeoning libido that my fiancée Karen saw as a chore. For Catherine it was much more. She wanted me, she needed me. She would send me lewd text messages, telling me what she was wearing, where her fingers were, what she wanted there and then and what she would do to me if I was to come around. All this to draw me to her.

It started out as a one night stand, at least that is what I had intended. Nearing the end of a long drinking session on a conference in NY I bumped into her in the lobby of a hotel bar. We chatted and flirted with each other. After a few more drinks she took me up to her room and then used me. Drunken sex is never great but she threw herself into it. After a few seconds of stroking my groin, she quickly got on her knees and pulled my hardening cock from my trousers taking before it deeply into her waiting mouth. She then got me to take her from behind then switching positions more than 10 times before I eventually came with her straddling me, pushing her pelvis down hard onto my member as she held my arms above my head.

It transpired we were both living in London so we exchanged phone numbers as I left her flat. I never expected her to call and I had no intention of calling her.

The day after the conference I got the text message:

My pussy hurts from YOU! But it wants MORE!!

I had already forgotten about Caroline, but her message created a stir in my pants. It was wrong, I was going to get married soon it should never of happened. I ignored her message.

For the rest of the week I received a new message every day. Each one more graphic than the last. She told me she was picturing my cock, she was fingering herself, she was working a banana into her pussy, she was pushing her fingers into her ass. I enjoyed it I have to say. Being teased like this and teasing by not responding. Her messages though were getting to me. I kept thinking about her, what I would do to her and what she would be doing to me. On Thursday night while I made love to my fiancée her image flashed through my brain. The image of her watching me fuck my fiancée from behind while her fingers were a blur between her legs, her eyes burning through mine.......and then I came.

Friday night drinks again, and too many gin and tonics later, another message came through. This time, it just said "I'm waiting" and gave an address. My brain addled, my resolve weakened, I responded. An hour later I was ringing the bell on a door in Notting Hill. A buzzer sounded and the door opened. I made my way up to flat 3.

The flat door was open and walked into a beautifully furnished room Caroline was sitting on the sofa with her legs pulled up to her chest. A skirt and blouse revealing her pale legs and the hint on her breasts pushing against the fabric of the blouse. A large glass of red wine in her hand. She stared at me then smiled:

" I knew you would come" she said.

I sat down opposite her looking into her eyes. Those green blue eyes.

"Yeah, I didn't" and walked over to get a glass of wine. "Haut Brion" you have good taste."

"In all things" she whispered licking her reddened lips.

We then sat there, watching each other, sipping our wine, not talking, soft chillout music playing in the background.

When she finished her wine she placed her glass to the side and reclined along the length of the sofa. Her smooth porcelain legs slightly bent. Her hand began to trace across her chest slightly above and then below her breasts. It was now clear that she was not wearing a bra. My heart was thumping in my chest. I was sitting here, while my fiancee was at home in bed tired out from organising our wedding which was planned to take place in six months time. My excitement barely concealed by the tenting of my trousers as I leaned forward where I sat, mesmerised by her.

Her eyes closed and her tongue slipped between her lips as she cupped her breasts in both hands. A small involuntary sound escaping as her thumb brushed her left nipple, both of which were now prominent against the silk fabric. Long hard bullet like protrusions revealing her excitement.

A hand descended lower beginning its urgent journey. I watched for some minutes as she rubbed the fabric of her skirt, pushing down hard between her legs. I wondered if she had any panties on. I wondered what I was going to do, I wondered if I could handle this. Eventually, my heart racing I crept across the room to place my hand on her ankle. Gently, caressing the pale skin and then working it upwards along her calf and then along the inside of her thigh. Standing staring at her face as my hand reached its goal and felt the wetness of her panties. They were sodden. It was only when my hand touched her there that she opened her eyes and smiled.

My fingers caressed her silken panties, and then worked their way under the moist fabric and then inside her. I stood above her looking into her eyes as one then two then three fingers penetrated her, my eyes never leaving her face. She began panting, pushing back with an urgency against each thrust. The heel of my hand grinding into her pubis, pushing down on her clitoris, squeezing her sex as my fingers sought out her hot inner core.

Then she came. Her hand clutching at mine, sitting up involuntarily as her body was wracked with the force of her orgasm. A couple of minutes later, she turned to me rubbed my tented trousers, and then kissed me, biting my lower lip as she did so.

"You better go" she said.

"What about ME!" I stammered. She told me to take my pants off. When they fell to the floor the exact nature of my aroused state was obvious. My cock was covered in slimy juices, the end purple, completely engorged with my passion. Clearly, it would not take much before I would explode.

Catherine, then took off her wet panties and handed them to me. "Use this" she said. "Do it yourself. Next time you will answer my messages!".

I beg and pleaded but all she would do was watch. Eventually, I relented and wrapped the wet panties around my cock and began stroking up and down my hardened member. I looked into her eyes as my hand pulled down hard, pulling the foreskin right back slowly, and then faster and faster. I had wanted to draw it out, to involve her in some way but after only a few more strokes I was shooting all over the floor my body shaking with each shot. It was fabulous, so strong and hard. I had never really cum like that before. I was shocked.

Catherine then made me clean up my mess. I think she wanted me to lick it up but I just used her panties. She told me to wear the panties home. To remind me of her she said. After some haggling about the risks I would be running I agreed. I have to admit it felt pretty good too. The silk panties and cold wet cum clinging tightly against my ass and balls.

When I got home I had a shower and went to bed. Graphic thoughts of Catherine running through my mind.

Chapter 2:

Catherine had extracted my work e-mail address from me the night before while I had been frantically stroking my cock for her with her panties in my hand. That morning at work I had an e-mail sitting in my inbox. It was from Dirty666666@yahoo.co.uk, with a title "Pussy boy". I opened it worried what it would contain and worried if it had been picked up by our firewall.

"Hope you enjoyed last night", she wrote. "Come back round Friday night at 8pm. Bring YOUR panties. Hope you like the present pussy boy. Dirtybitch"

The "present" was a picture attachment, a close up of a woman's pussy, shaven and wet and very open. Clearly, it had recently been filled by something very large.

I quickly closed the e mail and hoped no one had seen.

I got to her flat at 8:30 because I was caught up having drinks. She seemed agitated that I was late. This time she had a rug in the middle of the floor, a small mirror and she was wearing a kimono.

"Have you got your panties?" I pulled them out of my pocket. "You should be wearing them, pussy boy" she snarled. "Put them on now!" Eager to get down to it I quickly stripped and slipped on the panties. They felt so good as the fabric clasped my already rigid cock.

Catherine, opened her robe, revealing a basque and suspenders, with a pair of black panties which opened up when her legs parted revealing her pink flesh. I couldn't wait. "Come" she said, as she proceeded to prepare four lines of coke on the mirror. She rubbed her finger in the coke and then pushed it into my mouth rubbing my gums. This woman was unbelievable. What would she not do. We both took a couple of lines after which she started rubbing my cock through the panties. Mixing with the alcohol I was soon on another plane. My head was swimming and I felt great. I was also as horny as a goat and my hands were searching out Catherine's pussy. When they alighted on her pussy I found it was shaved making my cock give a little twitch. Catherine ground her pussy into my hand. The drugs were hitting me really hard. My head was spinning. Catherine started asking me all these questions as she rubbed my cock through the panties. What do you like? What do you want to do to me? Do you want to fuck my ass? I bet you do. Do you like talking dirty? Do you want to lick my ass? Go on tell me everything.

My head was spinning. My cock was feeling electrified, super sensitive. I began mumbling, oh yes yes, but Catherine insisted she wanted details, so out came all my dirty fantasies. I told her I wanted to be made to lick her ass and then take her, to make her eat my cock, to be made to eat cock and maybe be fucked by a guy; to watch my fiancée getting fucked by a black guy and watching her being made to eat a girl out. It was all there out in the open. The third time I had met this woman I had confessed everything, my darkest secrets that my fiancée of 4 years knew nothing of.

I quickly came into the panties. Catherine then climbed on top of me, straddling my head telling me that I was her pussy boy and to get licking. My tongue shot out and went to work. I had always thought of myself as a good lover but Catherine always wanted more and demanded it from me. I bit her clitoris and pulled away from her then flicked it feverishly with my tongue. Soon my face was covered in her juices as she writhed on top of me squeezing my head with her thighs pushing her sex into my face.

After she came she ordered me to lie down and pulled my cock out of the side of the panties. She then sat on my face facing my feet and ordered me to lick her ass while she violently rubbed my hardening cock.

My tongue shot out searching for her hole. My cock was soon hard again. Catherine then climbed onto my cock and guided it into her ass. "Fuck me pussy boy" she whispered "fuck my ass with that tiny prick of yours". This went on and pretty soon after I came again my seed filling her. When Catherine got off, she squatted above my face and let the cum drip from her ass onto my face and some went my mouth.

When I left Catherine told me to think of her when I was screwing my fiancee next. To imagine my cock was in her ass pumping away. And she also told me I had to lick out my fiancée's pussy before I could cum again.

I felt used. It was great, it was electric. Over the next few days, Catherine would not get out of my mind. At work I would find myself thinking of her and my trousers would tent embarrassingly. It began to fill my dreams too. Deviant sex dreams. Often I would wake in the middle of the night with a rock hard cock. I would wake my fiancée and make passionate love all the time thinking of Catherine and what she would do next. Images of Catherine would run through my head each time I came in my fiancée's pussy. But our lovemaking changed. I wanted more. I introduced a little light bondage and tried to get her to have anal sex.

As my wedding approached I would see less and less of Catherine. I told her it could not go on.

Chapter 3:

In the July I married. I hadn't ended it with Catherine but just let it peter our, never responded to her calls. Marriage was great and my wife became less inhibited about our sex life. However, after 3 years our sex life was getting a little monotonous. I increasingly began thinking about Catherine until one day I called her out of the blue at her flat. She was in.

We talked about things but it was clear that she was really pissed off. This didn't stop her from walking over to me and rubbing my crotch. Soon I was hard and soon I was naked. Catherine placed some handcuffs on me and fixed a collar around my throat. She linked a leather lead onto a small ring on the collar. This was new territory for me, but I guess she had been spending her time thinking up new mind games.

I found myself blindfolded and kneeling on her bed. Catherine left the room but I could hear her talking to somebody on the phone. A few seconds later I felt her hand on my balls and cock, then I realised she was placing a tight band around my cock and another around my balls. She then took the lead and started whipping my ass with it. Not lightly or playfully but really hard. The pain was incredible. I tried to move away but to no avail. Soon my ass was covered in red welts. Catherine then must have picked up some cream and massaged it into my ass spending considerable time rubbing it into my asshole. I then felt something pressing into my ass, something hard and very large. It was a dildo. "Don't worry you will be taking bigger tonight, Pussy boy". I winced and tried to escape the incessant pressure as she pushed the dildo deeper into me. My cock and balls were twitching trapped in their retraining bands. This was extreme. I did not know how extreme this was yet to get.

She was pushing the dildo in and out of me, saying " how do you like that pussy boy? Do you like being fucked?"

I was now in some pain, sweat was dripping from my forehead and naked body was caked in sweat. My cock was ready to burst but the cock ring was preventing me from cumming. My ass was on fire from the whipping I received and my butt was home to what felt like a huge rubber dildo.

Then things changed. I heard someone else come into the room. My heart began to pound in fear.

"What's going on here then Catherine? Who is this guy?" a voice boomed.

"Roy meet my pussy boy, you know the one I told you about."

"This is the one that likes wearing panties, eating cock and licking assholes eh? Well you are going to get a chance to do that tonight cos you is gonna be my pussy boy, my fuck bitch." Roy boomed.

"My lovely Catherine here has told me how badly you treated her. Now this is payback time!"

I heard Roy walked over to me and his huge hand slapped my ass as he laughed. He then took hold of the dildo and began ramming it in my ass. "What is this sissy prick here? This dildo is about the size of your sissy cock pussy boy. Bet you can't even feel it in there" he laughed.

I told him to get away from me and let me go. This resulted in a sharp punch to my ribs. The air rushed out of me and I collapsed onto the bed. Roy grabbed my head and pulled me up, grabbing the blindfold from my head. I found myself faced with a huge black guy. He was easily 6' 4'' and his T shirt hardly concealed his rippling muscles, he was huge and I was scared.

Roy pulled me by my lead onto the floor. Dragging me like a rag doll. My shoulder hit the floor hard as my hands were cuffed behind my back. I winced with the pain but Roy kept on dragging me. Eventually he pulled me up so I was kneeling directly in front of the bulge in his trousers.

"You gonna love this pussyboy" as he undid his belt and his trousers dropped to the floor. I was faced with a pair of boxershorts that were clearly more than filled. He then turned around and pulled his shorts down and turned to face me. There an inch from my face was a huge black cock. Still flaccid it dangled down past a massive black sack and rested against the middle of his well muscled thigh. Roy took his cock in his hand and began to slap it across my face.

"You like this don't you pussyboy." It was a statement not a question. He could see that my cock was rigid, but still in that state it was only half the size of his flaccid black cock. His cock hit me again almost stinging my face. I could feel its weight as it hit me. It was heavy, a real monster and I was terrified. He then began to rub the cockhead against my lips.

"Come on, open up bitch!" Tears began to stream down my face. I felt trapped and humiliated. Catherine came around beside me and took the black cock in her hand, pulled the foreskin back and rubbed the smooth head into in my tears. She then put a hand behind my head and pushed my head forward.

"Take it pussyboy, open those sweet lips for me" she whispered "you know I know you want to."

My lips parted slightly and I could taste the slick juices covering his cockhead, tasting cock for the first time in my life. My tongue licked the tip tasting him, tasting his saltiness. With him pushing relentlessly into my face and Catherine pushing the back of my head I could do nothing but open up my mouth. I opened as wide as I could. The cockhead pushed hard against me and eventually slipped past my teeth. My mouth was stretched to its maximum as the cock entered me. But it carried on pushing through as it hit the back of my throat. I gagged but was trapped. With my hands cuffed behind me, unable to see because of my tears and unable to control what was being done to me, I felt completely defenceless. Hands pulling on my head and the huge cock pushing forward. I thought I was going to die. Roy then pulled back allowing me some relief before thrusting hard into my gaping mouth and slamming his cock against the back of my throat.

"Come on take it pussyboy" he hissed at me.

Catherine's hand took hold of my diminutive tool and began to stroke me. Her hand closed over my cockend gripping it and then opening as she slid it down the shaft. It was slippery and glistening with my juices betraying my excitement. As her hand slid down she twisted her wrist as she did so. It felt exquisite but all I could concentrate on was getting enough air as I was mouth fucked by this big black cock.

Eventually, Roy pulled his cock away from me and threw me onto the bed. Catherine and Roy then undid the handcuffs and fixed my arms to the top of the bed. Roy then pulled my left leg above my head to the side and tied it there. He proceeded to do the same with the other leg. This raised my ass off the bed and opened it for all to see. My hole exposed, my cock twitching with excitement. The ring around my balls squeezing them tightly. I needed to cum but I don't think that was part of the programme.

Roy knelt on the bed and moved towards me. He then placed our two cocks together laughing. His huge black beast against my tiny white cock and our balls touching. He stroked them together my precum and saliva mixing, "you like that bitch your little cock next to a real cock?" he laughed. He then took hold of his cock and aimed it at my virgin asshole. The head pressed against my most sensitive region. I could feel the immense insistent pressure as he pushed his considerable frame forward. Catherine watched from the side. Her excitement at the sight before her, clearly visible from her trance like stare as her fingers worked furiously on her swollen shaven pussy. I could see her juices running down between her thighs.