FabGuys.com forum: The making of a sissy

By *tephanie Somtimes OP TV/TS
3 weeks ago

South Derbyshire

I suppose looking back it all started at infant school. I preferred to play with the girls in the Wendy House than kick a ball around with the boys.

I used to keep a diary and would write things about the girls in it. I loved it when the girls chased me to try and see what I'd written about them. They would get me on the floor and sit on me so they could read the diary. Even then I liked to be dominated by girls.

After I got ready for school I would sit and chat with mum as she got ready. I watched carefully how she applied her make-up and how it transformed her looks.

I was fascinated with her seamed stockings and how she did up her suspenders. I would sit there and mimic what she was doing.

Then she would apply her nail varnish, I still remember the colour - rock on plum. I would ask if I could wear some but I was disappointed when she told me that boys didn't. I kept pestering her and she reluctantly agreed to let me put on some clear nail varnish.

I held my hands out with my fingers out stretched and carefully painted each nail. I loved it but later that day a girl at school noticed and she told her friends and they all started teasing me. It made me blush and I ran to the toilets to try and wash it off but of course it wouldn't come off. I felt embarrassed but I enjoyed the girls teasing me.

A few years later at Christmas my aunts and uncles came around to see us. My aunt Peggy loved fancy dress and asked me if I wanted to play dress up. I agreed and she took me up to mums bedroom to see what we could find.

We looked through mum drawers they were full of pretty clothes that I'd never seen her wear. My aunt found a old fashioned suspender corset and suggested I try it on.

I loved all the pretty lace, the straps and the suspenders. I slipped into it but it was miles too big but my aunt tightened the laces at the back so it didn't fall down. She found some of mum seamed stockings and she helped me on with those. Having watched mum so often I knew how to attach the suspenders.

I remember liking the tightness of the corset and how interesting all the straps and buckles were.

My aunt took me down stairs and I paraded around in front of the family. Dad was cross with my aunt but I love strutting around.

It was my first time dressed and I loved it and couldn't wait to try something else on of mums.

A few years later I found one of my dad's girly magazines. Inside was a woman dressed in a mink coat, on the next page she was standing with two men with the coat held open. She was just wearing lingerie underneath including stockings and suspenders.

The next time mum went out and left me on my own I headed for her bedroom. She had a fake mink coat and I knew she had some sexy lingerie as I'd seen it on a previous exploration.

I dressed just like the woman in the girly magazine and enjoyed a few minutes of being girly before mum got home again.

I was now in my mid teens and I still hadn't reached puberty. My best mate had already reached puberty, he had a deep voice and a big cock that he loved to show off.

It was about this time I became fascinated with men's bulges. My mates cock looked so powerful and made me feel quite weak in comparison. I still had a boys willy and it looked like that would change.

I did start to change but not in ways I was expecting. I developed puffy breasts and very sensitive pert nipples. My hips grew and I struggled to find school trousers to fit me. The man in the school uniform shop said I had hips and a bottom like a girl so I would need the next size up. I've never forgotten his comments.

At 18 I started dating a lovely girl, she was not a virgin like me and was quite forward. I remember her taking my hand and putting it up her blouse. I fondled her boobs like I was expected to do and she slipped her hand between my legs expecting me to be hard. Unfortunately I remained totally flaccid. This happened on a few occasions and the last time she started to cry. I didn't know what to say, what could I say, she did nothing for me.

I suppose I was lucky because girls did find me attractive whereas my mate was painfully shy around girls and didn't know what to do or say. He was having no luck either.

One day we were looking out of my bedroom window watching the girls leave the offices opposite. My mate kept making comments about them and then he grabbed my hips and pulled me into him.

He said, "If you were a girl I'd give you a good fucking".

I could feel his hard cock against my bottom and it really turned me on. Without thinking I pushed back against him and said, "I'll be your girl".

I rubbed my bottom up and down his groin it felt so natural. He undid his zip and slipped his cock out. I reached around and wrapped my hand around it. It felt amazing hot and so hard.

He reached around my waist and undid my belt and top button of my jeans and dragged them down around my ankles.

The cold air on my bottom felt so good and made me feel so vulnerable. I arched my back pushing my bum harder against his crutch. Without really thinking I began pinching my nipples as he rubbed his cock up and down my ass crack.

It didn't take long for him to cum and he exploded all over my peachy ass cheeks.

He walked away without saying anything.I pulled up my briefs and jeans. I loved that feeling of wetness and went downstairs.

He had gone, we never spoke about what happened and we never did anything again.

I knew from that day that I was a sissy.

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By *osportNewbieMan
3 weeks ago

Gosport

Good story, hope there's more to follow

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By *iller316Man
3 weeks ago

Alsager

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By *adbod69300Man
3 weeks ago

Manchester

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By *lare_thomas38TV/TS
3 weeks ago

my town

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By *erry55Man
3 weeks ago

Portlaoise

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By *issyJessicaTV/TS
2 weeks ago

Didsbury

Please write more...

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By *tephanie Somtimes OP TV/TS
2 weeks ago

South Derbyshire

Although I knew I was a sissy I persisted with my girlfriend.

What I did with my mate felt so natural whereas with my girlfriend it was an act. I remember her complaining that I was never hard. She either had to wank me or suck me to get me hard and then it didn't last long. Nevertheless we got married and bought a house together.

Right from the star we bickered, I don't think either of us was sexually fulfilled.

When doing some work in the airing cupboard I found two pairs of panties belonging to the previous lady of the house. They were so pretty, white satin with a powder blue lace trim. They were so unlike my wife's plain cotton panties. I took it as a sort of sign that I was indeed destined to be a sissy.

Things started to go wrong between me and my wife. Normally on her days off she would lounge around the house in just a t-shirt and panties, she never wore much make up.

Now when I got home from work she was fully made up as if she'd been out on the town. I quizzed her about it and she basically lied.

There were signs she was having an affair. We worked together and I felt sure she was having an affair with our mutual boss. At the time CB was very popular and she spent a lot of time chatting with a guy with the handle "The Impaler". I had an idea something was going on with him too.

Eventually we split up sold the house and got divorced. She had given me a bag of clothes to take down the tip. I was so excited to see what was inside. It turned out to be like a sissy lucky bag. There was some old make-up, panties, bra's, hosiery that I must admit had seen better days, skirts, dresses and suspender belts. It was like my birthday and Christmas had come together.

I found out later that there was a number of men that she'd been fucking. After an argument one night she told me her cunt was like a bucket and it was no thanks to me. It was like she was proud of the fact that she had become a slut.

To be honest I was quite jealous. I had fantasies about being a slut. I started hanging around public toilets and cruising places. I was too much of a wussy to do anything but being around other men in places like that excited me. Especially as under my male clothes I would wear some of her clothes.

I moved into a flat and was excited to be able to put my girly clothes in drawers and hand the skirts and dresses in the wardrobe. There was so much stuff my wife had thrown away. I was like a kid in a sweet shop.

I was holding up a lovely red dress, it was cut on the bias and had large black roses printed on it. It fitted me perfectly. I was just wondering whether to try it on or not when I heard a voice.

"I don't think that's your colour sweetie"

I turned around to see the lady from next door standing in the doorway of my bedroom. She was grinning from ear to ear and blushing almost as much as me.

She held out her hand and introduced herself as Deborah.

I shook her hand still in shock that she had just waltzed in. I tried to explain that I must of picked up the wrong bag but she just laughed.

She smiled and said when I had finished I should call around for coffee or a cold beer. She winked at me then left.

I sat down still in shock. In effect I had been caught. I wasn't sure if I should carry on hanging all my girly things in the wardrobe but I thought fuck it, it's my life and it would give me such a buzz seeing them in there each day so I did.

After I finished I decided to pop around to Deborah's for that drink. She opened the door and with a wicked smile said.

"I thought you might have dressed for me"

I went bright red and explained that my wife had asked me to take the bag down the tip and I just haven't had the time.

"Of course sweetie", she replied, "Whatever you say, come in".

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By *achealtvsubtoyTV/TS
2 weeks ago

hoddesdon

Fabulous

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By *iv JonesMan
2 weeks ago

Cardiff

More please Stephanie

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By *aleuk1965Man
2 weeks ago

newhall

Can't wait to see more 😊

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By *athyTV/TS
2 weeks ago

Nottingham

Hope there is more xx

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By *esley 60TV/TS
2 weeks ago

PERTH

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By *erry55Man
2 weeks ago

Portlaoise

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By *ikeC2012Man
2 weeks ago

Peterborough

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By *inkyKnicksTV/TS
2 weeks ago

Cupar

Loving this ❤️

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By *angerxxxMan
2 weeks ago

Loughborough

A sumptuous read

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By *illgossardTV/TS
2 weeks ago

Abergavenny Monmouth

Lovely, I hope there's more to follow

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By *tephanie Somtimes OP TV/TS
2 weeks ago

South Derbyshire

Although Deborah was younger than me it became obvious that she was more experienced. She had lost her virginity some time ago. Her husband was quite a flamboyant man who I hardly saw as he worked away for days at a time.

I noticed that while her husband was away she had a number of male callers. At the time she would of been about 23 but all the men were middle aged or older.

I had a liking for much older men too but I didn't realise girls were into older men.

One evening I went around to ask a favour. She barely opened the door and basically dismissed me. I heard a man ask who it was and she replied the tranny from next door. I was quite humiliated being dismissed and a little embarrassed that she was telling people about me.

The next day she was all friendly and apologetic. She asked if I would like to come over for dinner and I agreed.

We sat opposite each other chatting, the food was _errible but she was on top form flirting with me.

She wasn't the most attractive woman in the world so I could understand why she may have been easy. Even so she had a great figure and always seemed to have this naughty twinkle in her eye.

The top two buttons of her blouse were undone and her boobs were bubbling over the top of her push-up bra. She had a tight black pencil skirt on that hugged her sticky-out bottom.

She looked amazing but all I could think about was how much I would like to wear what she was wearing and go and walk down the high street.

After dinner we ended up on her sofa chatting. She remarked on the fact that her suspenders were showing through her tight skirt. I looked and smiled, I was totally out of my depth and didn't know what to do or say.

She took my hand and placed it on her leg and asked me if I could feel her suspenders. I was red as a beetroot but agreed I could feel them.

She gave me this look then took my hand and told me to come with her. She led me into her bedroom.

She dropped to her knees blushing with that irresistible twinkle in her eye and started kissing me through my trousers.

I was so nervous I just couldn't get hard. She undid my belt and zip and pulled my trousers down around my ankles. She carried on kissing me through my briefs. I'm sure most normal men would be rock hard by now but I remained totally flaccid.

She told me to step out of my trousers and take of my briefs and bend over the bed.

"Bend over the bed?", I asked nervously.

"Yes", she replied, "With your bum in the air.

I did as I was told, I felt incredibly vulnerable and started to get hard.

She came up behind me and reached between my legs and grabbed my cock, pulling it back between my ass cheeks.

At last I was beginning to get quite hard. Then to my absolute surprise she parted my ass cheeks and buried her head between them. Probing my hole with her tongue.

At the time I was an innocent 25 year old. It was the early 80's there was no internet, we were all quite naive. I'd never heard of rimming but that is what she did and I could tell she enjoyed it.

As she was licking and probing my ass with her fingers she was saying things like. "That's it sissy, open up for me"

She told me how many fingers she had inside me and soon there was four. She fingered fucked me with one hand while wanking me with the other.

My legs were trembling and I felt so deliciously vulnerable.

Then she said, "How would you like a man to come up behind you now and stick his big cock in your ass?"

I thought yes, yes but didn't dare say it.

She told me I was getting the gape and that my ass was as wet as a woman's cunt. I'd not heard the word before but I knew what she meant.

She took my hand and told me to finger myself. I reached around and slid a finger down the crack of my ass. Sure enough my ass was drenched, I could even feel it dripping down my leg.

Then she hit the spot that I now know was my prostate and I just exploded collapsing down on the bed exhausted.

Nothing like that had happened to me before. My head was spinning I didn't realise that such a young woman would be so adventurous, so naughty but she was.

I rolled over and couldn't bring myself to look her in the eye. I was embarrassed that I'd made it so obvious to her how much of a sissy I was.

There was a big wet patch at the end of the bed both from the cum that seemed to constantly drip from my cock and my ass that seemed to be so wet.

I went to pick up my trousers and briefs but she laughed and said. "Oh no, you're not going until you've finished me off"

She sat on the dry side of the bed and hitched up her pencil skirt and opened her legs. "Get your head under hear and lick my pussy".

Like an obedient little boy I did as I was told. It took ages to make her cum and I must admit I was getting bored but eventually she did and I was allowed to get up.

It was the most fun I'd ever had with a woman but it made me realise how much I wanted a man. I was just too much of a wussy to do anything about it.

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By *erry55Man
2 weeks ago

Portlaoise

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By *angerxxxMan
2 weeks ago

Loughborough

A sumptuous read

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By *erriTV/TS
2 weeks ago

Hastings St Leonards

I hope there is some more of your story because I really like it and I was getting turned on quite to know more of going on with you and your neighbor and did she help you out

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By *achealtvsubtoyTV/TS
2 weeks ago

hoddesdon

Well,,,lucky bastard !

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By *rianishardMan
2 weeks ago

Cambridge

Loving how this is developing. I can't wait to hear more x

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By *orkDefenderMan
2 weeks ago

Wakefield

The makings of a good story

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By *sissy-TV/TS
2 weeks ago

Gosprt

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By *ikeC2012Man
2 weeks ago

Peterborough

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By *harlotte39cdTV/TS
2 weeks ago

rochester

Love this, cant wait for more x

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By *emdad73Man
2 weeks ago

Wirral

More please!

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By *ackiex32TV/TS
2 weeks ago

Wick

Great story, very well written and a good pace xxx

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By *esley 60TV/TS
2 weeks ago

PERTH

Hope there is more

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By *ndstorm45Man
2 weeks ago

Wakefield

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By *tella tvTV/TS
2 weeks ago

Rosyth

More please x

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By *iller316Man
2 weeks ago

Alsager

Can't wait to hear more xx

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By *tephanie Somtimes OP TV/TS
2 weeks ago

South Derbyshire

The following week I didn't see much of Deborah because her husband was at home. It was pretty obvious that things were not good with them as I could hear them arguing.

The arguing culminated on the Friday night. I could hear doors slamming and furniture being moved around and then I heard the front door slam and it all went quiet.

On Saturday morning I walked passed Deborah's front door and she called me back.

Her eyes were puffy and I could see she had been crying. I comforted her and she asked me if I would like to come to dinner that night and I agreed.

We had another of her _errible meals and then went and sat on the sofa.

She started telling me her life story, how her father worked away and she never saw him. She said she had always been attracted to older men, father figures. She put this down to to her absent father.

I encouraged her to tell me about the men, not just their personalities but how big their cocks were and what she did in bed with them. At first she was reluctant but when I told her it was turning me on she put her hand between my legs. I think we were both surprised how hard I was and seeing this she became more graphic in her descriptions.

It was obvious that Deborah was a tart but a nice tart. She had a heart of gold.

She became more interested in my cock and undid my belt and zip and slipped her hand inside my briefs and started playing with me.

"Look at you", she laughed, "All hard like a real man"

She rested her head on my stomach and watched as she played with my cock.

I must admit I began to get bored and go soft but she obviously noticed and slowly her fingers drifted down to my bottom and that perked me up no end.

When I was hard again she grabbed my hand and lead me into the bedroom.

"I want you to fuck me".

"I'm not sure I can", I replied.

We kissed and I fondled her tits. She was very womanly and didn't do much for me at all. If I was going to pick a woman she would be small and petite, straight up and down with no curves, small boobies with pert nipples. Deborah was not like this at all.

I managed to stay hard enough to penetrate her but soon started to go soft.

As usual she knew what to do and slid her finger down my ass crack and started playing with my bottom. I got a little bit harder and was quite pleased that I was making her moan.

She got wetter and wetter and I couldn't feel much and began to lose interest.

She held my ass cheeks open and I could feel the cold air on my rosebud. Then she whispered in my ear.

"How would you like a man to come up behind you now and fuck you while you fuck me"

I didn't admit to anything but boy did I get hard.

She carried on.

"Can you imagine his big cock filling you up"?

"Grazing your prostate with his big knob, making you cum with each thrust"

With her fingers inside me I was loving it and able to stay hard with the thought of another man fucking me.

I managed to bring her off and she had a tremendous orgasm her whole body shaking.

I collapsed on the bed next to her and we had a cuddle and fell asleep in each others arms.

I was awoken about 30 minutes later, she was under the bed clothes sucking my cock and fingering my bottom.

I lay there enjoying it.

"Can you imagine if this was a man"? She asked, "His rough stubble rubbing against your smooth cock"

I didn't say anything, not wanting to admit that I was bisexual.

I don't know why but my ass always got wet when she fingered me. It was like I was designed to be fucked.

She worked on my prostate and I exploded into her mouth. She didn't flinch she had already told me how much she loved the taste of cum - dirty girl.

She appeared from under the bed clothes her face pink and flushed that naughty twinkle in her eye.

Then she kissed me, her full lips felt so soft. It was then I realised she still had a mouthful of my cum. I opened my mouth and the cum flooded onto my tongue. It felt so naughty, the taste was intense and the texture so smooth and silky.

At the time I was an innocent and didn't know it was called snowballing but that's what we did. She wanted me to swallow it but i wasn't sure. She told me not to be such as wussy so I did and I loved it.

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By *rianishardMan
2 weeks ago

Cambridge

Love this xx

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By *oxy4youTV/TS
2 weeks ago

Henfield

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By *teve carrickMan
2 weeks ago

Redhill

Perfect story

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By *erry55Man
2 weeks ago

Portlaoise

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By *iller316Man
2 weeks ago

Alsager

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By *harlotte39cdTV/TS
2 weeks ago

rochester

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By *esley 60TV/TS
2 weeks ago

PERTH

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By *D_SuckerTV/TS
2 weeks ago

Sileby

This is beautiful and so well written mmmmm

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By *ndstorm45Man
2 weeks ago

Wakefield

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By *MP GirlMan
1 week ago

Newcastle upon Tyne

Keep it cumming….please

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By *vsindyTV/TS
1 week ago

A place where sheep are warm, or Burnley.

Ahhh, the life story of a sissy.

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By *he WormMan
1 week ago

all over

More!!!! This is amazing x

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By *eemebabyMan
1 week ago

Dudley

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By *annasuckcockMan
5 days ago

ibstock

More please

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By *ameulTV/TS
5 days ago

norwich - ish

So horny!!!

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By *ilkyphoebeTV/TS
5 days ago

Biggleswade

Loving it

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By *ppleton70Man
5 days ago

Swallownest

What a great erotic story. Cannot wait for the next part.😄

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By *ikeC2012Man
4 days ago

Peterborough

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By *atnat54TV/TS
3 days ago

Bexhill-on-Sea

Wish I had a Deborah

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By *imale999Man
3 days ago

dudley

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By *tephanie Somtimes OP TV/TS
2 days ago

South Derbyshire

The next few months Deborah and I were like girlfriend and boyfriend.

I suppose we were both using each other. I was company for her and a bit of a sexual plaything, she was a trophy on my arm to show my friends. There was some talk about me being gay and Deborah helped squash those rumours.

She still carried on entertaining her men friends in the evening. There was at least three I knew of but even when we were out together she was always flirting.

Men seemed to know I was ineffectual and would flirt with her totally ignoring me like I wasn't there. It was humiliating but it left me under no illusions that I was a sissy regardless if I had a woman on my arm.

We'd go for drinks and days out into the countryside on a Sunday. I even took her to a works party, but she didn't behave there and showed me up.

One of my female work colleagues, Amanda came up to me furious that Deborah had been flirting with her husband. She told me to keep my woman under control else there would be trouble. I told Deborah but she just rolled her eyes and laughed.

One of the waiters was a middle aged Portuguese man, I could hear her giving him the come-on.

Then she disappeared and I went looking for her. I asked a mate and he said he thought he'd seen her with the waiter in the men's toilets.

This was not turning out how I imagined. Having Deborah on my arm was supposed to boost my ego and my standing with my work colleagues but instead she was making me look pathetic.

It was embarrassing asking people if they knew where she was but one woman took great delight in telling me she was outside with a man behind the refuse bins.

I went outside and there she was with her panties around her ankles her lovely dress hitched up being fucked by the Portuguese waiter up against the wall.

To be honest I was more concerned how it would look at work for me on Monday. It was like everyone knew my so called girlfriend was a tart.

Deborah saw me and waved me away and I headed back inside ashamed and embarrassed.

Eventually she came back inside and sat down with me like nothing had happened. I was so annoyed not because she'd fucked the waiter but because she had humiliated me in front of my friends.

She didn't care non of them were her friends, She told me to calm down and if I was a good little sissy I could lick her out later.

At the time I was furious and wouldn't entertain it but looking back now I wish she had pushed me under the table and made me do it there and then in front of my friends and work colleagues.

I would have especially liked my boss to see me. She and I had always held a flame for each other but she chose another work colleague over me.

Monday at work was so embarrassing my mates said they'd all fucked her too and the girls wouldn't speak to me.

I couldn't stay angry with Deborah for long, she told me not to be a wussy and that she was a tart but with a heart, which she was.

A few days later she invited me around for a another meal. She opened the door looking very sexy in a little peach skirt and matching blouse. I could see she wasn't wearing a bra as the material was hanging down and across from her nipples. She told me to go and sit in the lounge and she would join me with a glass of wine.

I walked into the lounge and was surprised to see a young man sitting there. I briefly said hello and went back into the kitchen.

I asked Deborah what was going on and she laughed.

"Go and chat with Josh", she said, "You'll like him, he's gay".

Once again I was furious with Deborah and she could tell.

"Stop being a wussy, it's rude to leave Josh on his own, go and chat with him".

I went back into the lounge and introduced myself to Josh and sat opposite him.

He was a lot younger than the men I'd fantasised about. I had a thing for dirty old men in their 60's and Josh looked younger than me.

The first thing I noticed was his big brown eyes. He was a big lad, a bit chubby, but I did have a thing for men with balloon bellies. I'm sure it's a sissy thing but they turn me on.

He was wearing a tight t-shirt and I could see he had defined man boobs and big nipples. Something I really liked.

Of course my eyes eventually settled on his bulge and I could see he had quite a girthy looking cock curled up down his leg.

Deborah wheeled her hostess trolley in, she loved entertaining and we sat and had our dinner. Josh turned out to be a nice guy and we all had a good chat.

For once it wasn't a bad meal and we sat back down with Deborah directing me to sit next to Josh on the sofa.

Deborah looked over at me beaming.

"Now you two have been introduced why don't you get to know each other better"

I looked over at Deborah in astonishment , what did she want us to do?

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By *andy71TV/TS
2 days ago

st helens

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By *sucker4DomsMan
2 days ago

Aberdeen

Just WOW!! Keep it up!!

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By *ub69bottomMan
2 days ago

Camberly

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By *erryBramleyTV/TS
2 days ago

Oh love it xxx

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By *azmin999jmMan
2 days ago

Wakefield

This is lovely

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By *ndrews642Man
2 days ago

exeter

Keep it going please

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By *erry55Man
18 hours ago

Portlaoise

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