She Found a Sissy
- 4 years ago
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I’m My Wife’s Sissy free porn video
My story starts 2yrs ago when l retired early from work, also at that time l was having trouble with my sex life, so went to see a doctor who informed me l was going through what he described as a male menopause which l never knew existed. My scrotum had shrunk and looked like a shrivelled ping-pong ball, my penis had retreated into my balls and could only be seen if l got an erection which measured almost an inch and with a cock that size l was finding it impossible to please my wife Jolie, so brought a strap-on, but l could see this wasn’t giving the enjoyment Jolie was used to getting, so our sex life took a steep nose dive.
I was online when l came across an article about dogging, when my wife came home from work l brought up the subject and suggested we try one of the local carpark which apparently was a meeting place. First Jolie thought me mad, but when we were in bed she said may be if we went for a drink before going to the carpark, then decided we would try dogging the following Friday evening.
Friday evening came l sat downstairs while Jolie dressed, l have to say she dressed to be noticed. Her top was a blue see through blouse that showed off the white uplifting bra underneath with a skirt just above the knee that had a split either side that ended about 9” below the waist band of her skirt, Jolie asked if she went to high with the splits, l nodded and remarked she looked fantastic and if l could have l would have fucked her there and then.
We drove to a little pub outside town for a drink there wasn’t a male head that didn’t turn to follow my wife from the entrance to the table which made her blush, but after a few wines Jolie became relaxed and even flirted a little when she went to the toilets before we left.
We arrived at the carpark and parked in one corner there were two cars next to each other, me and my wife both had butterflies. One of the cars put their indicators on, so l did the same, he came and parked my side of the car and asked if we were playing, l nervously explained it was our first time then realised what an idiot l must have sounded. The guy introduced himself as Martin, laughed and said “we all have to start somewhere” then got out of his car and went to Jolie’s window and l left them to chat as she seemed to be enjoying the attention.
Martin asked if he could feel her tits then slid his hand down her blouse, Jolie closed her eyes and sat back in her seat, soon her tits were out and he was leaning in the window sucking her nipples. Jolie didn’t need much persuasion to get out the car and when l got out she was in a passionate embrace with Martin kissing, his hand was now up her skirt and she was eagerly wanking his large thick shaft, Jolie glanced over at me and remarked “l’m going to get a real cock” and whispered something to Martin. He opened our car backdoor; Jolie climbed in and lay on her back then raised her skirt and wriggled out of her knickers, lifted her legs and Martin got into the back between Jolie’s spread legs and slid his shaft inside my wife’s pussy hole, the further he sunk his cock the louder Jolie’s cries became which were then muffled by Martin’s mouth on my wife’s mouth. I stood outside the car watching his buttocks lifting up and down every so often Jolie would let out a moan or groan telling Martin how good his cock felt wedged up inside her. He loudly declared he was going to deliver his hot sticky liquid, l heard Jolie gasp as he thrust downward the pair both whimpering and grunting as they stay locked together.
After another long passionate kiss Martin climbed from between my wife’s legs, he asked if l was going to now fuck her, before l could answer Jolie announced l didn’t have a cock it was more like a maggot then laughed adding a maggot was bigger, l could see Martin wanted to comment, but instead asked my wife when was she coming to the carpark again, Jolie answered soon and hoped Martin would be there they kissed and he said “thank you” before going back to his car. Jolie got into our car a lot less nervous than when she got out and we left for home.
We got home and l sat in the lounge my wife changed into her bathrobe then came into the lounge still quite merry from the wine and the fuck. She became quite abusive telling me l needed a cock to be a man then opened her robe, spread her legs and stretched her pussy lips to show me Martin’s creamy sticky load, Jolie’s inner pussy lips glistened from Martin’s spunk she even had cum over her pussy hairs, she accused me of being a sissy, her sissy and ordered l lick her pussy clean because that’s what sissy’s do. Jolie in a raised voice, shouted “come on, clean me!”, l slid from the armchair l was sitting in and crawled over to where she sat with her pussy spread, Jolie positioned herself on the edge of the sofa cushion and l put my head between her legs, l could smell the strong odour of Martin’s spunk and my wife’s juices on her pussy.
I ran my tongue between Jolie’s pussy, she let out a gasp it was the most excited l had got my wife in years so did it again this time harder, her clitoris became erect, l sucked her furiously she grasped the back of my head and pushed my whole face against her sticky pussy. Jolie had now began shouting “lick me sissy, lick me” then she did something Jolie had never done before she squirted straight into my mouth and face l couldn’t move because of the tight hold she had on the back of my head. I was ordered to carry on sucking as she raised her hips and wriggled on my tongue, the taste of Martin’s deposit in my wife wasn’t as bad as l imagined, l was enjoying myself hearing my wife have orgasm after orgasm.
All of a sudden Jolie let out one almighty cry and yelled “you bastard” as her orgasm exploded, she was panting, gasping trying to catch her breath, l kissed my way up to her tits she lifted my head and in no uncertain terms told me “that’s enough sissy get off me”, l was pushed to one side and told she was going to bed and it would be better if l slept in the spare-room till she needed me again. Jolie got from the sofa and left me kneeling on the floor in the lounge.
At breakfast l knew Jolie wasn’t herself she seemed to look down on me, l wasn’t asked l was told that she wanted the washing done and when l remarked what happened to ‘please and thank you’ she snapped l was her sissy and cockless sissy’s like me do as they’re told. I wasn’t scared, but she was more well-built them me and could give a hard wallop if she wanted, Jolie was 5 inches taller than me and that has always been the joke even when we first met, she would carry me over the fresh-hold because l’m not the athletic sort.
All that morning l was thinking of the previous night, Martin fucking my wife and me between her legs l was getting quite excited even my little maggot as Jolie calls it decided to appear all near one inch of him. I looked down at the wash basket and saw a pair of my wife’s knickers as for what happened next l really don’t know how it happened, l found myself going through Jolie’s knicker draw to find a pair of knickers to wear, next came a bra then l tried on an array of skirts, but found a dress which felt more comfortable, l spent the rest of the day dressed in Jolie’s clothes.
That evening we had our meal then Jolie had a bath and we sat watching telly, she had a few glasses of wine then at around 9.30pm Jolie announced she was going to bed, l asked if she wanted me to do anything, hinting at another tongue licking. Jolie gulp the last of the wine from her glass and informed me, she will tell her sissy when he is needed then gave me permission to wank myself off and crawly added, oh you need a cock to do that, she put her glass down and went to bed.
For about a week l had been changing into Jolie’s clothes and got on with the housework then one day the doorbell rang and without thinking l answered the door, it was Alice our neighbour, she was a pair shaped woman in her late 60s. I had forgotten all about being dressed in Jolie’s clothes it was only when her smile turned to a bewilderment that l realised, Alice handed me a letter saying the postman delivered it to her house by mistake then turned and almost ran down the path.
It was about 40 minutes later the bell rang again this time l asked who it was before opening the door, a soft whisper replied “me Alice” there was no point in me going to get changed, so l opened the door. Alice was clutching a bottle of wine, “can l come in” she asked, she followed me into the kitchen, we sat down and Alice opened the bottle, l put two glasses on the worktop which she then filled. We both took a sip l put my glass down and Alice came straight out and asked why do l wear women’s clothes, l decided to tell her about my sex problem and dressing up was how l now got my thrills, l could see she didn’t believe me about what the doctor called a male menopause that was when the questions started like why couldn’t l take hormone patches, so l explained male menopause wasn’t quite like a females and joked would she like to see my shrivelled balls and little cock to prove it, Alice giggled and declined my offer.
We had a few more wines and Alice declared if l was to dress like a woman then l needed her to show me how to sit and how to walk, the wine was going well. It was strange Alice had been a neighbour for 14 years and in all that time this was the first time that we had actually really spoken; l opened another bottle and our inhibition’s went out the window and the discussion got more frank.
Alice asked if l found knickers uncomfortable as the crutches wasn’t like boxers, l reminded her they would be if l had something there and gave her a quick flash under my dress, she put her glass down and said “show me” then egged me to show her. I was brave enough thanks to the wine l had drunk, so getting to my feet l lifted my dress and pulled down my knickers, Alice looked between my legs, “you’ve got no cock” she declared then pointed at my shrivelled ball sack and asked if she could touch it, l thrust my hips forward and said “go on then”, Alice cradled my balls in the palm of her hand and remarked how l felt warm and rubbery then gently slid her hand back and forth, the next thing l knew she had a very tiny amount of liquid in her hand, Alice smelt her palm and stated l had ejaculated, she put a finger into my spunk and began spreading it in her palm, l apologised and passed her a tissue.
I pulled my knickers up and sat down Alice wiped her hand and told me to sit correctly, l was to sit up not slouch then she got me to walk with her behind me and swing my bum like a pendulum, the sitting l found a lot easier than the walking. I was really enjoying having Alice teaching me how to be a woman, it felt nice being dressed in my wife’s clothes and feel another woman touching me and l think Alice felt the same.
Alice was showing me how to squat in a dress without showing off my knickers when she lost balance, l helped her up and she went to give me a kiss on the cheek to thank me, but l turned my head. I could feel Alice’s breath on my face, l shouldn’t have but l kissed her, she didn’t pull away, but then realised what we were doing a pulled away, l immediately said how l had over stepped the mark, Alice nervously blurted out she had to go as it was getting late, grabbed her cardigan and was gone.
I went into the kitchen rinsed out the wine glasses and put the bottles in the bin, it wasn’t that late and my wife Jolie wouldn’t be home till 5.30pm, so l could have a lie down, l lay on the bed thinking how l had messed it up with Alice, it wasn’t long before l drifted off to sleep.
I was woken by my wife Jolie screaming at me, l had fallen asleep still dressed in her clothes she was holding a black sack filled with my shirts, pants, socks and trousers, she was telling me if l wanted to wear her clothes then l can wear them, but she was throwing out all my clothes. My head was spinning, Jolie left the bedroom and l followed, she was in what used to be our bedroom putting knickers, bras skirts, tights, tops and dresses onto the bed, l was ordered to take the clothes and put them into the room l had been sleeping in then l was to meet her downstairs.
When l walked into the lounge Jolie was sat holding a glass of wine, l was about to sit down when she snapped “l didn’t tell you to sit down”, l stood there like a naughty boy, she took a sip of wine and asked “so you want to be a sissy”, and before l could answer she stated firmly, l was to be her sissy then hitched up her skirt and ordered l was to take down her knickers and clean her sticky hole as Graham a young doctor at the hospital had given her a good fucking in the back of his car before she came home.
Getting to my knees in front of her, l took hold of her knicker waist band and eased then down to her ankles then off, Jolie told me to lick the crutch, l held her knickers to my face and could smell the strong odour of seaman, “lick it” she screeched, l poked out my tongue and slid the crutch of her knickers down my tongue. The seaman taste sent a tingling through my whole body l felt my own watery spunk dribbling down my inner thigh, Jolie spread her legs and ordered l clean her, l got straight on with the job, burying my tongue between her sticky pussy lips, Jolie’s clitty started to swell, so l began sucking her clitty hard she yelled “don’t fucking stop, don’t you fucking dare” and pushed on the back of my head hard into her moist sticky pussy.
I gently bit on her clit this caused Jolie to cry out calling me a dirty whore, she thrust herself against my mouth and squirted, she had such a tight hold on my head l couldn’t move her gush squirted into my mouth, “drink me sissy, swallow it all” Jolie hissed.
Once she recovered from her orgasm Jolie got to her feet and said she was going for a bath and l was to clean up the wet patch on the sofa cushion and carpet because she was bringing a friend home the following evening and didn’t want the room smelling, before going for her bath Jolie informed me we were going shopping in the morning as she wasn’t sharing her clothes with a dirty little sissy, and left the room.
The next day we had breakfast then left for the shops l felt sick the closer we got to the shopping centre, my wife parked l got out the car and froze, she cruelly told me there was no point in hiding l had to go out sometime then announced that’s she couldn’t call me little sissy when we were out and asked if l liked the names Cloe, Rose or Cindy, l replied Cloe sounded nice Jolie nodded and said we were going to get me underwear first then scout a few charity shops for dresses, skirts and tops she turned and walked towards the centre as l followed l could feel the eyes burning into me.
Getting my underwear didn’t take long as my wife brought me plain simple bras and smart cotton knickers which l called Bridget Jones knickers, she gave me a glare and whispered “my sissy will wear what l say” then gave me a false smile before saying, Cloe l bet you can’t wait to get home and try your new undies on, well Jolie was half right l couldn’t wait to get home. She must have dragged me into every charity shop to buy all the old-fashioned clothes she could find, in one of the charity shops Jolie brought me a ginger wig to finish off my wardrobe then thankfully we went home.
When we got home, Jolie told me to change out of her clothes and warned me never wear her clothes again. I went to my room and redressed the bra l padded with loo roll and my knickers were a bit tight the white blouse and blue skirt fitted well, l looked at myself in the wardrobe mirror and fixed the ginger wig then l ventured downstairs dressed as my wife’s sissy Cloe.
Jolie was sat at the kitchen table, she told me to turn around for an inspection and explained the person coming for a drink was Martin the bloke we first met dogging. They had been meeting after work so he could fuck her, Jolie justified their fucking behind my back as my fault due to me having a tiny cock and not being able to produce a healthy load of cum.
Before Jolie’s guest arrived she put makeup on me then l had my orders for the evening which were basically l could be seen, but not heard. Jolie had drank almost a bottle of wine when the door-bell rang, so l went to let Martin in. I had forgotten how he was over 6ft with broad shouldered and l have to admit me being 5ft-6 with a slim frame l felt small standing in front of him. I showed Martin into the lounge and he commented on my dress, Jolie told him l was her sissy and she had named me Chloe, then added to be a man you need a cock and spunk filled balls and this sissy has neither, the pair laughed.
It wasn’t long before they were taking each other’s clothes off, l was sat in the corner every so often Jolie would meet my eye and make a sarcastic comment when wanking Martin by telling me it is a shame l never had a real cock like Martin’s then sucked his balls and with her mouthful Jolie would tell me how she couldn’t wait to get his steaming hot creamy spunk inside her.
They were both naked on the floor, Martin was propped up against the sofa and Jolie had her head between his legs wanking and sucking his cock, l could hear the slurping and sucking sound she was making. Martin had his head tilted back sighing and groaning as my wife worked on his hard shaft, l have to say l was beginning to find watching them was turning me on then Martin shouted “l’m cuming” and pushed my wife’s head downward so she had no option but to take his hot creamy sticky load straight down her throat, l also felt a warm dampness in the crutch of my knickers, it was my own tiny amount of cum there wasn’t enough to keep my wife or any woman happy, but l felt quite proud at shooting something.
After Martin shot his load down my wife’s throat she lay between his legs her hand firmly gripping his shaft to slowly wank him, Martin looked over at me then bushed his hand through Jolie’s hair and told her to work on his cock because he was going to give her a good fucking since her sissy husband couldn’t, Jolie took a sip of wine then l watch her lower her head and swallow up Martin’s shaft into her open mouth.
He put a hand either side of Jolie’s head and began slamming it downwards onto his cock then placed a hand onto her bum and rammed a finger into her arse hole, Jolie gave-out a little cry and worked her mouth faster on Martin’s shaft. He must have been near to emptying his balls once more because he yanked Jolie’s head up and she lay on her back with legs spread wide, Martin got into position between her legs clutching his hard cock and fed the whole shaft fully inside my wife’s eagerly waiting pussy. As they fucked each other all l could hear was their grunting and heavy breathing every so often Jolie would yell “harder baby, harder!”, Martin just let out “ugh, ugh yeses” as he rammed his thick rock-hard shaft deep into my wife’s hole.
Jolie was panting which got louder and louder, she was starting her orgasm; l knew this sound from when l’ve had to lay next to her in bed while she fucked herself with a rabbit.
From where l was sitting l got a good view of Martin’s thick shaft sliding in and out of my wife like a mechanical piston which all of a sudden increased it’s speed then her pussy swallowed the whole length and Martin yelled “oh baby, l’m gonna flood your tubes” and held his shaft firmly inserted between Jolie’s pussy lips filling her with his sticky love liquid, she dug her nails into his back leaving scratches like whip marks. Their panting and groaning subsided and they lay joined together in a sweaty heap, after a long kiss Martin lifted himself from between my wife’s legs and sat against the sofa the head of his cock had a covering of spunk.
Jolie lay on her back with her legs still spread, she half sat up and ordered l make myself useful and clean her dribbling sticky pussy, Martin had indeed filled my wife with a very full thick load, Jolie pulled my head into her hole and as l thirsted on Martin’s spunk she told me that Martin was now the man of the house, l finished cleaning my wife’s pussy and about to return to my seat when Jolie ordered that her lover would like to be cleaned and gave a little laugh, Martin held his cock and rolled his foreskin down. I crawled between his legs gripped his shaft and began licking his urethral opening, Jolie pushed the back of my head forcing Martin’s cock down my throat, “suck it!” she demanded. His cock tasted very salty, l found myself enjoying the flavour and the smoothness on my tongue, my wife ripped my head up and told me to go sit down.
They fucked each other another 4 time with me cleaning them both afterwards, l thought Martin might have stayed the night, but he had to get home to his wife. It was nearly midnight when he left in a taxi, my wife Jolie went to her room and l went to mine.
When l got up the next morning Jolie had gone to work there was a shopping list on the table, l told myself l had to go out sometime on my own and it wasn’t a big list so l could get what we needed at the minimart two roads away.
About 10am Alice knocked at the door as soon as l saw it was her l was about to apologise for the kiss we had, but she stopped me and explained why she dashed off, it was because Alice enjoyed us kissing, but felt guilty as she had only ever kissed her husband in such a sexual way. What she said sent cross messages to me, did Alice mean she wanted us to go further or just forget what happened, anyway for now l was happy she was still talking to me and we sat down to have a coffee. I was telling her that my wife Jolie had left me a shopping list,, but was nervus to go out, so Alice said she will come with me which was a great relief to hear.
The shopping trip with Alice wasn’t so bad as l imagined and we were really getting on, she kept reminding me to walk like a woman, when we returned Alice invited me into her house for a coffee, but that was replaced with a glass of wine.
Our conversation got around to my wife Jolie and what she thought of me as a woman, l don’t know why but l began telling Alice about Martin and Jolie, Alice put her hand on my knee and said she thought l looked wonderful then asked me to kiss her, her lips met mine our tongues entwined and we both sank back in the sofa.
I got my hand under her skirt and into Alice’s knickers, her pussy was very bushy, l whispered “l want to eat you”, she answered by opening her legs which spread her 60-year-old pussy lips, Alice’s clitoris had swollen and protruding from between her lips l gently rubbed my thumb over her clit she let out a gasp. I lowering myself into position and peeled down her knickers, put my mouth over Alice’s clit and started sucking her, she was pushing her crutch against my mouth whimpering, her love juices began to low like a babbling brook Alice was soaking me.
We moved to the floor l raised her legs and really wet to work on her pussy, she wriggled and squealed, l removed my knickers and we got into a scissor position the feeling was fantastic l rubbed my small dried-up wrinkled scrotum hard against Alice’s dribbling pussy even l started groaning, she began shacking and shrieked “oh yeses” then lay on the floor panting. When Alice caught her breath, she exhaled and confessed that was the first orgasm she had ever had as sex with her husband was once a month and anniversaries, it had been this way since they got married 42 years ago. That afternoon we taught each other many things and l don’t think Alice nor l had ever had such a wonderful few hours.
I had been dressing as a woman for 5 months, l didn’t need to wear wigs as my hair had grown and Alice’s training had helped me look more passable as a woman, my wife was bringing home different men, but Martin was her most regular.
One lunchtime Martin knocked at the door l explained my wife Jolie wasn’t home, but he still wanted to come in, so we went into the kitchen and l started to make us a drink when Martin grabbed me from behind turned me around and kissed me, l was powerless to do anything he was much stronger than me, Martin was over 6ft and broad shouldered compared to me at 5ft-6 with a thin frame. Next l was leant over the table and held in place by his large hand at the back of my neck, my skirt was wrenched up and my knickers ripped off, Martin declared he had never fucked a sissy.
I felt the warm head of his cock passing between my bum cheeks then my arse hole being stretched by the head of Martin’s cock, slowly his shaft sank further inside me the pain wasn’t unbearable, but extremely uncomfortable, my god Martin did have a thick hard cock.
When his hard rod was fully inside me he took hold of my hips, “ready sissy bitch” he asked and began fucking me hard and fast, l don’t know what happened, but the thrill of being fucked began to get me very aroused and l found myself pushing backwards to meet Martin’s forward thrusts. He must have been near to emptying his sticky load, l swear the head of his cock inflated just before he yelled “oh fuck yeah” and gave one hell of a thrust into my arse. I screamed with excitement as l felt Martin’s creamy hot stream of spunk flow from his urethral opening, once he delivered the payload he began giving little jerks into my hole then before sliding his cock from me Martin remarked “you’re nice and tight”, he slapped my bum and dressed where as l lay across the table well and truly fucked with a creampied arse hole, but l felt bloody good, it was about 20 minutes before l went to clean myself. I didn’t feel my wife Jolie needed to know about my visit from her lover as l knew Martin was going to make many more quick visits.
My wife Jolie came home and announced she was taking me to an Ipswich hospital to see a cosmetic surgeon, she wanted me to have breast implants and to get something done with my dried-up shrunken scrotum between my legs, it was made clear l didn’t have a say in the matter, but l didn’t really mind because l was enjoying my new life as my wife’s sissy.
It was a quiet drive to the hospital and the surgeon was a nice woman l didn’t do much talking as my wife basically told the doctor she wanted me to have breast and my balls removed. I was stripped and examined it was then the doctor declared she couldn’t give me the cut as my cock was to small so couldn’t insert it inside me to make a vagina, but she could shape my scrotum to look like vagina lips, but before any implants and operation l was put on hormone treatment.
I shall write how my hormone treatment went and what happened on the return visit to the Ipswich hospital.
I was online when l came across an article about dogging, when my wife came home from work l brought up the subject and suggested we try one of the local carpark which apparently was a meeting place. First Jolie thought me mad, but when we were in bed she said may be if we went for a drink before going to the carpark, then decided we would try dogging the following Friday evening.
Friday evening came l sat downstairs while Jolie dressed, l have to say she dressed to be noticed. Her top was a blue see through blouse that showed off the white uplifting bra underneath with a skirt just above the knee that had a split either side that ended about 9” below the waist band of her skirt, Jolie asked if she went to high with the splits, l nodded and remarked she looked fantastic and if l could have l would have fucked her there and then.
We drove to a little pub outside town for a drink there wasn’t a male head that didn’t turn to follow my wife from the entrance to the table which made her blush, but after a few wines Jolie became relaxed and even flirted a little when she went to the toilets before we left.
We arrived at the carpark and parked in one corner there were two cars next to each other, me and my wife both had butterflies. One of the cars put their indicators on, so l did the same, he came and parked my side of the car and asked if we were playing, l nervously explained it was our first time then realised what an idiot l must have sounded. The guy introduced himself as Martin, laughed and said “we all have to start somewhere” then got out of his car and went to Jolie’s window and l left them to chat as she seemed to be enjoying the attention.
Martin asked if he could feel her tits then slid his hand down her blouse, Jolie closed her eyes and sat back in her seat, soon her tits were out and he was leaning in the window sucking her nipples. Jolie didn’t need much persuasion to get out the car and when l got out she was in a passionate embrace with Martin kissing, his hand was now up her skirt and she was eagerly wanking his large thick shaft, Jolie glanced over at me and remarked “l’m going to get a real cock” and whispered something to Martin. He opened our car backdoor; Jolie climbed in and lay on her back then raised her skirt and wriggled out of her knickers, lifted her legs and Martin got into the back between Jolie’s spread legs and slid his shaft inside my wife’s pussy hole, the further he sunk his cock the louder Jolie’s cries became which were then muffled by Martin’s mouth on my wife’s mouth. I stood outside the car watching his buttocks lifting up and down every so often Jolie would let out a moan or groan telling Martin how good his cock felt wedged up inside her. He loudly declared he was going to deliver his hot sticky liquid, l heard Jolie gasp as he thrust downward the pair both whimpering and grunting as they stay locked together.
After another long passionate kiss Martin climbed from between my wife’s legs, he asked if l was going to now fuck her, before l could answer Jolie announced l didn’t have a cock it was more like a maggot then laughed adding a maggot was bigger, l could see Martin wanted to comment, but instead asked my wife when was she coming to the carpark again, Jolie answered soon and hoped Martin would be there they kissed and he said “thank you” before going back to his car. Jolie got into our car a lot less nervous than when she got out and we left for home.
We got home and l sat in the lounge my wife changed into her bathrobe then came into the lounge still quite merry from the wine and the fuck. She became quite abusive telling me l needed a cock to be a man then opened her robe, spread her legs and stretched her pussy lips to show me Martin’s creamy sticky load, Jolie’s inner pussy lips glistened from Martin’s spunk she even had cum over her pussy hairs, she accused me of being a sissy, her sissy and ordered l lick her pussy clean because that’s what sissy’s do. Jolie in a raised voice, shouted “come on, clean me!”, l slid from the armchair l was sitting in and crawled over to where she sat with her pussy spread, Jolie positioned herself on the edge of the sofa cushion and l put my head between her legs, l could smell the strong odour of Martin’s spunk and my wife’s juices on her pussy.
I ran my tongue between Jolie’s pussy, she let out a gasp it was the most excited l had got my wife in years so did it again this time harder, her clitoris became erect, l sucked her furiously she grasped the back of my head and pushed my whole face against her sticky pussy. Jolie had now began shouting “lick me sissy, lick me” then she did something Jolie had never done before she squirted straight into my mouth and face l couldn’t move because of the tight hold she had on the back of my head. I was ordered to carry on sucking as she raised her hips and wriggled on my tongue, the taste of Martin’s deposit in my wife wasn’t as bad as l imagined, l was enjoying myself hearing my wife have orgasm after orgasm.
All of a sudden Jolie let out one almighty cry and yelled “you bastard” as her orgasm exploded, she was panting, gasping trying to catch her breath, l kissed my way up to her tits she lifted my head and in no uncertain terms told me “that’s enough sissy get off me”, l was pushed to one side and told she was going to bed and it would be better if l slept in the spare-room till she needed me again. Jolie got from the sofa and left me kneeling on the floor in the lounge.
At breakfast l knew Jolie wasn’t herself she seemed to look down on me, l wasn’t asked l was told that she wanted the washing done and when l remarked what happened to ‘please and thank you’ she snapped l was her sissy and cockless sissy’s like me do as they’re told. I wasn’t scared, but she was more well-built them me and could give a hard wallop if she wanted, Jolie was 5 inches taller than me and that has always been the joke even when we first met, she would carry me over the fresh-hold because l’m not the athletic sort.
All that morning l was thinking of the previous night, Martin fucking my wife and me between her legs l was getting quite excited even my little maggot as Jolie calls it decided to appear all near one inch of him. I looked down at the wash basket and saw a pair of my wife’s knickers as for what happened next l really don’t know how it happened, l found myself going through Jolie’s knicker draw to find a pair of knickers to wear, next came a bra then l tried on an array of skirts, but found a dress which felt more comfortable, l spent the rest of the day dressed in Jolie’s clothes.
That evening we had our meal then Jolie had a bath and we sat watching telly, she had a few glasses of wine then at around 9.30pm Jolie announced she was going to bed, l asked if she wanted me to do anything, hinting at another tongue licking. Jolie gulp the last of the wine from her glass and informed me, she will tell her sissy when he is needed then gave me permission to wank myself off and crawly added, oh you need a cock to do that, she put her glass down and went to bed.
For about a week l had been changing into Jolie’s clothes and got on with the housework then one day the doorbell rang and without thinking l answered the door, it was Alice our neighbour, she was a pair shaped woman in her late 60s. I had forgotten all about being dressed in Jolie’s clothes it was only when her smile turned to a bewilderment that l realised, Alice handed me a letter saying the postman delivered it to her house by mistake then turned and almost ran down the path.
It was about 40 minutes later the bell rang again this time l asked who it was before opening the door, a soft whisper replied “me Alice” there was no point in me going to get changed, so l opened the door. Alice was clutching a bottle of wine, “can l come in” she asked, she followed me into the kitchen, we sat down and Alice opened the bottle, l put two glasses on the worktop which she then filled. We both took a sip l put my glass down and Alice came straight out and asked why do l wear women’s clothes, l decided to tell her about my sex problem and dressing up was how l now got my thrills, l could see she didn’t believe me about what the doctor called a male menopause that was when the questions started like why couldn’t l take hormone patches, so l explained male menopause wasn’t quite like a females and joked would she like to see my shrivelled balls and little cock to prove it, Alice giggled and declined my offer.
We had a few more wines and Alice declared if l was to dress like a woman then l needed her to show me how to sit and how to walk, the wine was going well. It was strange Alice had been a neighbour for 14 years and in all that time this was the first time that we had actually really spoken; l opened another bottle and our inhibition’s went out the window and the discussion got more frank.
Alice asked if l found knickers uncomfortable as the crutches wasn’t like boxers, l reminded her they would be if l had something there and gave her a quick flash under my dress, she put her glass down and said “show me” then egged me to show her. I was brave enough thanks to the wine l had drunk, so getting to my feet l lifted my dress and pulled down my knickers, Alice looked between my legs, “you’ve got no cock” she declared then pointed at my shrivelled ball sack and asked if she could touch it, l thrust my hips forward and said “go on then”, Alice cradled my balls in the palm of her hand and remarked how l felt warm and rubbery then gently slid her hand back and forth, the next thing l knew she had a very tiny amount of liquid in her hand, Alice smelt her palm and stated l had ejaculated, she put a finger into my spunk and began spreading it in her palm, l apologised and passed her a tissue.
I pulled my knickers up and sat down Alice wiped her hand and told me to sit correctly, l was to sit up not slouch then she got me to walk with her behind me and swing my bum like a pendulum, the sitting l found a lot easier than the walking. I was really enjoying having Alice teaching me how to be a woman, it felt nice being dressed in my wife’s clothes and feel another woman touching me and l think Alice felt the same.
Alice was showing me how to squat in a dress without showing off my knickers when she lost balance, l helped her up and she went to give me a kiss on the cheek to thank me, but l turned my head. I could feel Alice’s breath on my face, l shouldn’t have but l kissed her, she didn’t pull away, but then realised what we were doing a pulled away, l immediately said how l had over stepped the mark, Alice nervously blurted out she had to go as it was getting late, grabbed her cardigan and was gone.
I went into the kitchen rinsed out the wine glasses and put the bottles in the bin, it wasn’t that late and my wife Jolie wouldn’t be home till 5.30pm, so l could have a lie down, l lay on the bed thinking how l had messed it up with Alice, it wasn’t long before l drifted off to sleep.
I was woken by my wife Jolie screaming at me, l had fallen asleep still dressed in her clothes she was holding a black sack filled with my shirts, pants, socks and trousers, she was telling me if l wanted to wear her clothes then l can wear them, but she was throwing out all my clothes. My head was spinning, Jolie left the bedroom and l followed, she was in what used to be our bedroom putting knickers, bras skirts, tights, tops and dresses onto the bed, l was ordered to take the clothes and put them into the room l had been sleeping in then l was to meet her downstairs.
When l walked into the lounge Jolie was sat holding a glass of wine, l was about to sit down when she snapped “l didn’t tell you to sit down”, l stood there like a naughty boy, she took a sip of wine and asked “so you want to be a sissy”, and before l could answer she stated firmly, l was to be her sissy then hitched up her skirt and ordered l was to take down her knickers and clean her sticky hole as Graham a young doctor at the hospital had given her a good fucking in the back of his car before she came home.
Getting to my knees in front of her, l took hold of her knicker waist band and eased then down to her ankles then off, Jolie told me to lick the crutch, l held her knickers to my face and could smell the strong odour of seaman, “lick it” she screeched, l poked out my tongue and slid the crutch of her knickers down my tongue. The seaman taste sent a tingling through my whole body l felt my own watery spunk dribbling down my inner thigh, Jolie spread her legs and ordered l clean her, l got straight on with the job, burying my tongue between her sticky pussy lips, Jolie’s clitty started to swell, so l began sucking her clitty hard she yelled “don’t fucking stop, don’t you fucking dare” and pushed on the back of my head hard into her moist sticky pussy.
I gently bit on her clit this caused Jolie to cry out calling me a dirty whore, she thrust herself against my mouth and squirted, she had such a tight hold on my head l couldn’t move her gush squirted into my mouth, “drink me sissy, swallow it all” Jolie hissed.
Once she recovered from her orgasm Jolie got to her feet and said she was going for a bath and l was to clean up the wet patch on the sofa cushion and carpet because she was bringing a friend home the following evening and didn’t want the room smelling, before going for her bath Jolie informed me we were going shopping in the morning as she wasn’t sharing her clothes with a dirty little sissy, and left the room.
The next day we had breakfast then left for the shops l felt sick the closer we got to the shopping centre, my wife parked l got out the car and froze, she cruelly told me there was no point in hiding l had to go out sometime then announced that’s she couldn’t call me little sissy when we were out and asked if l liked the names Cloe, Rose or Cindy, l replied Cloe sounded nice Jolie nodded and said we were going to get me underwear first then scout a few charity shops for dresses, skirts and tops she turned and walked towards the centre as l followed l could feel the eyes burning into me.
Getting my underwear didn’t take long as my wife brought me plain simple bras and smart cotton knickers which l called Bridget Jones knickers, she gave me a glare and whispered “my sissy will wear what l say” then gave me a false smile before saying, Cloe l bet you can’t wait to get home and try your new undies on, well Jolie was half right l couldn’t wait to get home. She must have dragged me into every charity shop to buy all the old-fashioned clothes she could find, in one of the charity shops Jolie brought me a ginger wig to finish off my wardrobe then thankfully we went home.
When we got home, Jolie told me to change out of her clothes and warned me never wear her clothes again. I went to my room and redressed the bra l padded with loo roll and my knickers were a bit tight the white blouse and blue skirt fitted well, l looked at myself in the wardrobe mirror and fixed the ginger wig then l ventured downstairs dressed as my wife’s sissy Cloe.
Jolie was sat at the kitchen table, she told me to turn around for an inspection and explained the person coming for a drink was Martin the bloke we first met dogging. They had been meeting after work so he could fuck her, Jolie justified their fucking behind my back as my fault due to me having a tiny cock and not being able to produce a healthy load of cum.
Before Jolie’s guest arrived she put makeup on me then l had my orders for the evening which were basically l could be seen, but not heard. Jolie had drank almost a bottle of wine when the door-bell rang, so l went to let Martin in. I had forgotten how he was over 6ft with broad shouldered and l have to admit me being 5ft-6 with a slim frame l felt small standing in front of him. I showed Martin into the lounge and he commented on my dress, Jolie told him l was her sissy and she had named me Chloe, then added to be a man you need a cock and spunk filled balls and this sissy has neither, the pair laughed.
It wasn’t long before they were taking each other’s clothes off, l was sat in the corner every so often Jolie would meet my eye and make a sarcastic comment when wanking Martin by telling me it is a shame l never had a real cock like Martin’s then sucked his balls and with her mouthful Jolie would tell me how she couldn’t wait to get his steaming hot creamy spunk inside her.
They were both naked on the floor, Martin was propped up against the sofa and Jolie had her head between his legs wanking and sucking his cock, l could hear the slurping and sucking sound she was making. Martin had his head tilted back sighing and groaning as my wife worked on his hard shaft, l have to say l was beginning to find watching them was turning me on then Martin shouted “l’m cuming” and pushed my wife’s head downward so she had no option but to take his hot creamy sticky load straight down her throat, l also felt a warm dampness in the crutch of my knickers, it was my own tiny amount of cum there wasn’t enough to keep my wife or any woman happy, but l felt quite proud at shooting something.
After Martin shot his load down my wife’s throat she lay between his legs her hand firmly gripping his shaft to slowly wank him, Martin looked over at me then bushed his hand through Jolie’s hair and told her to work on his cock because he was going to give her a good fucking since her sissy husband couldn’t, Jolie took a sip of wine then l watch her lower her head and swallow up Martin’s shaft into her open mouth.
He put a hand either side of Jolie’s head and began slamming it downwards onto his cock then placed a hand onto her bum and rammed a finger into her arse hole, Jolie gave-out a little cry and worked her mouth faster on Martin’s shaft. He must have been near to emptying his balls once more because he yanked Jolie’s head up and she lay on her back with legs spread wide, Martin got into position between her legs clutching his hard cock and fed the whole shaft fully inside my wife’s eagerly waiting pussy. As they fucked each other all l could hear was their grunting and heavy breathing every so often Jolie would yell “harder baby, harder!”, Martin just let out “ugh, ugh yeses” as he rammed his thick rock-hard shaft deep into my wife’s hole.
Jolie was panting which got louder and louder, she was starting her orgasm; l knew this sound from when l’ve had to lay next to her in bed while she fucked herself with a rabbit.
From where l was sitting l got a good view of Martin’s thick shaft sliding in and out of my wife like a mechanical piston which all of a sudden increased it’s speed then her pussy swallowed the whole length and Martin yelled “oh baby, l’m gonna flood your tubes” and held his shaft firmly inserted between Jolie’s pussy lips filling her with his sticky love liquid, she dug her nails into his back leaving scratches like whip marks. Their panting and groaning subsided and they lay joined together in a sweaty heap, after a long kiss Martin lifted himself from between my wife’s legs and sat against the sofa the head of his cock had a covering of spunk.
Jolie lay on her back with her legs still spread, she half sat up and ordered l make myself useful and clean her dribbling sticky pussy, Martin had indeed filled my wife with a very full thick load, Jolie pulled my head into her hole and as l thirsted on Martin’s spunk she told me that Martin was now the man of the house, l finished cleaning my wife’s pussy and about to return to my seat when Jolie ordered that her lover would like to be cleaned and gave a little laugh, Martin held his cock and rolled his foreskin down. I crawled between his legs gripped his shaft and began licking his urethral opening, Jolie pushed the back of my head forcing Martin’s cock down my throat, “suck it!” she demanded. His cock tasted very salty, l found myself enjoying the flavour and the smoothness on my tongue, my wife ripped my head up and told me to go sit down.
They fucked each other another 4 time with me cleaning them both afterwards, l thought Martin might have stayed the night, but he had to get home to his wife. It was nearly midnight when he left in a taxi, my wife Jolie went to her room and l went to mine.
When l got up the next morning Jolie had gone to work there was a shopping list on the table, l told myself l had to go out sometime on my own and it wasn’t a big list so l could get what we needed at the minimart two roads away.
About 10am Alice knocked at the door as soon as l saw it was her l was about to apologise for the kiss we had, but she stopped me and explained why she dashed off, it was because Alice enjoyed us kissing, but felt guilty as she had only ever kissed her husband in such a sexual way. What she said sent cross messages to me, did Alice mean she wanted us to go further or just forget what happened, anyway for now l was happy she was still talking to me and we sat down to have a coffee. I was telling her that my wife Jolie had left me a shopping list,, but was nervus to go out, so Alice said she will come with me which was a great relief to hear.
The shopping trip with Alice wasn’t so bad as l imagined and we were really getting on, she kept reminding me to walk like a woman, when we returned Alice invited me into her house for a coffee, but that was replaced with a glass of wine.
Our conversation got around to my wife Jolie and what she thought of me as a woman, l don’t know why but l began telling Alice about Martin and Jolie, Alice put her hand on my knee and said she thought l looked wonderful then asked me to kiss her, her lips met mine our tongues entwined and we both sank back in the sofa.
I got my hand under her skirt and into Alice’s knickers, her pussy was very bushy, l whispered “l want to eat you”, she answered by opening her legs which spread her 60-year-old pussy lips, Alice’s clitoris had swollen and protruding from between her lips l gently rubbed my thumb over her clit she let out a gasp. I lowering myself into position and peeled down her knickers, put my mouth over Alice’s clit and started sucking her, she was pushing her crutch against my mouth whimpering, her love juices began to low like a babbling brook Alice was soaking me.
We moved to the floor l raised her legs and really wet to work on her pussy, she wriggled and squealed, l removed my knickers and we got into a scissor position the feeling was fantastic l rubbed my small dried-up wrinkled scrotum hard against Alice’s dribbling pussy even l started groaning, she began shacking and shrieked “oh yeses” then lay on the floor panting. When Alice caught her breath, she exhaled and confessed that was the first orgasm she had ever had as sex with her husband was once a month and anniversaries, it had been this way since they got married 42 years ago. That afternoon we taught each other many things and l don’t think Alice nor l had ever had such a wonderful few hours.
I had been dressing as a woman for 5 months, l didn’t need to wear wigs as my hair had grown and Alice’s training had helped me look more passable as a woman, my wife was bringing home different men, but Martin was her most regular.
One lunchtime Martin knocked at the door l explained my wife Jolie wasn’t home, but he still wanted to come in, so we went into the kitchen and l started to make us a drink when Martin grabbed me from behind turned me around and kissed me, l was powerless to do anything he was much stronger than me, Martin was over 6ft and broad shouldered compared to me at 5ft-6 with a thin frame. Next l was leant over the table and held in place by his large hand at the back of my neck, my skirt was wrenched up and my knickers ripped off, Martin declared he had never fucked a sissy.
I felt the warm head of his cock passing between my bum cheeks then my arse hole being stretched by the head of Martin’s cock, slowly his shaft sank further inside me the pain wasn’t unbearable, but extremely uncomfortable, my god Martin did have a thick hard cock.
When his hard rod was fully inside me he took hold of my hips, “ready sissy bitch” he asked and began fucking me hard and fast, l don’t know what happened, but the thrill of being fucked began to get me very aroused and l found myself pushing backwards to meet Martin’s forward thrusts. He must have been near to emptying his sticky load, l swear the head of his cock inflated just before he yelled “oh fuck yeah” and gave one hell of a thrust into my arse. I screamed with excitement as l felt Martin’s creamy hot stream of spunk flow from his urethral opening, once he delivered the payload he began giving little jerks into my hole then before sliding his cock from me Martin remarked “you’re nice and tight”, he slapped my bum and dressed where as l lay across the table well and truly fucked with a creampied arse hole, but l felt bloody good, it was about 20 minutes before l went to clean myself. I didn’t feel my wife Jolie needed to know about my visit from her lover as l knew Martin was going to make many more quick visits.
My wife Jolie came home and announced she was taking me to an Ipswich hospital to see a cosmetic surgeon, she wanted me to have breast implants and to get something done with my dried-up shrunken scrotum between my legs, it was made clear l didn’t have a say in the matter, but l didn’t really mind because l was enjoying my new life as my wife’s sissy.
It was a quiet drive to the hospital and the surgeon was a nice woman l didn’t do much talking as my wife basically told the doctor she wanted me to have breast and my balls removed. I was stripped and examined it was then the doctor declared she couldn’t give me the cut as my cock was to small so couldn’t insert it inside me to make a vagina, but she could shape my scrotum to look like vagina lips, but before any implants and operation l was put on hormone treatment.
I shall write how my hormone treatment went and what happened on the return visit to the Ipswich hospital.
Yvette
- 02.03.2021
- 37
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