I’m Ed’s Cross-dressing Home Help. free porn video

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I had been made redundant and the employment for the area wasn’t great, l was in town with my wife and in an age-help charity shop was a card asking for volunteers and my wife suggested l apply as it will keep me doing something while l look for a proper job. I went inside to put my name down and by the time l got home there was a message from the shop asking me to come in for a chat.
I went in the next morning expecting to be interview for work in the shop, but the volunteers they were looking for were for people to help in the old persons home, l explain l had no experience, but the woman and man interviewing me said l didn’t need any training as l would simply be washing up or hoovering, but would be police checked which l didn’t mind, the interview ended and l went home to wait.

I didn’t hear anything for about 3 weeks then got a call from the woman who interviewed me to say there was a gentleman who needed help at home and would l like to meet him that afternoon, l said “yes” and she gave me his address.
The house was all alone in the country and quite large, the woman was already there when l arrived and we went inside. She made some tea while l chatted to the old man, he introduced himself as Edward, but his friends call him Ed. He was in his late 70s and looked quite sprightly for his age and we got on, before leaving it was arranged l start my volunteering the very next day at 9.30am.

When l arrived at Ed’s my first job was a bit of hoovering then filled the dishwasher as that cleaned Ed and l had a tea break, he did most of the chatting, the rest of the time was spent doing light work then l left.
By the 7th visit to Ed’s things were very relaxed between us, he would joke and ask if l have brought a nice woman for him today. I was in the kitchen when Ed wondered in and said his carer had let him down which meant he wouldn’t be having a shower again, he seemed really pissed off, so l offered to help him into the shower and he could call me when he finished, Ed jumped at the offer and we went up to the bathroom.
I helped him to undress to his pants and left him to shower while l got on with making the bed, l thought l heard Ed call me and went into the bathroom he asked if l could sponge his back, l didn’t feel embarrassed, l grabbed the sponge and began washing him. When that was done Ed turned around and from under his round belly was the longest erect cock, he raised his arms and said “now the front”, it didn’t feel awkward till l got to his round belly which he lifted with one hand then took hold of his shaft with the other hand and started wanking himself, l was mesmerised by Ed’s swollen mauve cock head, he said he wouldn’t mind if l wanked him at the same time as l washed his erection, Without thinking l rubbed soap into my hands and gently gripped his shaft and began sliding my hand up and down, Ed began sighing and letting out low whimpers then without any warning a little stream of watery spunk flowed from his urethral opening and down my hand then was washed away by the shower, he thanked me and l dried him off, Ed walked into his bedroom naked to get dressed while l made his bed. We went down stairs and before l left we sat chatting, Ed was hinting at getting wanked off on a regular basis’s, l joked how many showers does he have a day. On the way home l found an envelope in my pocket with money in and a note asking how much do l cost.
The next time l went to Ed’s l had to let myself in because he had fallen asleep in front of the telly with his robe open, but what got my attention was the porno film on the telly. I didn’t wake him, but got on with emptying the dishwasher and rinsing a few cups, l didn’t hear Ed come up behind me till l felt his arms around my waist he whispered “how much do you cost”, l had never been with another man before, but l was feeling aroused, my love life at home dried up years ago and may be it could be relief sex for me having a bit of fun with Ed, so answered what you looking for, Ed said softly “come to my room” then left the kitchen.
I stood in the kitchen trembling, l could have walked out the door, but instead l walked upstairs and poked my head around Ed’s bedroom door, he was sat naked, he saw me and beckoned me in.
I stood in front of him, Ed got to his feet and peeled my T-shirt over my head, he put his arms around me then pulled me close l could feel his hairy chest and erect nipples pressing against me, he took my hand and placed it onto his cock which l gently squeezed , Ed gave a sigh and pressed his lips to mine his tongue forced its way into my mouth our tongues entwined and l closed my eyes, at that point l found myself getting so excited, l didn’t know what to do or what Ed had planned for me, but my cock was bursting to get out.

My trousers were being unbuckled, Ed lay me on the bed and pulled my trousers and pants completely off, he faced me on my belly and lay on my back his long hard shaft sat between my bum cheeks. He was kissing my neck telling me how l was going to enjoy myself, next Ed began sliding himself up and down as if to be fucking me, his weight was causing my cock to also slide up and down on the sheet under me.
The faster Ed rubbed his cock up and down between my bum cheeks the more excited and harder my cock became and l knew it wasn’t going to be long before l shot my spunk into the sheet, but Ed yelled “here l go”, l felt his warm creamy liquid oozing between my bum cheeks. We lay on our sides Ed gripped my cock and started to wank me which he didn’t have to do for too long, l shot my load over his hand and sheet.
Ed turned me on to my back and kissed me then said he wanted to show me something, we went into another bedroom and he opened a wardrobe full of woman’s clothes then a chest of draws filled with woman’s underwear, Ed opened a jewellery box containing clip on ear-rings, necklaces, dress rings and then informed me it was his sisters room, but now he would like me to use it, he wanted me to dress in his sisters clothes when l came to his house and as he put it, for when we have our fun.
Ed suggested we turn the bedroom into our fun room which sounded good to me, l was nervous, l was hesitant and scared, but l was also very excited, he slapped my bum took my hand and led me back into his bedroom.
I was laid face down on the bed, Ed ran his fingers up and down my spine sending a tingling throughout my body, he said softly “please suck me”, l rolled onto my side and Ed stretched out on the bed his cock standing upright. I took hold of his cock and slid my hand down to the base the purple head glistened and my mouth was instinctively drawn to the bulbous shape, l closed my lips around Ed’s hard shaft and could clearly taste his pre-cum on my tongue with a salty flavouring from when he shot his creamy load earlier. He held the back of my head to encourage me to slide my mouth up and down his long stiff shaft the excitement was building in me, Ed was raising his hips to meet my downward motions, he gave a gasp lifted his hips, “l’m cumin, drink” he murmured. I felt a warm liquid shoot from Ed’s open urethral there wasn’t a lot and l swallowed his full load then gave his cock some gentle sucking while he lay sighing. When l couldn’t get any more cum out of him, he pushed my head downwards, so l started licking and sucking his saggy balls, Ed’s sighs got louder we stay on the bed for some time till we were both exhausted.
When l did finely get from the bed to finish the cleaning Ed asked if l could do it naked the cleaning didn’t take long and before leaving we had a hot drink, yes l did dress to go home and like before there was an envelope in my pocket.

On my next visit to Ed’s he had brought pink paint for our fun room with matching pink quilt cover and pillow cases there were brushes and rollers on the bed, he had also ordered a dark pink carpet which was due the following day, Ed declared he wanted me to have a girls room if l was going to be his girl then suggested l paint in knickers and a bra which l was more than happy to do, so l stripped and got quite excited when l slid the knickers up my legs, they were a little tight, but held my cock comfortably. The bra l had to fill with padding, l could see Ed liked what he saw as he was now naked and wanking his stiff cock, l opened a tin of paint to start the decorating, but Ed stopped me and said “be a good girl”, l knew what he wanted so knelt in front of him and took his cock into my mouth.
I took his shaft between my lips, he held the back of my head and began fucking my mouth, Ed’s cock head reached the back of my throat, l tried my hardest not to choke but l was having trouble because Ed was really ramming his cock hard into my mouth, l was about to pull my head back when he let out “swallow, swallow every drop”, l didn’t have much choice because his warm salty liquid dribble down my throat into my stomach, but l would have happily drank all Ed shot.

Once he had emptied his creamy load Ed left me to get on with the decorating dressed in his sisters knickers and bra, in just over two hours l had painted the room also put the quilt and pillows on the bed, once the pink carpet goes down no one could say it wasn’t a girls room, my room.
While l was alone in the room l took the opportunity to go through one of the wardrobes and found some quite sexy outfits that l couldn’t wait to try on and best of all there were four wigs of different colours and styles, l was very tempted to try a few dresses and a wig on to surprise Ed, but through rushing to paint l had pink dots all over me, so went for a shower.
I turned the shower on and before l had removed my knickers and bra Ed appeared smiling in the doorway, l was about to strip when he asked me to stand under the cascading water in the knickers and bra. I did as l was asked, Ed began stripping then joined me under the shower, he lathered my whole body and told me to put my hands on the wall, he put a hand around me and slid it into my knickers to grip my cock, l let out a gasp his hard shaft pressed against my bum cheeks the crutch of the knickers l was wearing was pulled to one side.
My heart was pounding and my breathing turned to pants as the head of Ed’s cock slid between my bum cheeks he softly asked me to push my peach shaped bum out, l knew what was going to happen l had been expecting it to happen. The bulbous head of his cock began to part my hole which l did find uncomfortable, Ed must have been almost fully inside me when he whispered “your man pussy is perfect”, he pushed the full length of his slim hard cock up inside me, “l’m gonna get you pregnant” he declared. He eased his shaft part way out of my arse hole then thrust it back inside me, Ed was holding my cock so as he fucked me it felt like he was also wanking me the speed he was fucking me got faster, l could hear him mumbling “is that good Kathy, is it good”, l didn’t say anything, he and l were enjoying the fuck in the shower.

I knew Ed was close to shooting his load as the head of his cock really did balloon and l could feel that even more because his shaft was firmly inserted up inside my man pussy as he called it. He gripped me tight and opened the gates to his balls, gush after gush shot from the end of his cock filling my rear, l played along with him getting me pregnant and said “l’m going to need bigger dresses when l get pregnant”, Ed’s cock slowly slid from my man pussy followed by a little trickle of his spunk which was washed away by the water.
I finished washing the paint off while Ed dried himself, it was then l asked who is Kathy, he explained she was his sister and confessed she was also his lover, he always wanted to get her pregnant, but it just didn’t happen. So, l asked if he wanted me to pretend getting pregnant as l could put a pillow under a dress, Ed immediately replied “yes” then declared he is going to enjoy getting me pregnant and from then on our role play started he was the husband and l was his wife who he was going to get pregnant.

The next time l went to Ed’s we didn’t have time for any fun as he had forgotten about a hospital appointment, but before going he said it was his birthday the coming Thursday and was having 2 or 3 friends around for a drink, adding he would like me to be the hostess and without thinking l replied “l would love to”, then as Ed went out the door he told me to have a look at our fun room, so l did the tidying as quickly as l could then went into my pink fuck bedroom. The deep shagpile carpet was down and looked great, he had hung pictures of naked pregnant woman being fucked on one wall and the other were large naked woman in sexual poses and just above the headboard hung a large close up of a cock wedged firmly into a dripping pussy.
I took my shoes and socks off and walked over to the chest of draws and began sorting out something to wear for Ed’s birthday party then it hit me, l was going to be dressed as his wife and his friends were going to be there, a feeling of apprehension mixed with excitement stirred inside me and excitement won the day, l carried on looking through the draws and found a girdle that had suspenders attached, in another drawer there were black stockings and all the knickers were the high sensible type, but l managed to find a thin black pair, next l looked through one of the wardrobes and picked out a black dress with a little split at the back which l was tempted to make higher, all l had to decide on now was which colour and style of wig to wear.
Then as l was leaving the room l realised that l hadn’t picked out what jewellery l was going to wear for Ed’s birthday as he would want me to look my best in front of his friends. The jewellery box played a tune when l opened the lid, l picked out a heart pendent neckless and dangling clip on earrings then tried two large dress-rings which fitted my little fingers, l laid everything onto the bed then went downstairs and before leaving l left Ed a note telling him l need lipstick and eye makeup, ending the note with ‘looking forward to your birthday’.

I informed my wife l may be late Thursday or not home at all because Ed had invited me and a few friends for a birthday drink, of course l left out l would be the hostess. Thursday came and l left for Ed’s, l was so excited, l couldn’t wait to try on the clothes l had picked out and have Ed introduce me to his friends, l wondered what they might say or how they would treat me. Arriving at Ed’s l noticed there were no other cars parked outside, l knocked on the door it swung open and l went inside, Ed asked me to hurry and change because his friends would be arriving soon and he wanted me to answer the door to them, l told Ed he was to wait down stairs and l will come down when l had changed. Rushing to my pink fuck room l quickly stripped and put on the stockings then the girdle, next padded out my tits and stepped into the black dress, l had a bit of trouble zipping the back.
I looked into the large wall mirror and fitted the auburn bob wig, l saw Ed had got the lipstick, it was a blood dark red l ran the lipstick around my lips and applied the eye makeup, next came the heart neckless and earrings then last of all l slid the dress-rings onto my little fingers. I looked in the mirror and turned one way then the other, took a deep breath and went downstairs.

Ed met me in the hallway, l asked if l looked alright he didn’t answer just pulled me to him and we kissed, our tongues deep in each other’s mouths, we were interrupted by the door-bell chime sounding, Ed released me to answer the door l was nervous as hell and took a deep breath before opening the door. On the doorstep were three gentleman all about the same age as Ed, l asked them in and as they passed me each one kissed me on the cheek except one called Richard he had a grope of my bum and remarked “nice and firm” this made me feel more relaxed.
Once they were all in the lounge l took in the drinks glasses and Ed introduced me by telling everyone he was breeding with me then introduced his friends, Richard, Cyril and Norman who was the designated driver so couldn’t drink, l said it was nice to meet them then told Ed l had a few bits to do around the house then l’ll join them, he slapped my bum, l left them to reminisce and drink.
I was in the dining room when Norman came in and asked for a cup of tea, he stood very close and had a cheeky grin he stated that Ed had told him all about me, it was wrong of me but l flirted with him even letting Norman kiss me which turned into a full blown deep French kiss, l put a hand onto his groin and had a hard thick cock pressing against my palm. Norman put a hand under my skirt, “wow stockings” he gasped, l stopped him there and said l’ll bring his tea into him, but he wanted more asking me for a quickie, l giggled and told him he was a naughty man and went into the kitchen to make the tea and Norman went back into the lounge.

I made Norman his tea and took it into him then sat next to Ed making sure that Norman and Cyril who were sat opposite me got a good view up my dress. Ed poured me a drink and after two hours of drinking everyone was quite merry and l was receiving sexual comments from all the men and loving it. A song came on the radio and Ed asked me to dance as we swayed around the room we began kissing and he began fondling my bum which came to a stop when Cyril cut in and ask Ed if he could taste his breeding mare, Ed replied “by all means”, Cyril pressed his lips to mine we French kissed as the other’s watched on, then Cyril took my hand and placed it on his groin his cock was hard, but not as large or thick as Ed or Norman’s.
As l kissed Cyril the other men and Ed began chanting “take the dress off, off, off”, l turned around and let Cyril unzip my dress which fell to the floor, l got wolf whistles. Which seem to encourage me to do something, so l got to my knees in front of Cyril and took out his cock then gave his stiff shaft a few slow wanks before taking him into my mouth, he gasped and pushed his cook to the back of my throat. I couldn’t quite get his shaft into my throat but he was enjoying the sucking l was giving him, Cyril’s whimpers got louder when l gently squeezed his balls then he let out a cry “l’m cuming”, l kept my lips tight around his shaft so as not to waste any of his sweet tasting steaming hot load as Cyril shot the last of his spunk l thought he was going to keel over, but he made it back to the armchair looking exhausted.
They hadn’t finished with me yet Robert got to his feet and helped me up then told me to lose my knickers which l stepped out of he then put me on all fours on the sofa took his hard-throbbing cock out and eased it’s purple shiny head between my bum cheeks straight into my waiting arse hole. I have to admit Robert’s shaft was more comfortable than Ed’s, l wiggled my bum, he took hold of my hips and started fucking me, the rest of the men were cheering and egging him on to fuck me faster. Robert was really ramming his shaft home into me the sensation was driving me wild, “you need a good fucking, don’t you” he growled, my reply was “give it to me baby” and Robert was doing just as l asked, he yelled loudly “l’m cuming!” pulled me onto his shaft and began delivering his payload deep into my rear, l was panting heavily catching my breath. Once he emptied his ball sack, Robert slid his shaft from me and congratulated Ed for having such a good breeding mare, l didn’t get chance to move as Norman was now behind me with his cock in hand ready to take his turn with me.
I felt Norman sliding up inside me, l would say he was the same size as Ed, but more rough, Norman had a very tight grip of me and fucked me hard, as he did he was calling me an old man’s spunk dump. He kept up a really fast rhythm which began to give me a stiff cock the other men were encouraging him to shoot his load, but Norman just carried on fucking me deep and hard, Ed stood in front of me and stuffed his cock into my mouth, held the back of my head and began fucking my throat.
All of a sudden l had an earth-shattering climax my whole body convulsed as the two men spit-roasted me and as l slowly came out of my exploding climax, Norman let out a gasp and began filling my rear with quite a full hot creamy load of his spunk, Ed pulled my head onto his cock and yelled “l’m coming baby, l’m cuming”, l felt his hot sticky cum sliding down my throat, l managed to gulp sending the load straight into my stomach as Ed slid his pre-stiff cock from my throat l got the distinct taste of his salty spunk on my tongue.

Norman wiped his spunk dripping cock over my bum and l didn’t waste a single drop of Ed’s load he got a good sucking, when they put their cocks away l got from the sofa and a gush of spunk flowed from my male pussy and ran down my legs even my own cock dribbled with cum. Ed beckoned me and asked for a kiss then after our hard French kiss he remarked l’d better take a shower and a change of clothes.
I was in the shower when Cyril came into the bathroom turned off the shower then ordered me to my knees, took out his cock and started peeing over me, when he finished l re-showered and went to my pink fuck bedroom and picked out another set of clothes, but l wanted to look different, so dressed in just bra and knickers with a see through silky slip and this time wore the long haired dark wig, replenished my lipstick and went back to the lounge.
The men were now quite drunk except for Norman who was the designated driver l did try wanking Ed, Cyril and Richard but gave up, so me and Norman left the other’s to carry on drinking while l took him to my pink fuck bedroom.

Norman and l lay on the bed kissing, his cock had recovered from earlier so l began wanking him, he asked if l would consider coming to his house to clean then winked and offered me benefits of £20 an hour, but he wanted me to dress as a nurse, he will supply the uniform.
I didn’t have to think for long and said “yes”, but emphasized l would still be looking after Ed as well, Norman agreed. We got into a 69, l was forcing my mouth down onto his shaft taking Norman deep into my throat the crutch of my knickers were being pulled to one side, l felt a warm wet feeling around my cock and Norman flicked the tip of his tongue over my urethral opening. I was then rolled onto my back Norman lifted my legs and took position then slid his hard cock into my man pussy right up to his balls there was no slow start he was ramming his shaft in and out calling me a two-timing bitch because l was Ed’s fuck mare.
What with Norman groaning and me panting we were quite loud fucking then he let out “oh yes, yes!”, l felt his cock pulsating then the hot liquid began oozing from his cock head filling my rear, when l was full Norman slid his shaft from me, l rolled onto my side and he slapped my bum telling me he will give Ed his address and hopes to see me soon then left to get drunk Robert and Cyril home.

I didn’t go down stairs, but waited for Ed to come to bed, he wasn’t in a fit state to do anything as l did try giving him a good suck, so l surprised him in the morning by putting a pillow up my slip to look pregnant then when he noticed my bump l confessed l didn’t know if he got me pregnant or it was one of his friends it was then Ed came to life l was put on all fours and fucked hard, l don’t know what it was, but he really gave my man pussy a full sticky load much more than normal.

The following week l started cleaning Norman’s house dressed as a nurse and it turned out there was a reason he wanted me in a nurse uniform and once Robert and Cyril found out how good l can clean and take care of Norman and Ed’s needs they too wanted me to visit them, my volunteering turned into a full-time job that paid a good wage with great benefits and fun.

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Im Eds crossdressing home help

I went in the next morning expecting to be interview for work in the shop, but the volunteers they were looking for were for people to help in the old persons home, l explain l had no experience, but the woman and man interviewing me said l didn’t need any training as l would simply be washing up or hoovering, but would be police checked which l didn’t mind, the interview ended and l went home to wait. I didn’t hear anything for about 3 weeks then got a call from the woman who interviewed...

1 year ago
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Dogging Cross Dressing and Porno

This new friendship proved to be fun and fulfilling, the girlfriend and the wife quickly became best buddies and the location of our nights together changed to her house. If we had nothing organised and they were free we spend Fridays or Saturday evenings in each other company. Usually just talking and drinking but more often than not some form of sexual encounter. Even vanilla fucking was done in each other company and the girls enjoyed playing with each other exploring the lesbian side of...

1 year ago
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Old lady fucks her cross dressing friend

Hazel was fed up using her fingers and dildos and fed up of being one of the invisible elderly generation. She wanted more – a lot more – sex, so she decided to expand her sexual horizons. To ensure that she put an advertisement on the web. "Larger mature lady, single, (70), open minded seeks new experiences, fun and frolics. I am 5’ 4”, dress size 18 with 36D bust and welcome either gender and any age.She was amazed that it attracted a few older cross-dressing men, which surprised her greatly...

4 years ago
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Old lady fucks her cross dressing friend

Hazel was fed up using her fingers and dildos and fed up of being one of the invisible elderly generation. She wanted more – a lot more – sex, so she decided to expand her sexual horizons. To ensure that she put an advertisement on the web. "Larger mature lady, single, (70), open minded seeks new experiences, fun and frolics. I am 5’ 4”, dress size 18 with 36D bust and welcome either gender and any age.She was amazed that it attracted a few older cross-dressing men, which surprised her greatly...

4 years ago
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  • 28
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Old lady fucks her cross dressing friend

Hazel was fed up using her fingers and dildos and fed up of being one of the invisible elderly generation. She wanted more – a lot more – sex, so she decided to expand her sexual horizons. To ensure that she put an advertisement on the web. "Larger mature lady, single, (70), open minded seeks new experiences, fun and frolics. I am 5’ 4”, dress size 18 with 36D bust and welcome either gender and any age.She was amazed that it attracted a few older cross-dressing men, which surprised her greatly...

3 years ago
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Bi MMF FemDom Cross Dressing Cuckold Part 1

I have these friends, a husband and wife. For the longest time, I've wanted badly to have sex with both of them. First I wanted just him, but I thought it would be even better if I involved both of them.I'm bi, but they don't know that. Anyway, after years of hanging out with them, I see how domineering she is over her husband - my friend. She really puts him down, bitches at him constantly and belittles him, in front of anybody and everybody. She's really mean, but she's mostly been nice to...

2 years ago
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My CrossDressing for a couple fantasy

For some reason just recently i have found myself having a recurring fantasy of wanting to try cross dressing for a bi-sexual couple. Several years ago i did try cross dressing just the one time for a dominant top guy but since then have never really given it any more thought, besides i personally have always seen myself as dominant rather than submissive, but having watch a few sissy porn vids and various CD clips i have found myself increasingly turned on at the thought of giving it another...

2 years ago
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It Starts Again A Cross Dressing Fantasy Chapter

Have you ever been transported through time in an instant? I know, not possible, but that is what it felt like as I finished reading the note pinned to the bra Beth had left in my dresser drawer. Imagine that you were a 13 year old guy and you suddenly found yourself drawn to wearing women’s undergarments. And now those long lost urges were flooding back into your brain.I can tell you exactly when this all began for me. It was in April the year I turned 13. My mother was busy at the kitchen...

2 years ago
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Cross Dressing play turned horribly wrong fantas

It was just another warm Sunny weekday morning like any other in summer. My wife kissed me goodbye as she left for work, I took my usual pervy glance at her as she wiggled her hot behind out the door, I was setting up in my home office, ready for another day of working from home. I listened to the car roll out the driveway then the gate closed, I started working through the usual emails and meeting requests.. I got bored of work after a couple of hours I decided to go into our bedroom and rifle...

4 years ago
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Cross dressing for my boyfriend

My name is Chris and I’m a 25 year old, white, bisexual male. I stand 5’9″ and weigh 135 pounds with light brown hair and brown eyes. I’ve always had somewhat of a feminine body and I’ve always enjoyed being a “bottom” when with other men. I met my boyfriend Mark about a year ago at a bar. The minute that I saw him, I knew I had to have his cock inside of me. Mark is 27 years old, 6’2″ and weighs 195 lbs with brown hair and a very hot body. He works out a lot and plays some sports. You could...

Lesbian
4 years ago
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It Starts Again A Cross Dressing Fantasy

It had been a particularly hard week at work and was so happy to pull into the garage and put the door down. I sat a moment looking at the empty space in our double garage wondering why Beth was not home, and the remembered that she said she was working until 8:00 PM tonight.I walked into the house, kicked my boots off, dropped my lunch box by the sink, and stripped my shirt off as I headed to the bathroom to get a much needed shower. Our laundry closet door was open so I deposited my work...

4 years ago
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Cross Dressing to go to Girls School

As a boy I was slim and in some ways feminine looking. For example it used to annoy me when I went into a shop with the hood of my coat up because of the weather to be addressed as “hen” rather than “son” – these being terms used in the Glasgow area back then. I went to a co-educational school and had a great time with the girls I met there, all the way from my first day in “primary one” to the sixth form. I did have a fling with one of the PE teachers there brought on by too much to drink...

7 days ago
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Cross dressing and letting her fuck me with a strap on

Crossdressing is often looked down upon and it is often greeted with a frown. However, being a crossdresser, I would say that it is a thrilling ride. I was bullied all through my adolescence for being ‘feminine’ and when I came out as bisexual, I faced innumerable backlashes and was subjected to humiliation. However, I was lucky enough to have a handful of friends by my side, whom I could not thank enough. I was raised by a single mother after I lost my father to a brain stroke when I was at a...

Cross Dresser
4 years ago
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My first black cock as a cross dressing schoolgirl

It’s 1995, and I’m in year 9 at school. I’m been cross dressing for longer than I care to remember. I’m fascinated by tights, and I’m fortunate to be at school in the era of the Spice Girls and Girl Power. Skirts are as short as possible, and everyone is wearing platform shoes. I’m in my element. I’ve recently discovered my best mate also cross dresses, but he’s lucky in having a slightly younger sister who has a very nice wardrobe to raid. I’ve also discovered he’s a very heavy cummer, and...

3 years ago
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Wanted A Horny Crossdressing male

Information: This story is set out as an ad in a porno magazine but it is entirely a work of Fiction I invented. It should be taken of somewhat as a joke. Wanted: A Horny Cross-Dressing Male Hi I'm Foxy Roxy, you may have seen me in action in one of the many porn flicks I've been in, but if you haven't, here goes. I am a thirty-six year old married woman with big tits and blonde hair. I like to wear a leopard print crop top and matching pants. I'm always horny and up for...

4 years ago
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Cross Dressing Pegging and the Promise of a Three

After my last session with Ann, the gorgeous older woman (we’d call her a MILF nowadays) who’d discovered my love for cross-dressing, things were quiet for a couple of weeks. She’d only ask me to visit her when she knew her husband and son would not interrupt which so far meant when they had gone off to watch their football team playing away. It seems that they had a run of home games.Mind you, keen as I was to play with Ann again I did also enjoy replaying our sessions whilst lying on my bed,...

3 years ago
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Consequences of Cross Dressing 2 FIN

Tony's Companion All week I tried to come up with ways of getting out of this date with Tony. I cried, begged, and pleaded with Grace to come up with another date for Tony, and to convince him to let me out of being his date to the Charity Ball. She would have no part of it and engaged my mother to take me shopping for an evening gown suitable for the event, and something to compliment Tony who will be in a tuxedo. "Amy, you have to stop begging. Tony is excited about Friday and...

3 years ago
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Me My Uncle And Cross Dressing

This is my story. The story about my introduction to the sex world. Hello guys i m Ankit from Hisar, Haryana. This story is from my past or i should say this a biography. It was all happened when i was in 12th class. But i m telling it in present tense. I am slim and cute. We are 4 members in our family. My parents, my older sister and me. We are living at the end of the city in. My uncle lives next to our house. He live alone. He is retired from his job and living a luxurious life. He is very...

Gay Male
2 years ago
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Cross Dressing

It was the early 80's and I was over my friends house who's dad had a ton of porno mags in his laundry hamper in his bathroom. We used to look at it while his mom and dad were at work. We loved the looking at the hot girls but what got me the hottest were the guys who dressed as girls. When we couldn't take it anymore we would jerk each other off but I was the only one willing to give head. At 18 years old these guys would explode down my throat. What really got me off was when I would go...

3 years ago
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Crossdressing camper

One rule about the park was no collecting of firewood, you had to bring your own. I would load up the bed of my truck with wood from brush pies and fallen limbs along the farm roads and I had plenty for the weekend and a little extra if anyone needed some. As darkness fell and the only light around was my fire, I slipped out of my bra and panties and t shirt and shorts and into a black satin camisole and tap panty set and put my shoes back on. I sat on the bench next to the fire and enjoyed...

3 years ago
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First Time Cross Dressing Experience

Hi everyone of indian sex stories dot net.This is my story how I got an opportunity to get my inner desires satisfied.I am from Kerala and I have come across very weird stages in my life, being groped by men and women which is why I think I am happy being a bi-sexual.Now moving along to the story. I met this girl name ‘Monica’ name changed who is an North Indian in an party in Mangalore and we exchanged numbers.Within a few months we we got very close and met her a few times again in...

2 years ago
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Tiffany The Cross Dressing Slut

I was at the swimming pool with a couple of friends and my cousin. I was 15 at the time, My Cousin, Mark, being 13 and my friends John, 14, Steve, 14, and Henry, 16. We were all drinking beers we asked a guy to buy us at a local grocery store, and were relaxing. We were all chilling in our shorts, with all our upper halves revealed, with John and Mark were the only ones to have six packs. Everyone was drinking, we were having a blast! 20 Min Later, we walk over to the Jacuzzi, and sit down...

3 years ago
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SRU Cross Dressing Blessing

SRU - Cross Dressing, Blessing By Lisa B "Damn it" Joe thought, "There isn't too many stores I know of which don't get suspicious when they see me looking at the lingerie section..." Joe had just wandered out from his usual store, after finding that they had no tights left on the shelves, and was heading towards the back of the shopping centre when he noticed a strange, awkwardly placed store which looked like it had just jumped out of a medieval fantasy story. Its dark...

3 years ago
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Started as cross dressing

This is my true story that happened with I was 26 yrs old. I am currently 28, married for 4 yrs now. I have been a horny guy every since I was in my 6th class and was always turned on by girls. I even made full use of the opportunity of co-ed and used to have fun with most of the innocent girls. I got married when I was 24 to a girl who was two years younger to me. She was a typical traditional girl with a very reserved and religious view of sex. She hardly liked variety and soon I discovered...

3 years ago
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My First Crossdressing Experience

Hi indian sex stories dot net dosto mera name jiya he aur ye meri pahli kahani he thodi bahot bhul ho jaye to maf ker dena. Me apne bare me bata du me ahmedabad ki rahne wali hu. Meri size 28 26 32 he. Aur me thodi gori hu aur me apni body her month wax kerti hu. Jise meri body ekdam girl ke jesi lagti he. Abe jayada time na lete huye story pe ati hu. Ye kahani 6 month pahle ki he jab meri college off tha. To me net pe search ker raha tha to muje ek post mili cd ki . Fire mene cd ke bare me...

3 years ago
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Malan Mothers on RehomeChapter 2

Esme rounded on her. "Marjory, girl, you have just GOT to tell us what that was all about! It sounded so weird, what you were saying, that we must know what the other end was. It sounded like your fella was on his knees!" Marjory started to tell her sad tale, about falling for her Derek, and making love with him, in the expectation that he was the love of her life and they would get married eventually. She had had a series of shocks. It was a shock to discover how unyielding her parents...

3 years ago
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Malan Mothers on RehomeChapter 10

He waited, then listened to a reply. "Right. Thank you. Please note that he is about to be arrested, so we don not want him leaving." He closed the call. "Thanks, Ruth, for reminding me. He will not be able to leave now. Now we just hav e to pick him up. Where will he be?" "This time of day? Probably heading out for his evening meal, either at home or in a restaurant. Do we know if he is married?" "The data we got for him does not mention any spouse, so presumably not," replied...

3 years ago
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Vacation on RehomeChapter 6

It had been three months since that fateful encounter with the erotic truffle, which had afflicted village schoolteacher Trevor Defreitas, Annabel Montford, a former pupil of his on Earth, her two younger sisters Tracy and Dinah, and their tour guide, Amelia Cross. That accidental exposure, in a shared meal, led to a night of drug-fuelled sex between Trevor and all four girls. Afterwards, upon considerable reflection, the girls realised that apart from all three sisters losing their...

3 years ago
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Vacation on RehomeChapter 10

George and Marina helped Georgina clear out her flat. Most of what she kept were pieces of inexpensive jewellery that she liked; her photograph albums; and mementos of Amelia’s childhood. George declared that it would be easy to copy the photos on to a digital file and keep them on a memorystick, as well as being available on her phone. They decided to deal with that on George’s computer at home. Georgina asked, “George, can we eliminate my late husband from some of the photos, when we put...

3 years ago
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Malan Mothers on RehomeChapter 11

"You may be right about us humans, but The Personalia have blossomed too. They have become more involved with Earth as time has gone on. They have adapted to capitalism with a vengeance. They own a number of business on Earth, and have almost entirely monopolised the audit sector of business: numbers are their forte, you see, and they have established a reputation for probity. I have heard rumours of them pursuing criminals and removing their stolen assets: much more effective than jailing...

3 years ago
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Vacation on RehomeChapter 11

Bob Kempe, the Governor of Rehome colony, was at his office when he received an unexpected call from the Personalia. “Governor, we have been analysing some of the statistical data that is compiled in major countries on Earth, and we have observed that there is a set of trends which may interest you. The statistics on crime contain data on assaults within families, and in recent months this has begun to decline, to an extent that indicates this to be a real effect and not a statistical...

3 years ago
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Malan Mothers on RehomeChapter 8

"That lady who escorted you here – Ruth I think you said her name was; can she sign an affidavit that there was no such intent?" "I expect so. There were a group of ladies involved in getting me and the girls together. They called themselves Malan mothers." Mrs Mboya's eyebrows lifted. "Ah. So that is who that lady is; one of the five Malan mothers? Derek – what is your surname, boy?" "Dearden, ma'am." "Mr Dearden, you have struck lucky. These ladies recently became famous in...

2 years ago
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True tales of submission and crossdressing Chapter Three Tale of Two Sisters

Another true tale... I've told it as accurately as I can from memory. Hopefully someone out there might enjoy this! Background ---------- The year was 2004. I had built up something of an online presence, with profiles on most of the personals sites out there - both as a guy, and as my girly alter-ego. That summer, two rather interesting women got in touch with me. Introducing Mistress Pink... ---------------------------- I had a profile on a well-known UK BDSM site. This...

2 years ago
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Vacation on RehomeChapter 5

Annabel asked the Governor, "Do you mind if I do the phone call? I think I can handle them okay, I really do." "Perhaps, but what would you say to them on this call?" "Just that things happened here, nice things, and that we have decided to remain on Rehome for the time being." Bob glanced over at Ruth, and asked, "Ruth – are you fine with this line?" Ruth looked thoughtful, then said, "Yes, I do believe that might be effective, if Annabel keeps her call simple and to the...

2 years ago
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Crossdressing the beginning

I would assume that for most men, interest in women’s clothing started at a young age. For me, this occurred when I was 11 looking through the Littlewoods, Gratton and Freeman catalogues that my mother used to have.At the time, I lived with my mother Jane, who was divorced, my brother Anthony and sister Sharon, who were five and three years older than me. It was quite easy to sneak one of the catalogues up to my room and thumb through them. If one of them had bothered to look at the catalogue,...

2 years ago
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Cross Dressing for Ann Again

About a week after my first amazing session with Ann, the neighbour from downstairs who blackmailed me into modelling her lingerie, I was again accosted by her on the stairs.“Hi,” she said, coming out of her front door as I was passing. “I’m glad I bumped into you” (I knew she was lying in wait behind the door watching out through the spyhole) “are you doing anything on Wednesday night?”I said I wasn’t and she said that as John and Ian (her husband and son) were going to Aberdeen to watch the...

4 years ago
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Vacation on RehomeChapter 3

Annabel, in her position as the Montford family head on Rehome, took the lead. “What do you mean, “think about what we do next”?” “There are several ways you might approach matters. One: if you feel that you have been raped by Trevor, you can have him tried by a jury here. I think you would have trouble convincing a jury, as you participated with considerable gusto, and he did not administer the drug either – I did, by pure mischance. So there is neither coercion nor intent provable...

2 years ago
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my first cross dressing play time

i sucked my first cock the other day. i posted a ad on craigs saying i like to cross dress and would like to find somebody to dress up with and take turns being sluts to each other and then i posted a few pics of me from my xhamster profile and actually got alot of replies. it took a few weeks but i finaly found somebody that like to dress up and he came over during the day and we started watching porn and i pulled out all my slut clothes and we picked out things that we wanted the other person...

3 years ago
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Malan Mothers on RehomeChapter 18

Fearn, if you would dispense the tea, and I pour the coffee, Nargo can assist with the milk jug. Right, girls?" Fearn and Nargo did a 'high five' and proceeded with their tasks, while the adults admired their dedication to these duties. As soon as the drinks were poured, Esme sent Nargo and Fearn to bring in the plates of scones, pancakes, and decorated cupcakes. Esme explained to her guests that while she had baked the scones last night, Fearn had done most of the pancakes and cupcakes...

4 years ago
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Vacation on RehomeChapter 7

"Hello, is that Mrs Cross? Or should I say, the former Mrs Cross?" "It is. Who are you, and what do you want?" "Madam, I am merely the bearer of glad tidings about your daughter." "My daughter? You know where my daughter is?" "Indeed, madam. Allow me to introduce myself more formally: I am Robert Kempe, Governor of the human colony on the planet of Rehome." "Rehome? Oh, yes I have heard of it. Why are you phoning me? Is my daughter in your colony, then?" "You are quick on...

1 year ago
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Vacation on RehomeChapter 17

"Oh, madam, I would never stoop to blackmail. I am not looking for any monetary benefit. I merely would appreciate some manly attention, at least for a while. Perhaps you could put in a good word for me, and encourage John in the matter, madam." Angelina thought for a moment, then responded, "Sylvia, If I were to suggest to John that I would not object to him paying some ... close ... attention to you, would that be acceptable? I will also say that your job is not in jeopardy, in case you...

4 years ago
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Cross dressing gay fantasy

I would wear black stockings and no other clothes. My whole body would be shaved. I put on cream that makes my skin look even whiter and blemish free. I want my skin to look as feminine as possible. I would wear a jet black wig like a messy bob. One were I can pull the hair over to partially cover my face. I would wear oversized black sunglasses with dark red lip stick and maybe some temporary acrylic nails. I sit on top of the kitchen work top with my knees up at my chest and feet crossed...

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