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Doug and I had been best friends since the first day at school. Who knows why you choose your first friend? It could be that your mothers push you together. It could be because you turned up at the school gates at the same time. Or it could be because on the first day you sat down next to each other. All I know is that Doug and I were friends from the first day to, well right up to today. Through the first few years we were always in the same classes. We spent holidays at each other’s houses and our parents got to know each other pretty well too.

And then we hit senior school.

As puberty hit Doug became a bit of an athlete. He was captain of the football and rugby teams, he ran for the county and he was in the swim team. As you’ll imagine, he was a bit of a hit with the girls. He always had a choice of which girl to take to the disco and he seemed to choose a different girl each time.

Me on the other hand, well, puberty didn’t do me any favours. Puberty came late so I was on the small side. I liked playing sports but being so small compared with the other boys, I never got picked for any of the school teams. What I lacked in physical ability I made up for by being bright. I wasn’t a natural when it came to talking to girls, but with Doug around, he always made sure that I had a date for the discos.

As a typical adolescent I would get very horny when I got home from the disco and would play with myself. Seeing all those young, pretty girls dancing always got me really horny. But what really turned me on was watching Doug slow dancing with his latest girlfriend. It had started with me wishing I could be more like him and then the cool girls would be dancing with me. They would be resting their pretty heads on my broad chest. It would be their budding breasts and erect nipples held tightly to me athletic body.
Then one day I realised that it wasn’t Doug I was really jealous of. It was the girls.

I wanted to be held in his strong arms. I wanted to feel him cupping my buttocks through my thin dress. I wanted to feel his erection pushing in to my belly. I wanted to be looking deep in to his eyes as he kissed me passionately.

It was about this time that I started exploring my sexuality. When I was only ten, Suzy my elder sister wanted to practise her make-up skills and Jane, our other sister wouldn’t let her. I always got on well with Suzy and was more than happy for her to paint my lips red, to put blusher on my cheeks and apply mascara to my long lashes. I didn’t know what was happening at the time, but looking back at it now, I realise that I was having my first erections. Mum put a stop to these make-up sessions when I started senior school, but I still got on well with my sister.

The big film that summer had been Grease and the girls were all trying to be Olivia Newton John. They were all going for the look in the last scene in which she’s wearing those shiny black jeans. Doug’s date for the night, I think her name was Sarah, was wearing a pair of these jeans. They looked okay on her, but she had large thighs and they weren’t exactly flattering on her. As I was watching her dancing with Doug I could tell that he was getting turned on. He was holding her tight and his strong hands were squeezing her butt cheeks as he was grinding his groin in to hers. They were kissing passionately and I can’t deny that it wasn’t a little arousing. I was so jealous of Sarah. There she was in the sexiest of clothes and she had the best looking boy in the school playing with her body.

When I got home that Friday night I came like I never had before. I closed my eyes and pretended that Doug was stroking my ass in those tight black shiny jeans. It was me he was kissing. It was my hand that went down between us and stroked him through his trousers. I went to sleep that night imagining how it had felt for Sarah having Doug man handle her.

The next day I was going to have the house to myself and I knew how I was going to spend it. Suzy had persuaded Mum that she should have a pair of those jeans and I was going to try them on. I went to her room, found the jeans and sat down to put them on. I slid them up my legs, over my ass and did the button up. My erection was making an obscene bulge at the front of the jeans – not very lady like! But I didn’t care. I stood in front of the mirror and looked at myself. Without bragging, they looked fantastic on me – so much better than Sarah’s had and even better than they looked on Suzy! I stood on my tiptoes and twirled around. They felt so good on my bum and I just kept stroking my legs and ass, wishing it was Doug’s hands exploring my body.

Despite being only thirteen, I already liked to tease my own body so I didn’t take my erection out and cum. I knew I had all day to myself so I would enjoy myself with Suzy’s clothes. I pulled out a black training bra and padded it out with a pair of stockings (yes, both Suzy and Jane took after our Mum and preferred stockings). I found a black cropped t-shirt and pulled that over my head. Finally I sat at her dressing table and put on a little make-up like she had done many times on me. It took a couple of attempts but I finally didn’t look too bad. Some times it wasn’t all bad that puberty was still a way off! The only thing missing was a pair of heels. Mum wouldn’t let Suzy have high hells but she had a pair with a two inch heel which was plenty for my first time in Suzy’s clothes.

I walked down the stairs and started on my chores feeling like the sexiest girl in the world. I had the radio on quite loud as I was dancing around the kitchen, enjoying myself more than I thought possible. I was singing away at the kitchen sink and then I froze.

Staring at me through the window was Doug.

I don’t know who was more shocked. Doug’s face was a picture. He stood there open mouthed staring at me. I just screamed and turned and ran up the stairs as quickly as I could in those damned heels. I got to my room and slammed it behind me and dived on to my bed and just laid there and cried. My best friend had just seen me dressed like a girl. What would he think. I knew that he’d never want to talk to me again. I wouldn’t be able to look him in the eye. My day had gone from being the best day in my life to the worst in seconds. I cried and cried and cried.

I must have fallen asleep on my bed. The next thing I remember was the bed creaking as someone sat down beside me. As I laid face down on the bed not daring to look who it was, a hand started stroking my ass. I laid there pretending I was asleep. That hand was now sliding around my bum, stroking the top of my thighs, kneading me erotically. I couldn’t deny it. I was getting turned on and spread my legs a little so that Doug could reach between them. Yes, I knew it must have been Doug. He later told me that he ran back home in shock but when he got home he realised he had to come and make sure I was okay. When he saw me laying there in such sexy clothes he couldn’t help but start to play with me.

“I know you’re awake. And I know you’re enjoying it. I’m enjoying it too. You look so sexy in those girl’s clothes, you’ve got me horny. Here, look at how hard you’ve got me.”

I turned around and Doug was standing there with his hardening cock in his hand. I looked from his face, down to his cock and back up again. He smiled down at me as I lay prone on my bed.

“That’s right. You did this to me. You made me this big and hard. Here, feel what you’ve done to me.”

I reached forward and touched it. His cock was so much bigger than mine. Doug began to stroke himself slowly as I reached for his testicles. I had never seen hairy balls let alone held them. I had barely any hairs on my body yet and seeing him standing there almost fully grown was in stack contrast to me. Here I was in my sister’s make-up, wearing her clothes stroking my best friend’s cock.

“Oh that feels good. Do you want to stroke it for me?”

I couldn’t speak so I just nodded and reached my hand around his cock. I slowly stroked it up and down, looking up in to his face as he stood there letting me play with him. He started to moan as I picked up the pace a little. Whilst stroking him with one hand I played with his balls. His cock was getting longer as I stroked him. I was watching in fascination. I hadn’t seen a cock from this angle before and I was almost hypnotised.

Before I knew what I was doing I was leaning forward and licking the drops of pre-cum off his cock head. It tasted sweeter than I thought it would. I carried on stroking him and then opened my mouth a little to let the tip probe between my scarlet coloured lips. As his cock entered my mouth I started sucking a little to taste as much of his cum as I could get.

“Oh fuck that feels good. How do you know how to do that. Fuck I can’t stop.”

Doug had grabbed my head and was now pushing his cock deeper. I looked up in fear but Doug had his eyes shut. I tried to open my mouth as wide as I could as he pushed in further.

And then I felt him cum.

The first spurt went straight down my throat, deep in to my belly, as did the second and third. Doug then started to withdraw and the next spurt landed on my tongue. He then withdrew completely and a further three spurts landed on my face. I grabbed his cock and pulled it back to my mouth so I could suck it clean. I had been desperate for many months to be with Doug and I wanted to make the most of this opportunity. I cleaned his cock whilst looking in to his eyes with what I thought was love but was really lust.

“Jesus! That was amazing. I’ve never cum that much. I can’t believe what you just did for me.”
I leant back and licked my lips clean of his cum. I could feel his cum dribbling off my face. I must have looked terrible. I’m sure my make-up must have run all over the place. First day in make-up and I’d become a sperm whore!

“When I was stroking Sarah’s ass last night I thought she had the best ass ever. But when I saw you running through the kitchen earlier, I knew I was wrong. Can you show me your ass in those jeans?”

I grinned and stood up. As I’d spent most of the day in Suzy’s shoes, I was confident I could put on a bit of a show for my man. I strode across the room, rolling my cheeks as I went. I walked the length of my bedroom in short steps like I’d seen the models in the cat walk do. When I got to the door I looked over my shoulder and pouted at Doug. I opened the door and strode towards Suzy’s room and beckoned for Doug to follow.

I knew that I had to take advantage of Doug whilst I could so I jumped on to Suzy’s bed, got on all fours. I looked over my shoulder and saw Doug enter the room. His cock was hard again and poking towards his belly button. As he stood at the doorway he was stroking himself, staring at his little friend. His little friend who was offering his ass. His little friend who wanted to be fucked.

“You know we shouldn’t don’t you? I want to fuck you. I want to plunge my cock right up your virgin ass hole. I want to pump my spunk deep in you and make you my girl. I want to feel your ass milking my cock … but we shouldn’t …”

As seductively as I could I pulled those jeans down over my little bum showing Doug that I wanted him in me. That was all it took.

“You’re terrible … but I can’t resist you. I need to feel what it feels like to have my cock in your ass. You know I’ve never fucked a girl don’t you? You’ll be my first fuck … and you’re not even a girl!”

I was shocked. I thought Doug was a bit of a lady’s man. He’d been out with all of those girls and he hadn’t gone all the way yet. We were going to lose our virginities at the same time.

And then he walked slowly towards me. He guided his cock towards my rosebud. I could feel his cock head at my entrance. I looked over my shoulder and smiled encouragement. I could tell he was worried he would hurt me so I reached back and pulled my bum cheeks apart. His helmet popped past my sphincter and I pushed back to meet Doug’s forward thrust.

Now that he was in me he grabbed me around my waist and pulled me towards him. His hands around my waist felt so strong and firm. I went a little limp as I realised that I was finally being fucked by my best friend. His erection was sliding in to me as I let him pull me back towards him. It felt so good being used like a girl. I looked down between my thighs and past Suzy’s bra I could see Doug pumping in to me.

More than anything I wanted to feel Doug’s cum in me.

As he’d already cum in my mouth and over my face Doug wasn’t ready to cum yet. He was pounding my ass like the athlete he was. With every thrust forward I was pushing back as he was going deeper and deeper. I wanted to see his face as he fucked me so I rolled over on to my back. Doug grabbed my legs and pushed them against my flat chest. Holding my ankles wide apart so he could see my cum stained face, he kept thrusting in to me.

Looking deep in to his eyes and judging by the speed he was going, I knew that Doug was about to cum. His hairy balls were slapping against my ass.

And then it happened.

Doug started to fill me up with his semen. He grunted and moaned as he made me his girl. He kept pummelling my ass as his balls emptied their seed in to me. I’ve never been happier than when I looked up at him and saw the pleasure on his face as he filled me up.

Finally he stopped pumping in to me and let go of my ankles. I felt his cock soften and pop out of my ass. His cum was dribbling out of me on to Suzy’s bed. I dropped my legs and laid back with a satisfied smile on my cum soaked face and shut my eyes.

I must have fallen asleep as when I opened my eyes it was dark. I was disorientated when I realised I was in Suzy’s room. Had I dreamed it? Had I really sucked my best friend’s cock? Had Doug really taken my virginity? Had I been Doug’s first fuck?

Reaching between my thighs and feeling the wet patch on Suzy’s bed, I knew the answer to these questions.

I didn’t know what was going to happen at school on Monday. I don’t think I’ve ever been so scared. When I saw Doug he looked quizzically at me and smiled.

A smile was good.

Things had changed between us. We never had a repeat performance at school. Doug carried on dating the attractive girls at school. Puberty eventually came my way but I remained a small, thin frame. So at 16 Doug left school to become a trainer at an outdoor centre. I stayed at school, went to university and became an engineer.

And we drifted apart …

That was until about ten years later …

I had spent a few years at various engineering companies but had been made redundant. Things were so bad that I’d moved back home with my parents. I was very low. It came up in conversation at dinner that Doug was going to be back in town to visit his parents. Why don’t I go out for a drink with him?

Having not seen much of him since school I was a bit reluctant. My parents had told me that he’d done really well at the outdoor centre. It seemed that he had a real talent for it and was a natural at business. He’d left the outdoor centre and set up his own company which was doing quite well. I was embarrassed that he was doing so well and I was going nowhere. I decided I would be too ashamed to contact him so forget about it. But a couple of days later he paid a visit and insisted in taking me out for a night out.

I couldn’t believe how good he looked after all these years. He still had the athletic look about him but he’d added a smoothness to go with it. I could imagine that he still had his choice of
women and I knew that he’d be able to show them a good time.
So we went out for a meal and it was just like old times. Everything felt so natural and by the end of the meal it was like we’d never spent any time apart. Doug was telling me about how well his business was doing and told me that if I ever wanted a job, it was mine.

Well, I’m a proud man, but not a stupid man. I took him up on the offer just until I good myself back on my feet. And so I started working for Doug. I started as the office junior – setting up meetings with customers and suppliers, planning his daily schedule, looking after his diary, but was soon his right hand man and was talking to customers when Doug wasn’t around. Eventually Doug made me a partner. Of course if we hadn’t been old school friends, I’m sure he wouldn’t have done this.

Life was good. My confidence had returned. I had a couple of semi-serious girlfriends but nothing too serious. Despite being one hundred percent heterosexual to the outside world, I still enjoyed dressing up in sexy underwear and exploring my bisexual tendencies. I’d even given myself a new feminine name – Anna. None of the women I dated were important enough to me to share my other side with. So I was resigned to the fact that I’d stay single and keep Anna in the closet.

In the mean time, Doug was living the life. As I was taking on more of the workload, he was becoming a bit of a playboy. He had a string of stunning women which he dated. Everyone one of them was classy, well connected and the sort of woman you’ve be proud to take home to the parents. I still found myself attracted to Doug, but realised that our one time together when we were younger would remain that – a one off.

As part of his new lifestyle, Doug had the money to spend on property. He had a lovely house in our home town but had bought a flat in Brighton for when he needed to visit town. As we were now business partners and good friends again, I had a key for the Brighton flat and used it when I knew he was away. I loved the flat as it had stunning views of Brighton yet had privacy.

Whenever I used the flat, Anna’s wardrobe would come with me. I would spend the weekend dressed from underwear through to my favourite dresses. I’d be shaved from my eyebrows down, paint my finger and toe nails scarlet red, be in full make-up the whole weekend and take a selection of wigs. Absolute heaven!

I always made sure that Doug wouldn’t be coming to town and that I’d leave no trace of what I got up to. Even if I had left something behind I’m sure that Doug would assume that I’d got lucky and had taken a lady back to the flat.

I loved those weekends as Anna.

Until one summer weekend. I had spent the day in a new white bikini on the balcony working on my tan lines. I had got out of the bath having had a nice glass of white wine whilst having a long soak and stepped in to a short silk nightie ready for a night curled up with the rest of the wine and a good book. With the music playing quietly I heard a key in the lock. There was nowhere to go, nowhere to hide as the door swung open and Doug walked in.

“That is you isn’t it? I suspected that you were using the flat as a love nest. Whenever I use the flat it smells of perfume and I found a pair of lace knickers under the bed. You’ve improved a lot since we were at school together. I still remember that time we made love together. You made me the man you see before you.”

I didn’t know what to say. I couldn’t deny anything could I? But he had called it making love. He could have said “When I fucked you.” but he thought we were making love. Even now my heart flutters a little knowing he looks back at it with fond memories. The fact we’d never spoken about it since had made me think he regretted it.
“So what do I call you now?”

“Anna. Please call me Anna.”

“Well Anna, I’m sorry to have interrupted your weekend. I’ll find myself a hotel for the night and we can talk about this at work next week.”

And with that he walked out.

I didn’t know what to expect when we got back to work. I walked in to his office and sitting opposite him was a lady. She had long blonde hair, breasts which her top was struggling to keep decent, a miniskirt which would barely cover her backside and a pair of platform stilettoes which wouldn’t look out of place on one of the girls at a pole dancing club.

“This is Nikki. She’s my fiancée.”

I didn’t know what to say. I had assumed that she was a new client. But she was going to be Doug’s wife. She was so different from the women he normally dated and he was going to marry her.

“I know what you’re thinking,”, I was glad he did as my mind was rushing all over the place, “How come you’ve never mentioned her before? Well, when I left the flat on Saturday I walked around a long time thinking about what we were going to do and I found myself in a bar I’ve not been to before. As I bought myself a drink, Nikki was standing beside me and I offered her one too. Well, we spent the night talking and had a so much in common. One thing lead to another and I realised that Nikki is the perfect woman for me. She has everything that I’ve been looking for in a woman since I was a little boy.”

“Well Nikki, it’s lovely to meet you. I’m sure we’ll be spending a lot of time getting to know each other.”

“So glad to meet you too. Doug has told me all about you. I just know we’re going to be such good friends and be very close.”

With that Nikki gets out of the chair, walks over to me and gives me a big hug. I feel her huge breasts squeezing in to my chest and I look over her shoulder at a grinning Doug as she pecks me on the cheek. As she walks out of the room I turn around and see Nikki adjusting her short skirt so that it just covers her stocking tops.

“What do you think of my wife to be?”

“She’s quite some girl. Don’t you think you’re rushing in to this?”

“Definitely not. I’ve always gone on my instincts. You should know that! As soon as I laid my eyes on her I knew that I wanted her to be the woman I spend the rest of my life with.”

“So when’s the big day?”

“As soon as we can arrange it. Of course, you’ll be the best man won’t you?”

“Doug, it’d be an honour.”

Nothing was mentioned about that night in the flat. Anna had stopped visiting Brighton. She remained in the closet in my house, desperate for the next chance to surface.

At least nothing was mentioned until the stag do. We were in a club in Amsterdam with the whole group. Doug had stepped outside for a bit of fresh air and I’d gone to keep him company.

“I don’t know how to start this conversation. I have a big favour to ask you.”

“Go on. You know I’d do anything for you. You saved me when I was at my lowest.”

“Well, it’s my brother Nev. He’s desperate to be my best man. I know it’s short notice, but you wouldn’t mind would you?”

Inside my heart was broken. I wanted to play a key part in the most important day of his life.
“Of course not Doug. It should be Nev. I was always surprised you asked me in the first place. It would have been an honour.”

“Perhaps I can ask you a further favour. This one’s even bigger. You’ve been my best friend for ever. You were my first lover and I want you to be there on the day. Having met Anna, would she like to come to the wedding and be the maid of honour? Nikki lost contact with her family and she has no one who means as much to her as you mean to me. As Anna you’ll be part of our big day and I know she’ll make a big impression on our guests.”

I was stunned. I didn’t know what to say.

“Umm … Sure … Why not?” What had I agreed to? “But how will we explain me not coming to the wedding?”

“I thought about that. We’ll say that you were so upset about not being the best man that you refused to have anything to do with the wedding and you’re going to take a break from the office whilst you consider your future.”

“Okay Doug, let’s do it.”

I lent forward to give Doug a hug and was shocked when Doug instead gave me a long kiss. As his tongue probed inside my mouth he grabbed my but and pulled me towards him. Much like all those years ago, I could feel his erection crushed against me. I reached down to grope his cock and could feel it pulsing through his trousers. As I looked over his shoulder I could see Nev walking towards us and I pushed Doug away and shouted at him,

“Fine! If you prefer Nev to be the best man, you can shove it.”

Doug looked at me and realised what was going on and winked at me before Nev got to him.

“Don’t over react. Please come to the wedding.”

So I turned on my heel and left them there.

When I got back to the UK I realised I’d have to spend the next few weeks being Anna full time. I would hate to embarrass Doug on his big day. It would be terrible if people worked out that the girl next to the blushing bride was a man underneath her dress. I don’t know who Doug told Nikki I was. When I got home I packed up Anna’s things and moved in to the flat in Brighton. When I got there, there was a message from Nikki telling me we needed to go dress shopping for my maid of honour’s dress. So the next day that’s exactly what we did. This would be my first day outside fully dressed as Anna and I’d be going shopping for a maid of honour dress. I’d be in a changing room with a sexy woman trying on many dresses whilst trying to hide my secret.

What should I wear for this shopping trip? I could wear a knee length skirt and go for a classy look. I could go for designer skinny jeans as they’d hide my secret but might be difficult to get on and off a few times without anything popping out. In the end I settled on a pair of black leggings with a flowing skirt over the top and some control panties underneath to keep things hidden and a cropped top.

When Nikki turned up she looked amazing. So different from the first time I met here. She was wearing a lovely skirt suit that showed off her best features – her legs and her boobs. I was glad I’d put the control panties on as my cock was straining for release. Doug was going to be a very lucky man to be taking this lady as his wife. Nikki came up and gave me another big hug. I loved the feeling of her breasts against my flat chest. I wished I had breasts like these, but it would like strange underneath my work suit.

“Lovely to meet you Anna. Doug has told me that you’re his cousin. So nice to finally meet you.”
I was pleased that Doug had come up with a story.

“It’s a honour to help you out. Doug and I were very close as c***dren and I’d do anything to make him happy on his wedding day.”

And so we hit the shops.

Nikki had Doug’s credit card to buy the whole outfit. We tried a few shops and the dresses were going on and coming off in quick succession but we couldn’t find anything that fitted well and we both liked. Fortunately all of the changing rooms were so small there was only space for me so I had no problem hiding my true sex from Nikki. Finally we went to a designer shop which had an open changing room. I didn’t know how I was going to hide the truth from Nikki. Nikki had selected a tight fitting dress with a skirt stopping a couple of inches above the knee. I turned my back to Nikki and took off my top and stepped in to the dress. As Nikki pulled the zip up she said to remove the leggings.

“You’ll have to take those off as we want to see how you’ll look on the day. You take them off whilst I go and find some heels to show off your lovely legs.”

While I had the changing room to myself I pulled the leggings off and stood there checking myself out in the mirror. The dress did look wonderful. It showed off my slim figure and squeezed a little bit of cleavage out of my flat chest. I loved the colour, the material and the cut. Looking at myself in the mirror I knew I’d make a pass at the woman I was looking at if I met her at a wedding.

When she came back in Nikki had taken her jacket off and had a pair of heels in her hand. As she knelt in front of me to help me with the shoes I couldn’t help but look down her bountiful cleavage. I had to lean on her shoulder as I stepped in to the shoes. As Nikki looked up she smiled at me.

“Wow. Don’t you look fantastic? You’re going to have the men falling at your feet if you wear this. If you play your cards right, the women will be giving you their numbers too.”

I was so horny now.

“Of course, we’ll have to do something about this.” And she slide her hand towards my groin. “We can’t have a bulge like this showing up can we?”

Nikki slid the skirt of the dress up my thighs until my panties came in to view. Looking up at me she moved the panties aside and out popped my erection. Without breaking eye contact Nikki took my whole length straight down her throat in one swift movement.

“Oh Nikki, we can’t do it here. What if someone comes in and finds us?”

She didn’t seem to care. I looked at the mirror and saw a cute, skinny girl with a cock poking out from underneath her skirt being sucked off by a gorgeous girl on her knees with the biggest breasts I’d been luck enough to see. Nikki’s head bobbed up and down on me leaving her lipstick all over my girly cock. Having spent the day as Anna and trying on some of the sexiest clothes I’d ever worn, I knew I wouldn’t last long.

“Nikki, I’m close. Oh Nikki … Please don’t.”

Nikki had reached around and was pushing a finger in to my ass. I couldn’t hold back any more and I shot my spunk straight down her throat.

“There. That’s better,” she said as she popped my cock back inside my panties and pulled the skirt back down, “No bulge now.”

Nikki looked up at me as if she picked a bit of fluff off my skirt but she’d just given me the best blow job I’d ever had.

We bought that dress and the shoes. Before we left the shop Nikki had me try on some new underwear.

“We can’t have you turning up in those horrid control panties. My maid of honour needs to be wearing something as sexy as she is. You never know who might get to see them.”

Before returning home Nikki insisted we both had matching manicures and pedicures. We also paid for me to have hair extensions. My hair was now as long as her hair but I was a red head to her blonde.

“You know that Doug will want his two favourite girls looking their best. He says he thinks of you as his little s*s, which will make us sister-in-laws.”

After we’d finished our shopping we found a quiet restaurant for a well deserved meal.

“Nikki, I have to ask. You didn’t seem very surprised when you spotted my bulge. Did you know that I wasn’t all woman?”

“Do you really think that Doug and I have any secrets from each other? He told me everything about you. He told me about the time you made love when you were at school together. He told me how close it made him feel to you. I know that he’s missed that closeness.”

“Did he really. We never spoke about it at the time so I assumed he regretted it. I wish I’d known all of theses years.”

“Don’t worry Anna. The important thing is that you know now and he’s accepted who you are. Between you and me, I admire you. You’re so naturally beautiful. Spending all day with you has made me horny all day. When I got home tonight I’m going to need a good fucking and Doug is just the man for that … as you know. Here, I’ve been dripping wet all day.”

Nikki reach under the table and slide her hand beneath her skirt. When she brought it up I could see her fingers glistening. She put her fingers in front of me and I sucked them clean as if she’d offered me some cream off her cake. She smiled as I and wrapped my tongue around each finger and sucked them clean.

“Oh I bet Doug loved it when you did that to his cock. So Anna, have you bought us a present yet?”

“Not yet. I didn’t know what you’d like.”

“Oh, that’s easy. We want you Anna. Will you share our bridal bed? I know that Doug wants to have your lips around his manhood again. He wants to feel his shaft pounding in to your womanly ass. He wants to see you make love to his new wife and I know that I want to feel you inside me. To have you pumping with your girly cum. Would you like that Anna?”

“Of course I would. I’ve only made love while dressed that one time with Doug. For him to be there the second time and have you there with us. Do you really want me there on your wedding night? Your wedding night is meant to be special – the first night with the partner you’ll spend the rest of your life with.”

“That’s why we both want you there tomorrow night, Anna. We both want you in our lives. Do you want that to?”

“I do Nikki. I do.”

The next day was a blur.

I remember seeing Nikki walking out of her bedroom in a princess wedding dress. The low cut line showed off her breasts wonderfully. The tight body revealed what great shape this lady was in and her make-up and hair was to die for. Every time I looked at her and thought that tonight I would get to mount this woman. I would be sliding my girly cock in to her pussy whilst Doug’s cum would be dribbling out of my ass and down on to my sheer stockings. I couldn’t wait to see what Nikki had hidden under her dress. I hoped she’d be wearing a lacy white basque, sheer white stockings and white panties soaked through with her sweet cum.

I remember walking down the aisle watching her lovely ass swaying inside that dress. I was hoping that my dress was having a similar effect to the wedding guests as they watched me following Nikki.
I remember crying my eyes out when my best friend married the gorgeous girl I was hoping to know better and better. I had to play a quick visit to the ladies to sort out my make-up.

I remember sitting next to Nev at the wedding reception. He couldn’t keep his eyes off me. And when we shared a dance he couldn’t keep his hands off me either. It was strange. All those years ago I had wanted to be the one dancing with Doug at the school disco now here I was dressed up in a tight fitting dress, dancing with his little brother. Of course I did finally get that dance with Doug. He held me tight as we had a sexy slow dance.

“Nikki told me you’d agreed to be our present tonight,” he whispered in my ear, “You don’t realise how many years I’ve waited for this night.”

As he grabbed my ass and pulled me closer, I couldn’t resist squeezing my hand down between us and grabbing his cock.

“Tonight, my love, this is going to be fucking me. Your cock is going to be balls deep in my ass as I give myself to you. You’re going to make me moan like the lady you want me to be. And do you know what? After that I’m going to make love to Nikki. I’m going to fill her pussy up with my cum. I’m going to get her pussy nice and wet before you slide this big cock in my hand now deep inside her. My cum and you cum will be mixed inside her pussy and then we’ll both get on our knees and lick her pussy dry. See you later my big lover.”

And with that I left him on the dance floor with a big bulge in his trousers. Luckily for Doug, the dance floor was dark enough for no one to notice.

Like all weddings, the guests started to drift away as midnight approached. Nikki and I went to the ladies to fix our make-up. Watching her apply her lipstick, I couldn’t resist giving her a kiss. It all got a bit out of hand and by the time we’d finished the kiss, we both had to reapply her lipstick.

By the time the last of the guests departed, all three of us were ready for our night of passion. We left Doug at the bar sorting out some champagne whilst we went to the bridal suite to prepare ourselves for our man.

As I opened the door Nikki grabbed my hand and dragged me on to the four poster bed. We had our hands all over each other when Doug entered the room.

“Heh, don’t start without me. I want to see you two stripping each other off.”

I turned around and let Nikki pull the zip down. I stepped out of my dress and was left standing in my new matching bra and panties. My four inch heels showing off my sheer stockings, which were being held up by the matching garter belt, to perfection. I could feel Doug come up behind me and start nibbling on my neck as Nikki pulled my knickers to the floor. As her lips engulfed my erection I felt Doug’s cock sliding between my ass cheeks. I could feel his naked flesh against my back. He must have got out of his suit in record time.

So here I was. My best friend’s cock ready to invade my ass for the second time and his new wife sucking my erection whilst I was standing in a bridal suite dressed in stockings and the most expensive underwear I’d ever seen. I was one happy girl and ready to feel Doug’s cock inside me. I knew it was going to hurt when he entered me, but it would be worth it.

Looking down at Nikki with her lips brushing against my balls, I couldn’t believe how she took all of my cock down her throat. I wondered of she could take all of Doug’s cock down her throat and knew that by the end of the night I’d find out.

“Are you ready for me Anna? Do you want to be part of my family? Can I enter you now my baby?”

“Oh yes Doug. Make love to me. I want to feel you pumping in to my ass whilst Nikki sucks me. Now please Doug.”

And he did. He slide his cock in to me gently and tenderly. Inch by inch he stretched my hole. I panted quietly as I felt full again. This took me back to that day many years ago in Suzy’s bedroom when he last took me as his woman. This time we were older. We were wiser. We were also sharing the bed with his new wife.

I didn’t want to cum down Nikki’s throat again. I wanted my fill her pussy with my girly cum so I asked her to stop sucking me as I couldn’t hold back any longer.

“Here Nikki, turn around and lets get that dress off you.”

I pulled the zip down and helped Nikki out of the dress. With her back to me I could see the basque I had been hoping she would be wearing. I could see those white lace top stockings and some silk panties.

Behind me Doug was pumping harder in to me. He was groping my flat chest, pinching my nipples.

“We need to sort these out soon. If you’re going to be spending time in my bed, you’ll need to have implants.”

I couldn’t believe what he was saying. Doug wanted me to be more like his new wife than I had been prepared for.

“How big Doug. Do you think I can have breasts as big as Nikki?”

“Oh yes Anna. Your boobs will be as big as Nikki’s. You two will pass as sisters and will be able to share each other’s clothes. You’d like a sister wouldn’t you Nikki?”

“I’ve always wanted a sister. You’ll be just about perfect. Other than the hair colour, we could be identical sisters.”

“Well except that I have a cock and you don’t.”

Nikki turned around and then I saw it. Nikki reached inside her knickers and pulled out her own erection.

I just laughed and reached forward so that I could get my lips around this gorgeous lady’s shaft. I wanted this new husband and wife to fill me with their cum at the same time.

“You don’t know how difficult it was in the restaurant last night. I wanted to take you in to the ladies and show you how much I wanted you but I promised Doug that I’d wait until tonight.”

And that was how we got together. Apparently when Doug had found me in the flat in my nightie he had gone straight to a transgender friendly bar in town looking for a woman to replace me. That was where he found Nikki. The next morning when he was laying in bed having been fucked in the ass for the first time, he told Nikki what had happened. She told him that she wanted him in her life but she knew that Doug wanted me in his life. This way they would both be happy. And once she met me she just knew that I’d be happy with both of these people in my life.

We’re still together. Doug is the bread winner. Nikki and I are kept women. I had my implants and we’ve never been happier. We’re thinking about having a c***d together. We’re looking for a clinic which will take a sample of sperm from all three of us and find a surrogate. All three of us would then equally be the parents.

For those who want to read the details, I could be persuaded to write and tell you what happened on the wedding night and adventures we’ve had since.

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Wedding Day

Wedding Day Susanna says: - It is every T-girls fantasy to get married in a lovely white wedding dress, to wear those wonderfully sensual white and pearl bodices, the white stockings and the blue garter. The icing on the cake in this story of course is the photographer, what a way to celebrate your first few hours as a married woman, by being fucked by a man! As for me, always the bridesmaid but never the bride, especially when I wore a lovely pink taffeta bridesmaids dress that hugged...

4 years ago
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Wedding night with the bridesmaids Part 1

Still dressed in our wedding attire we stopped back at our apartment. We made it up the elevator to the 5th floor, laughing as we passed some people congratulating us. There were some gifts labeled “Congratulations Shane and Kelsey” on the center island as we walked into our place. The apartment was more than we could afford as it was a new fancy unit. The entrance opened up to a very open kitchen with a small nook where you could sit, take off shoes and hang your coat. If you walked in a bit...

2 years ago
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Wedding Night With No Wedding

She blew her hair from her face and looked at the flat tire, she then looked down at the white dress she was wearing. She then started to cry and that was how he found her. "Miss?" Kimberly turned around and wiped a tear from her cheek, before looking up at the man in front of her. "Yes?" she asked, though she knew what he was going to ask her. Frank looked at the woman before her, gauging her age to be about thirty, perhaps thirty-five, either way it was an age that seemed a little...

2 years ago
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An Unwanted Gift

AS I ALWAYS TELL YOU THAT JUST ENJOY READING THESE STORIES AS A HARMLESS AVOCATION BUT NOT AT THE COST OF YOUR RELATIONS AND LIVES. I WARN YOU THIS TYPE OF RELATIONS ARE PROHIBITED AND ARE FAR AWAY FROM THE REAL LIFE. ALL THE INCIDENTS AND CHARACTERS ARE FICTITIOUS.THIS IS INTENDED TO ONLY PEOPLE WHO ARE ABOVE 22 YEARS. THE FOLLOWING FICTITIOUS STORY CONSISTS OF EXPLICITLY i****tUOUS STORY. ANY PERSON WHO IS SENSITIVE OF family RELATIONS AND BELIEVE IN MORALS DO NOT READ THIS. KEEP AWAY.THE...

4 years ago
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The Gift

The Gift by Brad Miller Hey, have you ever wondered what it would be like to be someone else? It was never something I really thought about until a couple years ago when my father told me about my very special gift. A gift that is passed from every male in the Edward's family to another. I inherited it from my father. And I am forever grateful for it. ---------- "Dammit Sean! Would you turn that fucking music down?", my sister, Alicia screamed. "Hell no! I'm trying to...

4 years ago
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A Wife8217s Gift

Hello friends, here is a story that will make your cocks hard and your cunts wet. A loving wife gifts to hubby his sexy sister on her wedding anniversay. I came writing it, I hope you cum reading it. Email me at I am very open with my older sister Sarita who is married to businessmen Sahil. They have two kids and they are studyng in school. Sahil is most of the times traveling and Sarita often spends some time with my wife Ankita. My sister loves her Bhabi (brother’s wife) and so does my wife...

Incest
1 year ago
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Amlu Aunty8217s New Year Gift

Hello, All, Indian Sex Stories readers. How are you all. Thanks for your huge and overwhelming response for my first sex story. I am happy that many of them read my sex story and informed about your satisfaction. Thanks to the Aunties and girls who invited to their house and mutually satisfied with new positions and new things and looking forward to satisfying you all to my best with the confidentiality. All your feedback are welcome. You can email me or chat with me in and will reply ASAP to...

2 years ago
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Wedding BetChapter 8 Wedding Reception and AfterParty

Mindy and I used exactly what Margo had written for us to say as our vows. Mindy liked the words as much as I did. I read the version first only by tradition. “I believe in you, the person you will grow to be and the couple we will be together. I take you as my wife, my best friend, my mentor, my role model, my accomplice, my playmate, my confidant, and my greatest challenge. I will always respect you, encourage you, cherish you, and love you more each day. “We have started this union as an...

4 years ago
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Birthday Per Diya Didi Ne Anmol Gift

Hi, friends kaise hain ap sab log nd umeed karta hu ki thik hi honge.jessa ki ap jante ho i m rahul nd my sweet sister palvi. ap sabne meri stories jo iss per publish ho chuki hain ko bahut passand kiya or muje mail kiye jinne read kar main or meri didi palvi bahut khush huye or unmain se kuch mere frd bhi bane jessa ki ap sab jante hain ki main or didi ek dusre ko bahut like karte hain or hum sex bhi karte hain hum dono apne is sex se bahut khush hain or chahte hain ki hum sada karte rahain....

3 years ago
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The Birthday Gift

Your birthday party had been great fun. We’d met some friends in our local. We’d had a good laugh, and maybe drunk a little too much. But hell it was your birthday. I hadn’t known what to get you for the occasion; I wanted it to be something memorable. But what? Clothes? I would choose wrong. Perfume? You had a dressing table full.  Underwear?  To easy.  But what? Then your eyes had lighted onto something in the pub and I knew! I knew what I could give you, that would make you smile, make you...

4 years ago
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Wedding Training Part 1

Story2 Sandra Fane was delighted when her daughter, Alison, announced that she was to wed. Her chosen spouse was Alan, a boy she had first met at school, and had developed a growing attachment to as time went on. He was ambitious and ran his own business, although at times, Alison felt she had absolutely no idea what he was up to, it seemed to involve buying and selling virtual things at the right time, and making money out of thin air. Alan tried to explain, but said that a key aspect...

1 year ago
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Wedding Celebration

I really miss the weddings, especially the desi styles you could see. This was an incident when I had been to my cousin's wedding with my parents. I had the best fuck with one of the milf in the wedding, later I got to know that she's a far relative of mine. I was in the 3rd year of my engineering, born and groomed in Bangalore.I had been invited to my cousin's wedding close to Bangalore called Hassan.It was a wedding celebration to remember, which was in his farm house.Everyone who were...

MILF
4 years ago
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Wedding Day

Doe is so happy to be marrying you, so excited about the wedding. She wanted to make the wedding as special and wonderful for you as you know it will be for her. So Doe agreed to make this your fantasy wedding, the wedding of your dreams. She let you plan out whichever details you wanted, and she planned the rest. You got to plan the guest list. Standing at the alter, looking out over the rows of guests, you see a crowd of beautiful women, all dressed up in their prettiest dresses, hair done...

2 years ago
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Wedding Seduction Episode One

Lisa came to the wedding with only one thing in mind. She wanted to get laid. Lisa didn't know the bride well, but was well acquainted with the groom. She had lived with him for a year before he met his bride. She became very close friends with Barry even after the breakup. That's why she received the wedding invitation. Her dilemma was how to wear something seductive, yet wedding appropriate. It couldn't be a "fuck me" dress, but an "I'm a slut who's looking" gown. Lisa chose an outfit that...

Straight Sex
4 years ago
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Wedding Daze

Wedding Daze By Legion Many His hands laced through the straps of my garters as his fingers slipped between my white stockings and my smooth legs. I could feel the rough netting of my crinoline get crushed under the weight of the two of us and didn't care. He was mad for me he wanted me and would ruin my wedding dress to have me and I wanted him to destroy it as he took my maiden head. "Cut off my skirts with your knife, Phil," I whispered into his ear as he ground into me with...

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