Wedding Gift

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.

Doug and I went through our school years together and were still good friends when we started college at 18. 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. 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 a young man, 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 I was a late bloomer! 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 stark 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 friend who was offering his ass. His 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 dreamt 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 college 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 college. Doug carried on dating the attractive girls. So Doug left college to become a trainer at an outdoor centre. I stayed on and 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 college 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.