A short part of a person’s life, but was he totally surprised by the outcome or was he leaning that way and just needed a push? Were the girlfriend and his date in league together? But most importantly will the experience change him forever?

We had been together for a year and I thought we were doing fine, I had moved into her flat when my lease came up for renewal and after a few teething problems we got used to sharing her flat all the time. That was until two weeks ago we had had our Saturday night sex and I thought it was ok but she clearly did not, can you believe it she turned to me and said ‘Rob, there is no easy way to say this, you are pretty useless in bed, you never consider what I want, it is just play a little then you get stiff and thank you I’m done.’
‘But I thought was what you wanted?’
‘Like you ever asked.’ She replied tartly. ‘Anyway I have been thinking and I reckon it would help if you got to see things from the other side.’
I was confused now ‘How?’
‘Oh easy, Marcus has agreed to take you out and show you a good time.’
‘What!’ Still confused ‘Marcus is gay, nice bloke but,,,,,,,,,,oh I get it, you want me to be his date and let him flirt with me.’
‘Not quite, I want you to be his girlfriend and go on a date with him. He will treat you like a woman and hopefully you will do your best to respond like a woman.’
‘But, but, but, I am a straight bloke.’
‘Is that what you think, all that body lotion and special soaps, you even have manicures.’
‘Well that is because they are good for me. Anyway what makes you think I will agree?’
‘Because little Robby’ her voice went quite stern ‘if you don’t you will not be coming near me with that’ she squeezed the end of my limp but tender dick ‘and you will need to find yourself somewhere else to live.’
‘But that is a bit harsh, date Marcus or else, what kind of a deal is that?’
‘One you have to agree to or leave.’
‘But what if I just listen to what you want.’
‘No deal, you never listen anyway.’

Well that was two weeks ago, by the following Saturday I had not only agreed to her crazy idea, but had accepted what she termed training, which was supposed to help me pass more easily as a woman, Marcus was not wanting to be taking a horrible bloke in a frock out. It started with spending Sunday walking about in heels, but as the week progressed the heels got higher, I lost all my body hair, she plucked a few hairs from my eyebrows and on Thursday so I knew she was serious, with a mixture of superglue and tape, pushed my balls inside me and secured my dick so it faced backwards. It would swell a little but the worst was having to sit when I peed, just like a girl. When I complained she kissed me and said ‘perfect’ in a very satisfied tone.

Saturday itself was a day full of new experiences. My first was to feel what it was like to have a bust and be grateful for a bra, the glued on prosthetics pulled at my chest unless they were supported. Then there was the sensations of wearing a satin thong, a matching black corset and fine stockings. My trapped dick wanted to come and play in response to these delights but I just had to sit on it as it were. I had always loved my hair and taken care grooming it, it shone like a girls my mum had once told me which I was quite proud of and now it was quite long, I am sure she would have said it looked like a girls. Beth washed, conditioned then adding some new products before rolling it onto rollers and leaving me to sit under her hair drier hood until she was happy it was ready. As she unfurled the rollers I could see my normally straightish hair had some serious wave going on and I remember thinking, ‘that looks good’ but she then starts backcombing and pinning it up in a pile on the back of my head. So much volume and with just enough tendrils escaping round the edges.

Next she informed me that my ears were to nice to go unadorned, so with a block of ice and a needle I was given the addition of a couple big pearl studs. ‘Classic’ she told me. I think I agreed with her. It was about lunchtime by now and all the ‘training’ and now Beth’s pampering was making me feel quite different, even feminine. So it was no surprise to hear Beth tell me I was mistakable for a woman already, my hair was up, I was wearing some sexy underwear I once bought Beth and sitting rather erect due to the corset and involuntarily stroking my stocking covered legs which felt so nice.
‘This feels rather nice, why do you never dress like this?’
‘That is the point, if I go to all this trouble, yes it feels nice but you never appreciate it, you never compliment me, and when I do it makes no difference, you treat me the same as you do when I am in jeans, so why bother?’
I apologized.

Lunch over, and it was back to completing my transformation so I can stop with Beth. She glued some long nails to my fingers and painted them a deep shiny pink, matching my toes. I thought I must be nearly done as she set about my face with cosmetics, base coat, blusher, powder, eye brow pencil, eye liner, various silver shadows round my eyes finished off with a few layers of lengthening sticky mascara, and last the same deep pink colour lipstick as my nails was applied to my lips but with an extra coat of clear she said would make a huge difference, initially it just made them look wet and glossy but then my lips started to tingle and swell, my normal narrow lips pouted without me doing anything. I looked completely different but did wonder what sort of signals the way Beth was dressing me would be giving off. When she pulled the zip up the back of the fitted dress I got my answer.
‘Now then Robby, slip into the heels, a dab of perfume and these pearls and I think we shall have it.’
‘Have what?’
‘Restrained sexy.’
‘Pardon.’
‘I think I have made you look like the sort of woman men take a second look at and think they wish they were with someone like that, because you look good but also because you look like you are enjoying flaunting your sexuality without being a tart.’
‘What!’
‘Marcus like I said will treat you as a woman, you need to respond like a woman and a sexy woman is always a good place to start.’
‘You think I look sexy and so I should act that way?’
‘No should about it, you will act sexy, act like you wished a girl would behave for you. I expect you to flirt, encourage, kiss, cuddle, flutter your eyes, whatever it takes to make you look sexy and for him to feel he is the most special person in the world.’
‘But.’
‘I know you are unfamiliar with most of this but that is why you are doing this, and if you don’t and Marcus comes back saying you were a right moody miserable cow then don’t bother coming back and expecting a welcome.’ The reality of what I was supposed to be doing just hit home. ‘Got it?’
‘I think so.’ I replied in a rather weak submissive tone.
‘Ok you have until seven to get that sexy wiggle into your ass, and some grateful attitude into your demeanor. So I suggest you get in front of the long mirror and practice.’
I was just about to ask if I could have something to eat, when she appeared with a drink for me, I looked at the clear liquid.
‘Gin and tonic. Get you in the mood hopefully.’
I took a sip, it was a strong one but nice and I would need some dutch courage.

Seven came and I had been resting for a short while, though a corset hardly lets you lounge, I sat upright as I was encouraged to by Beth and the underwear. My feet ached a bit but I had got the wiggle as I walked by dropping my hip as the weight transferred. She gave me a final pep talk about making sure he felt special and to let him take the lead but saved the most shocking to last, a small clutch bag with a little cash, a few bits of make up for repairs, my phone, I was fine with these, but the tampax and a condom were there as well. Her explanation, all real women carry a towel, and all sensible women on a date carry a condom for just in case the guy is not well prepared.
The penny did not so much drop as crashed. ‘You want me to let Marcus screw me?’ my mouth somehow did not close as I further realized just what Beth was setting me up for.
‘But that is the whole point, I want you to be on the receiving end and learn what it is like to be a woman.’
‘Ok right got that, but sex?’
‘And sex, I don’t expect you to let him just screw you anywhere, he will have to take you somewhere nice, the back seat of a car is never good.’
‘But he is gay.’
‘And yes you only have one hole down there and not two like me, but he prefers the one hole arrangement and who knows you might be like plenty of men and women and actually like the feel of something deep inside them.’

Just then the door bell rang and a casually dressed man I knew as Marcus stood there, he kissed Beth on both cheeks who then stood back and introduced me. ‘Marcus, this is Roberta.’
‘Gosh Roberta you look fantastic.’
I tried to look coy and angled my head down and looked up at him with a smile on my lips. ‘Call me Robby please.’
‘Ok Robby, are you ready?’
I picked up the bag ‘As ready as I ever will be.’

Beth never gave me a kiss or even a farewell word as Marcus took my hand and lead me out to his car. I was sure every nieghbour would be watching and laughing at me as I made my public debut but it passed without a hitch. Once I had overcome the technical problems of getting into a car in a tight dress and heels I relaxed a little.
‘Right then Robby let me just get this straight, this is your first time out in public as a woman?’
I nodded.
‘And you want to experience as much as possible the female side of a date?’
I nodded thinking it was not quite how Beth put it but close.
‘And just to be sure, Beth is ok with her boyfriend going out with a gay bloke while dressed as a very attractive woman?’
‘It was her idea and it was she who dressed me like this so she must be ok with it. And less of the attractive please I am sure there are lots of better looking women about than me.’
‘Not that I look so much, but you do look very convincing and believable as a woman maybe just keep your voice softer and you could pass as the real thing.’
I was blushing under the makeup and changed the subject ‘Thank you, but are we stopping here all evening or are you going to take me somewhere?’
‘Oh sorry, yes, going back to my house, drop the car and get a taxi into town, a nice wine bar then maybe a club. How does that sound?’
‘Sounds fine to me.’

A short drive to his house where we meet the taxi he had ordered as we left Beth’s. The wine bar was softly light so I felt safe from noticing eyes. I did my best to make him feel special, I asked him about his life, linked his arm as we walked, though that was as much for support as I controlled my balance on the heels, then as we ate I let my manicured fingers touch his hand and my foot stroke his leg. Beth had done these sorts of things to me and I did them as an act to start with but when I got a reaction from him I did it for another smile or a returned touch. The meal over I was rather enjoying myself in trying to make Marcus feel special he was making me feel special also, I felt comfortable with him, looked after, taken care of, his. And besides how he was making me feel, the clothes were having an effect as well. The soft satin dress fabric riding over my bare buttocks as I walked felt sensuous, the bouncing breasts in my bra reminded me if needed that I had the shape of a woman, and my heels stopped my clomping about like a man and forced me to walk in a different manner which I hoped was with a wiggle as Beth required.

The club Marcus took me to was one with a diverse clientele, every sexual orientation was there I guess so I did not feel threatened or to weird. As I drank my first drink there I saw men kissing openly and two women elsewhere not hiding their lust for one another if where their hands were was anything to go by. I remembered what Beth had told me and put my hand on Marcus’s thigh as he put an arm round my shoulder. Soon we had danced, cuddled and even kissed properly. In the toilet, ladies off course I was about to wash my hands when I noticed the women checking themselves in the mirrors and repairing their makeup, so I followed suit. As I touched up my lipstick a big woman came beside me, looked me up and down, and then in an unusually deep voice for a woman asked ‘You with Marcus?’
‘Yes.’ I replied.
‘He is gay you know.’
In that moment I realized I was being taken for a woman, this person thought I was a woman. Now do I answer ‘Yes I know’ and revel myself, or say ‘Is he?’ so concealing my sex and affirming their belief. I said ‘Is he?’ I rather liked the idea of being taken for a real girl. I could tell I had given a confusing answer so when I found Marcus I made sure I kissed him like I always hoped Beth would kiss me, and in view of my interrogator.

Marcus took my kiss as a turning point he later told me, it had felt as if I was playing a role until then but with that kiss I signaled to him that I had stopped acting and was for real. Before he had chatted with a few people he knew, after that I got his undivided attention and I enjoyed being treated that way, I felt special. Soon it was gone midnight and we were having a slow dance and my mind was flitting between going home and feeling Marcus’s erection pressed against my stomach with the added thought of ‘does he want to stick it in my arse?’ and even in my tipsy state it scared me.

We left the club and made our way to a taxi office nearby, and as our taxi pulled up Marcus asked ‘Mine or yours?’ and though it scared me to think of what might happen if I went back with Marcus, to go back this early to Beth would almost certainly mean I would be house hunting in the morning.
‘Yours’ I replied.
‘Sure?’
‘I think so.’

We had a night cap and some arousing kissing once we were behind closed doors. He kissed cuddled and touched me in such a way that I lost my inhibitions as I thought about how I would just kiss then screw Beth. My next shock was handling his cock and recognizing that compared to mine it was huge or maybe mine was just tiny, after all it was the first erect cock besides mine I had ever seen in the flesh.

He ever so sexily removed my clothes before laying me down on his bed, I was then treated to Marcus doing a strip for me, by the end all I wanted was to see his cock fully exposed. OMG it was as big as I thought, how would that fit inside me? And did I want to know what it felt like inside me? I had come this far, off course I did. I held a hand to him and invited him to join me. Soon he had massaged jelly into my arse pushing his finger inside so I got an idea of what was coming, then with my condom safely slipped over his pole he gently but firmly started to enter me, there was no rush he was savouring the moment. He treated me with respect, if I flinched in pain he stopped and caressed me before pressing further in. I could not believe it when after several slow ins and outs I felt his body press against my buttocks, all that cock was inside me, amazing. Next he slowly started to screw me, pumping as he did something inside me that seemed to inflate, a rising sense of excitement. His pumping increased in rhythm as my excitement grew until I reached out and grabbed his arse pulling him into me, my back arched as I reached bursting point, somewhere a voice was saying ‘go on’ in between moans. And then I came, not a quick sudden rush like I did with Beth but a deep panting as waves of delight flowed through me.

I relaxed, exhausted by my experience. I lay in Marcus’s arms holding me tight feeling wonderful in the post coital euphoria. I had learnt so much in just one evening about how wonderful sex could be, my question was, did I want to go back to Beth and show her what I had learnt or be Marcus’s girlfriend again and enjoy being screwed like a woman. I very much preferred the latter if I was totally honest.