I was standing there and feeling nervous, not sure how he would react when he saw me. I was in his house and I hoped he remembered giving me his key on Monday, four days ago. I saw his car pull up outside, and I quickly slipped on my heels, and looked at myself in his mirror. I felt great, confident, so I slipped the short satin robe off, leaving it on the sofa. Another quick look at the victoria secrets lingerie I was wearing, the thong showing my bum, the stockings, my cleavage and I walked over to stand in his hallway, looking at the door as he put the key in, hands on my hips, one leg thrust slightly in front of the other. The door opened and Mike looked at me, his jaw dropping. Yes, I felt great, and looked as good as I could. Then I saw someone behind him, who stepped forward……..
It all started two months ago, just after the end of January. I work from home as a copywriter, and I’d just completed a eight week job in four, something I normally wouldn’t do as I only work to give myself something to do. I have no family anymore, my own home which all paid for and money in the bank. All my friends have moved away after university, my girlfriend split up with me months ago, and the four weeks work had taken their toll on me, and my laundry basket. I’d run out of clean clothes and resorted to what my ex had left behind. It wasn’t a big deal, I’m very androgynous, something my ex loved and she would often encourage me to dress up for her, and sometimes when we were out, she would get me to pretend to be a girl to get us free drinks. It was funny, and the sex was usually great when it happened, so it had its upside, and more than made up for the annoyance I used to feel when I was younger.
So here I was at 11pm, uploading the work and drinking some wine to celebrate, wearing a pair of her panties, leggings and a red roll neck sweater of hers, feeling very happy. As it finished and I hit send, I realised I’d drank half the bottle, so went to the loo, pulled the leggings and pants down as I sat to pee, wiped and pulled them back up, giggling to myself at peeing like a girl. I went back to my PC, printed out my worksheet, and stuck it in an envelope with a stamp on it. I’d already emailed it, but this was the signed version for the records. I looked at what I was wearing before heading to the letterbox, and decided to pull on the Uggs to go with the leggings, looked at myself in the mirror and thought sod it, I need to do laundry tomorrow, so why not have some fun right now?
I went back upstairs and looked at the clothes that were left in my spare room, and took the leggings off, and picked up a pair of tights, saw they were laddered, found a pair of hold ups and slipped them on. Next was a bra, then a search for the chicken fillets to put in them. Back went the sweater, then I looked for a skirt, and I found a black wet look skater skirt that she loved me wearing. I looked at my hair, and although it was longish for a guy, it just looked wrong so I slipped floppy flat hat on and decided it was ok. I only need to shave once a week, and even then it’s not very much and quite fluffy, it goes with me being skinny and androgynous thanks to a Chinese grandparent. I looked around for some shoes and found a pair of ankle boots with 3 inch heels, and slipped them on, going downstairs carefully thanks to the wine. It was dark and cold out, so I grabbed one of my hoody jackets, put my keys in my pockets and walked to the door, grabbing a drink of wine on my way out. If it hadn’t been dark, a very short walk and the wine, I wouldn’t have done this. I walked the ten metres to the corner, turned and walked another 20 to the letterbox by the shops, loving the sound of the heels clipping as I walked. I posted the timesheet, turned around and fell over.
“Are you ok Miss?” A voice said. I looked up and a man I recognised was looking at me. He lived around the corner from me, technically my next door but one neighbour, but as we don’t live on the same street, I only know him by sight. I tried to stand up and realised he could see up my skirt, and I tried to sort it as I started to stand up. He had come over to help me, and took my arm, I could hardly say no. As I put some weight on my feet, my ankle felt a bit sore, and I said I’m ok as I looked at him. He recognised me as well. “Um hi, sorry about this. I’d had a little to drink and thought it would be fun.” I told him as I looked up into his eyes, even with my heels and being 5’9”, he was still taller than me. He asked if I was ok to walk home which made me giggle a bit seeing how close we both knew it was, and he said, “Look, I know it’s not far, but come in and sit down for a bit, let yourself sober a bit before you walk home.”
I looked at him, and nodded, really just wanting to go and hide, but I sensed he wanted to ask questions and this way I could just it over and done with, so he helped me to his door and we went in. I sat on his sofa, smoothing my skirt out as I did and crossing my legs to hide my panties, as he went to make some coffee, wondering what I would say, but decided the truth is always the best option. He sat down and asked how I felt as I took a sip of the coffee, explaining that I’d been working flat out for four weeks, and was having a laundry crisis, so just dug into my ex’s clothes. I also explained a bit about how she would get me to dress up for her sometimes seeing that I’m slim and often mistaken for a girl. I said to him, “I hope you don’t think I’m weird”. He replied “No, it’s ok, if anything I was a little upset as I felt like I was coming to your rescue”. I laughed and said he did. We talked for about an hour, and I admitted that being single now for six months and feeling lonely, the drink and work, then the clothes and going out for the short walk felt great, almost as if I was a different person.
“So if you feel good, do it as much as you want.” He said. I told him I feel embarrassed sitting here with him, and beside, I don’t really look good enough, my ex used to do my make up and all I could do was touch it up. “Besides, there’s not really a lot of clothes left behind.” I said. He looked at me and made an offer that really surprised me, he said, “Look, if you want to do this and feel safe, then put some items in a bag, come round here and dress. Then at least you’re not sitting there by yourself.” I said I would think about it, but he said ‘no, just do it’, and I agreed to go round his after he finished work tomorrow, dress and have a take away with him.
The next few weeks were quiet work wise for me, so I had nothing to worry about but going food shopping and watching Netflix, so every other day, I would put some clothes in a bag, go to Mike’s, and we’d chat, have a take away and watch a film on TV. During the day, I was working on learning how to improve my make up skills, buying make up and some more clothes online. As I got more confident, I would do my make up before going to his, it was dark so I wasn’t worried about anyone seeing me with a baseball cap on. I’d brought a wig, a real hair one that was really expensive and allowed me to style it a bit, and now I would model the clothes that I’d brought to show them off. The compliments were always appreciated, both the verbal ones and the looks he would sometimes give me; and sometimes I would see he had a bit of a bulge too, so that’s a compliment, right? I also learnt how to tuck, allowing me to wear tighter skirts.
It was while wearing a bandage skirt with a pair of suspender tights (which I love), and a pair of knee high boots with a two inch heel on a Friday night that he looked at me and said it’s time. ‘Time for what?” I asked. Time to go out he said, and he handed me my hang bag. I was confused, “What do you mean?” He looked at me and said, “Look, you look amazing, no one will know, so lets go out for a drink.” I was really nervous, but also really wanted to try this, so I set three rules; first we had to go further away to the next town, secondly if I said I saw someone I know, we had to leave, thirdly, I couldn’t think of a third. He laughed and grabbed his coat, making me realise I didn’t have one. He surprised me by picking a woman’s coat off the peg and handing it to me. I didn’t understand why he had one, and he said, “I ordered this two weeks ago, and left it there for you. You walk past it and never see it.” He held it out for me to slip into and it was a little large at size 12 (uk sizes), but a good enough fit to not worry me too much.
Just as we were about to leave, I stopped him, went up to his spare room, put my clothes and make up back in my bag and brought it down, saying we should drop this at mine, so I walked to my door with him, went in and just dropped the bag, and went to his car. Getting in it with a short tight skirt was new to me, but I quickly worked out to sit in, then swing my legs in, and thinking I should have worn a different skirt, this looked really short sitting down. We drove to the next town about 30 miles away. It was a Thursday so it was fairly quiet, but we found a bar near the waterfront, had a couple of drinks and a visit to the ladies for me, then we went back. Literally nothing happened, no one pointed at me, I felt normal and looked normal. We even held hands as we walked in and out of the bar. It was about half ten when we got back, not late, but it wasn’t a work night for me, but a perfect end to the week and this whole thing if I never got the chance to do it again. I knew Mike was seeing people from work tomorrow and Saturday, but we agreed to do the same on Sunday. I told him I would wear jeans then, as it would make more sense and he laughed saying, “You’re turning completely into a girl if you’re planning outfits already.” I gave him a look, but did laugh at it, I was planning everything I was going to wear.
He walked me to my door, and surprisingly we were holding hands again for the short walk. We looked at each other and he told me how much he enjoyed spending time with me tonight, and he’s looking forward to Sunday now. I smiled and told him I was as well, and he leant forward and gave me a quick kiss on the lips. He didn’t look embarrassed about it, and it seemed like the perfect end to the night. I smiled at him and said I’d see him Sunday, and to text me when he was awake so I could come round. I went in and went to bed, enjoying the slow act of stripping my clothes off, and got into bed, naked. I then got back up to take off the make up, I’d learnt my lesson on that.
I didn’t hear from Mike until Sunday, but I wasn’t expecting to, but it gave me a chance to catch up on my paperwork, and do some food shopping, and a little bit of work that had come in. Sunday morning, I woke up to a text from Mike, asking what time I was coming round. I replied saying at 3pm and I did a bit of work. I was thinking what to wear and jumped in the shower and tucked with the new method I’d tried yesterday and it worked really well using a bit of spirit gum to hold everything back in place. When I started to get my bag ready, I changed my mind. It was a short walk, and I could do it and it would be dark soon anyway. I slipped on a bra and thong, my new skinny jeans, a jumper which was so soft it was unbelievable and my wig. I did my make up and realised I only knew how to do a nighttime look, but with no time to learn anything new, it would have to do. I slipped on the ankle boots, then clipped on my hoop earrings, picked up my handbag and walked out the door for the short walk to Mike’s.
He opened the door and said nothing, just looked me up and down. “Well, can I come in?” Yes, of course, he stammered as he let me in. I could see him checking out my bum in the jeans in his mirror, and then he had a little adjust. Ok, this is new, I thought, normally he only gets an erection when I’m showing a lot of leg, so I’m definitely doing something right. We sat around for about an hour as he caught me up on his weekend, then said lets go out, so we jumped in his car, and again drove to the next town. The bar was a bit busier, and jeans were the right choice for me. Again we held hands, but this time he was much more touchy with me, and I have to admit I did tease him. I’d done it before when I knew he had an erection, but this time I wanted it to happen in public, I kept making sure my legs were touching his, I would put my hands on his legs while talking to him, and yes, he was hard.
It seemed like time went faster as we had to leave and I just wanted to keep teasing him. We walked back to his car holding hands, and drove back in silence. I was worried I might have lost a friend by trying to give him an erection in public. It was a silly thing to do, but the validation I got from it couldn’t be measured, it made me feel wanted for the first time in a while, even if it was by a man. He walked me to my door and then really surprised me. He turned me round and kissed me, full of passion, his hands running over me, and I pressed against him as I kissed him back. I hadn’t realised till that moment that I wanted to be kissed, I wanted to feel his hands on me. I wanted him. He broke off the kiss and looked at me, and all I could feel was the heat from his erection pressing against me. “I need to go home.” He said. I replied, “I know.” And kissed him again, and we just carried on kissing. I’ve no idea how long it lasted, but it could have been a minute, it could have been a year, I just know it was good, but he did leave to go home, and I went in, stripped of and went to bed wearing nothing but a smile.
In the morning I woke up to my phone ringing, and knocking at me door. I stumbled downstairs wearing a robe and Mike was there. He apologised and said he had to go away for work, he just got called and wouldn’t be back till Friday night but hoped we could go out again, maybe for a meal. I said yes without hesitation, and then he handed me his door key and said he was having some work done on his fence and I might need to let them in if his landlord didn’t. This surprised me as we shared part of a fence, but I thought nothing of it other than that. Then he gave me a quick kiss on the cheek and said ‘text me’. I brushed my cheek and realised I was still wearing the wig and my hair was a mess.
I didn’t have any work to do, so after a lazy breakfast and shower, I sat down to do some more youtube make up tutorials, determined to learn how to do a daytime look. One of the suggested videos when I was looking at how to style my wig was for using hair extensions. It didn’t look easy, but I ordered some for next day delivery, and then just chilled out in my robe all day having a Netflix marathon. The next day, the hair extensions came, I spent the day learning how to clip them in, and trying different make up looks, and again the day after, including how to enhance my cleavage using makeup, with the new stick on bra to pull them up and together. It wasn’t the most comfortable, but the results were worth it. On Thursday morning, I did the day look and hair extensions together, and was really happy with how I looked, so I slipped on a pair of suspender tights, an A line button up denim skirt, roll neck jumper and a pair of Uggs, feeling really happy with my look. I’d been texting Mike through the week, and been teasing him with pics of what I was wearing each day and today I sent a pic of my stocking tops. He replied really quickly saying “Jesus, are you trying to make me hard? I’m trying to focus here!” OK, I thought, in that case I’ll send another. He replied me the eggplant and redface emoji. I replied, “Show me the bulge”, and a few seconds later a pic came through of his suit trousers, with a bulge in them. I replied, I’ll see you tomorrow.
Then there was a knock on my door and I remembered it was Thursday, the men were coming to fix his fence. I walked to the door and opened it, feeling very nervous. I’d been practising my female voice, and this was my first real test. “Hello love, we’re doing the fence and the landlord has let us in, but just to let you know we’ll be in the bottom of your garden as we put it up. Is that ok?” For a minute, I wasn’t sure what to say, and just said it’s fine, not a problem. They said thanks and looked me up and down as I closed the door. I’d passed for a girl up close and there were no problems. Ten minutes later I look out back and they had taken the fence down and were working away, and I thought sod it, lets do it. I opened the door and walked out, offering them a cup of tea. They both said yes so I told them to come inside in five minutes when it was done. Five minutes later, two workmen were standing in my kitchen, holding mugs of tea and eating biscuits as we chatted about nothing in particular. I did smile to myself as I thought this is like a bad porno, but I had no intention of doing anything. I did tease Mike by telling him I had two burly workmen in my kitchen, but really, they weren’t very good looking. By now my confidence levels were really high, so I said I was just popping to the shops to get some milk and did they want anything? They were fine, but I changed my boots in front of them into the knee highs, making sure they could see my stocking tops as I did so. I didn’t want to go to the shops near Mike’s as I always go there, I turned left and walked along my street. My hair felt great, so much nicer than the wig, and walked a bit further than I needed to. In the shop, no one paid any unusual attention to me, I brought some milk, a couple of women’s magazines, and went back to the workmen. I was surprised when I got back that they were just putting the last panel in, so I told them to come round the front for some tea and toast before they left.
Chatting to them up close, and the walk to the shops made me almost feel invincible, but I knew I still had to be careful, but after they left, I made the decision to go shopping. I slipped my coat on, grabbed my bag and went before I changed my mind, heading for the tube station to go into town. The tube was busier than I expected and I couldn’t get a seat so I stood, then decided to go to oxford street. I wanted to buy a dress, but ended up buying two, and a couple of skirts and tops, a pair of 4 inch heels, and a really cute black trench coat that flared out at the waist and came halfway to my knees. The most surprising bit, I went into Victoria’s Secrets and brought two sets of lingerie, trying them on in the changing room. The journey back was in rush hour, which with my bags was horrible, I should have thought this through better. I also experienced something that many women go through on the tube, and that was the unwelcome attention. I didn’t realise at first, but the man behind me was rubbing himself against me, and then I realised it was his erection, pushing against my bum. I really didn’t know what to do, but the train thinned out the further we got from the city and he moved away, but not before I felt his hand run up my leg and stroke my bum under my skirt. I couldn’t work out if I should be flattered or appalled, and on the walk home from the station, I settled on appalled.
The next day, after working in the morning, I spent the afternoon getting ready for Mike. I didn’t want to text him at all today, I wanted to surprise him, so after having a bubble bath and moisturising, making sure my tuck was good, then after putting on the new VS lingerie, I did my hair and make up, enhancing my cleavage. It was four o’clock and I knew Mike would be home anytime from about five, so I slipped on my satin robe, the heels and the trench coat over the top, picked up my handbag and walked to his door. I let myself in, opened a bottle of wine and poured myself a small glass, as I settled down to wait for his car to pull up outside. I saw his car pull up outside, and I quickly slipped on my heels, and looked at myself in his mirror. I felt great, confident, so I slipped the short satin robe off, leaving it on the chair. Another quick look at the victoria secrets lingerie I was wearing, the thong showing my bum, the stockings, my cleavage and I walked over to stand in his hallway, looking at the door as he put the key in, hands on my hips, one leg thrust slightly in front of the other. The door opened and Mike looked at me, his jaw dropping. Yes, I felt great, and looked as good as I could. Then I saw someone behind him, who stepped forward and said, “Hello, you must be the girl that’s been distracting Mike all week. I’m John, his boss.”
I’m standing there wearing almost nothing in front of a stranger, shocked and wanting to run, but after a few seconds, decided to just brazen it out. I walked over in my most sexy walk possible and kissed Mike, full on and passionate as possible while John closed the door. I broke the kiss off, and Mike’s hand was on my bum, which I realised was pointing at John, so I turned my head and he was looking. “Hi John. I should cover up, but you’ve seen everything now. I should explain, tonight was to be our forth date.” and I gave a little shrug as if to say, hey, we’re in the honeymoon period where we just shag all the time. Mike explained that John had lost his keys and his fiancé is away tonight so he offered his spare room. I gave Mike another quick kiss and told them both to go sit down and I’d get them a drink. When I waked back in with a glass of wine for each of them. Both were sitting on the sofa and my robe was over the chair, so they probably expected me to sit there. In stead, I sat between them. When I topped up my wine, I did put the robe on, but I only tied it loosely so it was constantly open and we ordered a take away, which I collected as I was feeling fabulous. They both thought it was funny that I hadn’t checked my messages saying that Mike was bringing someone home tonight, although I did see they both had a bulge in their trousers when I told them I walked here wearing just a coat, and would have to go home tomorrow wearing the same.
About ten pm, John said he was tired so was going to get some sleep and he headed up to the spare room. I looked at Mike and never gave him a chance to say anything, I just kissed him, and he had a little session there on the sofa. Come on I said, “let’s go to bed”. We walked up the stairs and John came out of the bathroom, gave Mike a wink and closed the door to the spare room. I walked Mike into his bedroom, and sat on his bed to slip of my heels. Mike was nervous and slowly taking off his clothes, so I went to him, gave him a kiss and told him not to worry, nothing was going to happen, we’re just going to sleep in the same bed together. He started to undress, but only went as far as his boxers then turned around. I was laying in his bed, with the covers pulled back showing me laying there in my lingerie, looking at him. He walked over and was trying to hide his erection, so I reached out and took his hands, telling him not to worry. He sat on the bed and laid down with his back to me. He must have been as nervous as me, but unlike me, I’d been wearing this all night. I rubbed my still stocking covered leg on his and told him to turn round, and he did. I gave him a kiss and now he seemed less sure of himself.
“Is everything ok?” I asked. “Yes, well, no. I mean I’m not sure.” He replied and fidgeted a bit. I took his hand and put it on my hip, and told him to relax, this was new to me as well, but we can still enjoy this together. I kissed him and he moved away. “What’s up?” I was worried, but he smiled, “It’s ok, I’m just not used to wearing anything in bed.” I raised one eyebrow at him and said, “Well then….” And I reached out and started to pull them down with just one hand, doing it slowly, and trying to make it last as long as possible. I could feel they were caught on something, and it’s not like I didn’t know what. Finally it sprang free and the relief on his face when it did was obvious, I had been pulling it down with his boxers to tease him more. He kicked them down his legs and out of the bed, and I shuffled closer to kiss him, feeling the tip of his penis touch my stomach, feeling the precum leave a trail there. I put my hand down and wrapped it around the shaft, playing with it and kissing him, his hands were all over me and I moaned as I stroked him.
“You feel amazing.” I told him. He pulled me to him and I could tell he was close to cumming. I let him roll me onto my back and he was above me as I stoked his cock and he came, his seed splashing on my stomach. I wrapped my arms around him, my legs opening as he rubbed his hard cock against my stomach as he kept cumming. Finally he stopped and rolled off me, our arms and legs wrapping around each other as we drifted to sleep.
In the morning, I woke first, went to the bathroom and sat to pee. My stockings were a mess, my make up was everywhere, my hair wasn’t too bad though, so swings and roundabouts. As I was just finishing, the door opened and John stood there in his Calvin’s with an early morning erection. He was in the bathroom with the door closed long before he realised I was there. He put his hand in his shorts and started to pull it out, obviously about to have a wank. I took some paper to wipe myself and said morning just as he took it out. “Do you need this as well?” I asked him. He froze with his erection pointing at me, not knowing what to do. “Now you know how I felt yesterday”, I said as I pulled my thong up. I gave him a kiss on the cheek, and wrapped my hand around his dick, whispering in his ear, “our secret.” I gave him a hand job.
After I cleaned my hands I went back to Mike, he was still asleep, but he also had a morning glory, so I got under the sheets, and snuggled up to him, stroking it. He moaned slightly and rolled onto his back. I kissed down his body, wanting to have a look it. Mike was bigger than John, and I wanted to get to know it better. I kissed the tip. Ok, not bad, so I kissed the shaft, and that was ok. I licked it. Still not having a problem, so I kissed the head again, then licked it. Finally I was ready and I opened my mouth and sucked him in. He moaned again and then his eyes opened, and slowly a smile formed on his face, as I sucked away, enjoying the feeling of him in my mouth, my hands. I worked the shaft with both my hand and mouth, luxuriating in the silky smoothness, the hardness within the soft skin as I worked him. He started to breath faster and it felt like it was growing in my mouth then he came, filling my mouth with his cum. It was hot, hotter than I expected and I struggled to swallow it while he was still in my mouth, but you’ll be pleased to know I managed it. I licked him clean, then told him to have a shower, breakfast is in ten minutes. I slipped on my robe and headed down to make some coffee.
Half an hour later, in front of Mike and John, I slipped my robe off and put my coat on. The stockings were in the bin, but I considered their sacrifice worth it to how I felt. My make up had been repaired and I was only wearing bra, panties and my coat. I looked at both of them in the kitchen and as a tease I turned round and I slowly bent down at the waist to pick up my bag, showing them my bum. I looked at them both and giggled, “I’m sorry, I couldn’t resist it.” I went over to kiss Mike and gave John a peck on the cheek. John said, “I really hope you come to the work do next weekend, but please, wear some clothes.” I looked at Mike and his eyes said ‘do you want to?’ I told John of course I will wear clothes, but now I need to go home to get some, and I put my hands under my coat, and slowly lowered my thong, stepped out of it, and dropped them in Mikes laundry basket. My own precum had left it’s mark, and my tuck was doing its job. Another quick kiss for Mike, and I walked out. As I walked the short distance home with no knickers on, feeling the air move around me and the fear that a gust of wind would catch the coat, I thought about the last thing I heard as I shut the door, John asking where Mike found me.
To Be Continued......
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