A few years back when I was 30 years old I was sent on a training course in my new job, the course lasted three weeks and took place down in London. At the time I only dressed either for myself or for certain friends who granted me sexual favours. I lodged with an bi sexual ex girlfriend from my teens, Carol who had loved dressing me up in her cloths. So I was able to become my feminine self in the evenings. It was lovely to be all feminine with a full time girl companion do our hair and nails etc and just chat over a nice bottle of Frascatti or 2. I did confide in her when we were doing a facial de tox, that I had freaked out on the course by the fact I was physically attracted to a few guys when I was not fully en femme but wearing my lovely satin lingerie. She said it sounded like the bisexual part of me that she always suspected was there was now coming out when I felt pretty. She said she knew loads of guys who loved tgirls and her boss Henry was always trying to recruit pretty ones like me. She said Vicky your a girl inside and when your dressed like you are now, you dont look like a guy at all, I just laughed, and looking over in her direction covered in cream and cucumbers, my hair in rollers to give it bounce, with my baby doll under my silk robe and my fluffy heels on. I said hey we could be the London equivalent to sex in the city. But as for the guys on course maybe she was right, not knowing how to deal with this situation, I certainly didn't want to talk about it with them, because I knew they would laugh and probably reject me but if I looked girlier and smelt and looked nice, who knows. My friend said that the next time it happened then I should find a way of checking the situation out, also she said I made a very pretty girl more pretty and cute and better as a girl than I looked as a guy. So she said Vicky, express yourself where something feminine you will look lovely and I bet you get approached. Anyhow the course was boring apart from the few hunky guys, even the other girls were a bit stiffy and didn't talk feelings, fashion, celebrity gossip or anything that was usually important. Every morning was the same old routine; out of bed off with my cute pyjamas, shower soap shave everywhere so that I was ultra smooth, check my make up was fully removed, apply some, day cream, slip into my lingerie, check my nails, have a light breakfast, change my robe for the rougher mans attire spray some nice cologne, then walk practicing my poise down to the bus stop, be squashed and lurch about whilst checking out what the girls were wearing, take the Underground, being surrounded by mostly ugly, smelly people. By day three I had been encouraged by my friend to try out the sales on Oxford Road, a few womens shops had 70% off and I was gradually turning myself more and more en femme. One certain day after the course I had waited for everyone to leave and had nipped into the ladies loos and had dressed myself in a deep brown lovely ladies trousers suite that had a light silky flowing feel, underneath was my usual cream suspender belt stockings and silk panties. Up above I wore a simple white silk t-shirt and a loose cream camisole. My boobs were still developing but the nipples did make a nice impression through the sheer material which you could glimpse invitingly through the single buttoned suite jacket. A little medium pink eye shadow, brown mascara and nude lipstick with a light liner looked okay under my waxed streaked blond, pixie, boyish hairstyle which I fluffed out. A nice smart pair of 1.5" dark brown pumps which looked a bit like brogues with two laces, matched my smart brown leather zipped Filofax case. The case had room for makeup etc if you took most of the pages out, and this finished off my tom boy city girl look. I admired myself in the mirror before exiting the loos and stepping into the quite corridor..I was feeling extra lovely and free. My unwanted mens stuff I left in my lockers by the main door. A few swinging step down Oxford Street, moving my ass to the tube felt great and I was getting some looks built my confidence, as did the nice old guy holding open the door for me at the tube. I chatted small talk with him as we were pushed along with the crowds down to the platform. Which I stepped onto smelling off my favourite Chanel 5 perfume and then onto the carriage when it arrived. As usual everywhere was crowded and my boyish feminine attire was lost in the rest of the work weary crowd. The Underground was packed as always, and here I was standing in the middle of one of the carriages my clothes felt lovely on against my smooth legs ad body, and I was enjoying the sensation of getting a couple of looks from some young guys and a very smiling look from a dyke down the carriage. I couldn't help but lick my lips a little and smile at her, she smiled back sweetly. She had nice eyes and a strong looking figure. At least I thought, the 15-minute trip would be for me not as boring as usual. Within moments, I felt a hand brushing up against my ass. At first I thought someone was trying to grab the pole to hold on, until I realized the hand continued to massage my ass cheeks in-between running his fingers along the outline of my suspenders and panties . Being shy, and this having never happened to me before, I didn't turn around to see who it was. Enjoying what was going on, licking my lips at the dyke whilst I was hoping the people around me wouldn't notice what was happening under my silks to my cocklet which was slowly responding to the unknown caress-er. The hand slowly slid to the front of my body and continued its massage inside my leg until it stopped on my upper thigh. I could now see it belonged to a man, it looked tanned and strong with well manicured nails which I like. Continuing to move his hand upward on my thigh, he reached his final destination--my crotch. Massaging my cocklet through the fabric of my pants, my cocklet was now responding to his touch. Instinctively I moved my body closer to his, my ass now rubbing against the bulge in his pants. He put both hands on my hips and pulled me strongly backwards onto his hardening bulge. Simply heaven heaven heaven heaven wonderful heaven it felt divine through my silky trousers and satin panties. His hands moved again and continuing to massage my cocklet through my pants during the Underground ride, this stranger could now feel my entire 6" of hard meat. I started to leak a little oh god no stains I screamed inside please my suite my pretty suite would look awful, Suddenly, he started poking my peachy asshole through the fabric of my pants with his finger, sending electric vibes through my body. I couldn't help but let out a soft moan. I couldn't believe how good this man was making me feel. I wanted to stay all night in the Underground. He was massaging my cock with one hand and pushing a finger in my asshole with the other. I moved slowly swaying with hot pleasures, moaning and licking my soft lips I would have wanted to take my pants off to give him easier access to my body, but since there was a lot of people in the Underground, I couldn't. The attractive manly, dyke was watching me in some amazement and as the train stopped she squeezed past me with a smile pushing a small note into my suite pocket. See you tomorrow she said, loved watching you, my names Bobbie, ring me babe. Sure I said.
The train jerked to a start and the finger pushed inside me further. He had stopped fondling my cocklet and concentrated on my thighs and ass which I preferred. At one point, in a low sexy tone the man whispered in my ear "Youre a pretty thing? Later "I love your ass I'm going to make it mine" " you little minx" "move that ass girl" then" I'm getting off at the next station, follow me." I didn't know what to do. I didn't know this guy. In fact, I couldn't even see his face. However, I was so aroused by the way he was touching me, curiosity got the better of me and I followed him my heels clipping on the platform down to the ticket booth, I smiled sweetly at the old ticket guy who leered sexily at me over touching my hand as he clipped the ticket. Once we got off the Underground, I finally saw my lovers face. He was much older than me, around 55 years old based on the greying highlights in his short light brown hair. "My name is Henry," he said as he pulled me close to him, squeezing my ass cheeks with his firm hands and pulling my head to his with a kiss. He took my hand and led me up the stairs and out of the Underground station. Once we were outside, I was feeling very nervous as I had no idea of what to expect next. Noticing I still had my raging hard-on from the exciting Underground ride, Henry looked at me and asked "What's your name, cutie?" "Vicky ," I responded with a shaky voice. Walking in a park near the Underground station, I was too shy to say anything. Walking by his side nervously holding his hand, I began wondering where he was taking me. He stopped and turned towards me again, reaching out he grasped my neck and pulled me closer to his lips kissing me deeply. "God you smell beautiful girl" He withdrew his kisses his hands massaging my ass and reaching under and through my legs he pulled me upwards powerfully kissing me "Your my little girl" he said holding me around my waist we walked on, Suddenly stopping next to a small cabin where the park employees store the equipment, he managed to get the door open and pulled me inside. As soon as he closed the door he turned and kissed me and whilst our lips met , Henry helped me to slowly take off my clothes. I was so excited at this time; I couldn't believe I was going to get naked in front of a man letting him see my girly-ness and my hard cockle pointing at him. Completely naked now, he got close to me placing his hands on the firm cheeks of my ass. Kissing me hungrily, his tongue pushed deep in my mouth almost choking me. The feeling was unbelievable. As he was kissing me, his hands started sliding over my body quickly moving everywhere his fingers on my nipples and then grabbing my throbbing cock. Slowly stroking my hair pulling me everywhere fingers snatching at my ass while at the same time French kissing me, I was in heaven! I never felt this good in my life. After a few minutes, he stepped back and just looked at me. In a firm, authoritative tone, "take my trousers down undress me." I did as he said, within seconds he was completely naked. Staring at his expanding cock, as long as mine and two times thicker. Putting a hand on his cock and gently stroking it, this was the first time I touched a complete strangers cock for years, Henry put his hands behind my head his fingers twined in my shoulder length hair and guided my mouth onto his hard manhood. "Suck it!" he said pushing my head closer to his cock. I was able to smell his musky, sexual scent. Opening my mouth, this stranger forced his massive cock deep inside. Choking on its thickness, I slowly sucked his cock while swirling my tongue around the tip. "Mmmmm--yessss, Vicky!." Henry was really enjoying this. The more he moaned - the faster I slid my mouth up and down the shaft of his cock. "Oh! Vicky! You are a great Cock sucker! That's it you little pussy? Let me fuck your mouth." I could tell by the sudden jerking of his rock hard cock lodged in my mouth, he was on the verge of cumming. Just when I thought he was going to empty his load, he pulled out of my mouth and pushed me on the floor of the small cabin. "Get on your knees you little slut! I'm going to fuck your girly ass" I did as he instructed. I was a little bit scared because I never had anything put up my ass before. He lubed my asshole, then pushed two fingers deep in my tight hole stretching the opening. While he was finger fucking my ass, I started massaging my cock slowly. Pushing a third finger in my ass, it started to hurt and I let out a loud moan. "Don't worry girl you'll get use to it," Henry remarked. Stroking his tool with his own saliva for lubrication he slipped a condom on and more lube , a few seconds later I felt Henry's thick cock entering my ass--stretching the entrance to it's maximum. I screamed in pain. There were tears running down my cheeks. He forced deeper, then withdrew completely. It gave me an amazing feeling. I continued jacking off. Then without warning, he shoved his fleshy weapon deep in the entrance. God I felt a complete woman, This stranger's length was impaled so deep into me, I felt his swelling balls bouncing on my own sac. With brutal force, Henry was fucking my tight ass. "Oh yess!!! You're my bitch, Vicky! You ass is so tight." I was on the verge of cuming. His hot body was pressed to mine. I could feel beads of sweat trickling down my back as Henry continued pumping me. I couldn't hold it anymore, I felt my orgasm build up inside and in seconds I shot out a huge load of cum forming a pool beneath me. On the verge of cuming himself, the stranger at the last minute slipped out of my hole-turned me around-and slid his slick covered shaft deep inside my mouth. Not having time to react, he spurted a warm load of cum-over my mouth and face. I loved the taste and feeling of this stranger's cream going down my throat. Collapsing on the floor for the next few minutes, I got back to my senses. Looking at me, Henry's final remarks were, "You're a good bitch, Vicky . Maybe we'll meet again tomorrow in the Underground." Smiling at me as he got dressed, the stranger stepped out of the cabin leaving me completely naked lying in my own cum and covered in his. I dressed slowly feeling so much the woman who had pleased her man. I walked slowly feeling good and reliving the way his dick had entered me.
I had to retake the underground one more stop with lube in my ass and a slight stain on my suite. I had minced up to the ticket guy still tasting Henrys cum, the guy could smell me, a mix of expensive perfume and cum and gave me a smile and squeeze on my ass as I walked past, I wanted to miss the little freak but instead I decided I was a smart city girl who loved casual sex and not a prostitute, so I just turned and blew him a kiss before swinging my hips down the platform to the ladies loo so I could fix myself with a stronger shade of lipstick and now that I was confident with black mascara, I read Bobbies note and thought it fun to date her and rang when I got off the tube. She sounded lovely and so dominant that I arranged to meet her the following day for lunch. Tomorrow, I would wear my new suite to the course, with just a little make up I decided. Vic becomes Vicky. When I got back home, having re lived and re loved every divine moment on the train my ex girlfriend Carol told me to sit down she had a confession to make, she had conspired with her ex boss, to be on the same tube, he had followed me on to the platform, but she said the good news is my boss Henry rang to say he met you as we had planned on the train. He told me to tell you, she said that you’re a hot minx. Vicky she said he wants to invite you to interview which would mean staying on in London as his secretary.
We dressed ourselves in our best sexiest clothes, I rang Bobbie and asked if she was out tonight and we arranged to meet up there and then and the three of us went out to celebrate as best friends do lapping up the looks of the guys and having some flirt fun.
story by
MissVictoria Bobbie Miller
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