Tammy
It was obvious from the second that Tammy walked in the door that she was different, she looked cute, innocent nicely dressed and scared. She had applied for a job with my Marketing company and event from the initial phone conversation that she was nervous, but she was intelligent and keen to learn, and damn it if I didn't feel my cock begin to rise against my will power as we spoke. She was 18, just over 5 feet tall, skinny with dirty blonde hair and bluish grey eyes. She wore a nice loose blouse with a neck scarf and a short grey skirt with black stockings and modest heels.
I interviewed her and she did very well once we got chatting, she started to make eye contact which began to border on flirting, I knew I was going to give her the job right there but I couldn't tell her as I had already said there where others to see. I was sorry to see her leave and as she went through the office door she looked back and smiled. As soon as she had left I locked the door and took my raging cock out and started to stroke it as I lay back in my office. I wanted her so bad, I wanted to feel her little tits and have her lick my cock and balls spreading her lipstick all over it. Gosh I came faster than I had in years I am in my 50's and the thought of touching such a young sexy thing was like winning the lottery. I went back over her application form, she had identified as female. But I had my doubts, there was something about that sexy walk that suggested I might get a surprise. Later on I phoned her and told her to start Monday, I couldn't wait and she assured me she couldn't either.
Monday came and she was at the office before me, standing outside and obviously freezing. She had a pale yellow blouse on with no scarf and a different darker grey skirt, and dark blue stockings with a lovely pattern on, she certainly knew how I like my girls. She made me a cup of tea, a bit on the weak side and seemed to be practising her bum wiggle as she walked through the door. I got my IT guy to set her an email account up and show her the back office system until I got through my emails, then I joined her after lunch and went through how we contacted clients and put the deals together. I was sat next to her on the office chairs and as she typed I couldn't help but to savour her perfume, quite delicate just like her. I sneaked a look down the top of her blouse, she had a light blue bra on, probably an 'a' cup with delicate little lacy patterning all around it, her blouse was loose enough that I could see the shape of the bra cup, her legs looked skinny and long which was exactly what was happening right now to my cock. I wanted to bend her over that computer desk and mercilessly fuck her. God I could be up for a tribunal at this rate!
I got called away luckily, and later on my IT guy had to go to visit a customer some distance away. I joined Tammy about 4 o'clock and we where the only people in the building. I was trying to focus on the work but somehow beyond my control I heard myself say, 'Tammy you are very attractive', then I gulped and was about to pull back when she turned to face me and looked into my eyes and licked her lips seductively and said, 'Thanks but I am not like other girls and I really like working here so far'. I started to splutter and explain that she could work here even if she rejected me and I caressed her shoulder and her long straight hair and she turned slowly and I felt our faces love closer and we kissed so gently at first. My hands either side of her face, her skin was unbelievably soft and I now had an uncontrollable erection, I massaged her back then I thought what the hell and moved my hands to her breasts and squeezed and realised that she did not actually fill her bra, it felt like cotton wool but there where little breasts in there for sure. Her head went back and her mouth opened as she groaned. I felt her hand slide up my leg and firmly grab my cock. I undid her blouse as she stroked me. Then she kissed me forcefully and gasped as she undid my trousers, 'you have no idea how much I need this!' and she grabbed my cock breathing deeply. I eased her blouse off and I could feel her shaking as I caressed her bra straps and eased them off her shoulders. 'I am so sorry Ian but there isn't much in there', she looked close to tears. I brushed her cheeks and kissed her eyes and said, 'It really doesn't matter, whatever you have is what I want, believe me I haven't stopped thinking about you since you tripped over the doorstep'. She laughed and I worked her bra straps over her shoulders. Sure enough the little light blue bra was padded with cotton wool and as it fell away, there they where, two very small breasts like half tennis balls with quite large bright pink nipples which where standing to attention. She was exploring my cock and balls, she had quite a grip. I pushed her back on the chair and started to kiss and suck those pretty nipples, she squealed with such delight that I thought at first that I had hurt her. My hands worked down her slender body and glided up her thighs. I could feel her trying to pull away, what was the problem? She was still gasping, 'Are you a virgin?', I enquired. 'Well sort of', she whispered and as I got her skirt up and saw her pretty lacy French knickers sticking up in a little bulge. I could see tears run down her cheeks. 'It's OK baby, I could not want you any more if I tried'. I kissed her tears away and caressed the erect little cock that was sticking up in her panties against her tummy. It was about 4 inches long and not so thick, not that I am massive myself at 6 inches.
I pulled the top of her panties and there was an exposed glans sticking out of her foreskin, all wet and slimy, Tammy calmed down and I started to lick the end of her little cock. I had never touched another cock but when I was young I had seen two guys at school wanking each other off, to be honest I was really embarrassed at seeing them, but I was always curious about what it felt like. (S)he tasted lovely and as I got more of her in my mouth she breathed, 'no one has ever touched me there before, but I have pleasured men orally'. I re-arranged her cock through the panties leg and pulled her small ball sac through. She was totally bald, I don't mean shaven, it was like she had never grown any hair there. I got the feeling she was going to cum very soon and this was something I had not planned on. I had read stories about what a man's cum tasted like and how some people loved it and some hated it, I wasn't too keen on my own when I tried it,
She pushed me away, 'no not yet!, swap places please Ian', she said so I sat in the chair and lay back. She took my cock in both her small hands and gently wanked me. Then she rubbed it against her cheeks one after the other. Then licked the very tip and grinned, her eyes looking deeply into mine as she spread my juice over her lips then rubbed my cock against them teasing. Then I felt her tongue on my balls pressing deep between the testicles, 'WOW, I gasped, you really are amazing. I don't know how much longer I can hold on'. Then she put both hands on my cock one above the other and fed it into her mouth, sucking hard. Moving her hands away as she took more and more into her soft warm mouth. Then she moved her head up and down on my hard, squeezing my balls and stroking my inner thighs. I could take no more and exploded trying to grab her head but she was going nowhere but down on me. I had what was probably the most powerful cum I have had in years. She gulped and gulped until she had all of my cum down her throat.
While I got my breath she cam and sat on my knee and stroked my face kissing me and stroking my cock. 'I never got used to being in a boys body', she said, 'When I was at school I let my hair get long and boys wanted me to suck them, even the straight ones. I have only just started hormone therapy so my tits will get a bit larger then I'll have to decide if I want implants and save up for them'. I started feeling her cock again and she stood up, her legs shaking. I pulled her panties down and placed my hands on her sexy smooth little arse. It felt soft and inviting, I took her cock into my mouth and started to suck harder and harder, her thighs moving faster and faster, in the space of less than a minute she squirted warm slim juices into my mouth. I felt good, no it felt absolutely fucking amazing, the way her cock throbbed, swelled up just before she came then pulsed 5 or 6 times, even her balls where throbbing in my left hand. I realised that somehow I had worked my finger up her arse about 3 inches and slowly pulled it out. This was something a girl had done to me many years ago and I loved it, Tammy seemed to as well. 'Oh Ian, I have been wanked before but never sucked off. That was truly delicious'. I stood up to kiss her and we embraced each other gently like two lovers, I decided I wanted to do more than just have sex with her, I never wanted to let her go again.
She started stroking my cock which was three quarters hard, soon it was fully hard. 'Would you like to fuck me Ian', she said between kisses. I thought for a millisecond, I had fucked girls up the arse before so why not Tammy. I said, 'When I was interviewing you I visualised you standing up with your hands either side of the desk. She obliged me and I got on my knees and felt and kissed her girlish little arse, then licked her hole as I did not normally keep lube handy, memo to self: order lube. Then she said, 'OK now please! Fuck me! Take my virginity!'. I stood up and eased my cock into her gently and them grabbed her tits and she turned her head to kiss me. It felt amazing, her little 5 foot body precariously balanced on 4 inch heels, felt as good as any woman I have had the delight of bedding. She was very vocal and telling me how deep to go, how good it felt and how she wanted it harder and deeper.
I was feeling her tits and stroking her cock frantically, there was nothing else in my existence at that moment just me and Tammy fucking in my office. She sensed I was close, 'Oh god yes, please please cum inside me. I need this so badly baby. Fill me with your hot sperm!'. There was sweat running down my chest and back, I was banging this little cutie as hard as I could and sure enough I came, came like I had never cum before in my life. My sweat running all over her back, her lipstick smeared all over her face. I shot my spunk into her tight little arse over and over, she squealed so loud and I felt a stream of spunk squirt into my hand which I promptly rubbed all over her cock. This was the best fuck of my life no mistake.
As I pulled out of her my mobile rang, damn it, I hadn't got my breath back yet. It was Ed my IT guy, he told me he had fixed the client up and would see me tomorrow, he could tell there was something going in because he was hesitant when he heard my voice. 15 seconds later I got a text message, 'Hope you are fucking that hot little filly!' I sure am I thought and showed Tammy, she giggled and we collapsed in each other arms and fell asleep.
We left work about 8pm and went to a restaurant nearby and got a a much needed drink and ordered food. Tammy told me she had felt my eyes on her during the interview and wanted me whether she got the job or not. I told her I had just broken every rule in the book and was glad she had responded or I could be in so much trouble. She said that since she started the hormone treatment she looked a lot more girlish in the face due to starting it young, at 16 , which you can't do in UK but her parents where in Thailand when she was growing up and she learned from all the Ladyboy's, She said she didn't plan to have the full operation unless I wanted her to. I told her that after what we had just done I did not think it would get any better but then I never thought I would be fucking a transsexual. In fact I was pretty sure I was falling in love with her.