My story is nothing new, like most girls who used to be boys I knew from an early age that I was different to all my school friends. My dad was a thug of a man, who enjoyed the physical battle of the rugby pitch as much as the post match booze up, but I took after the mother who died giving birth to me. Oh tried to be the sort of little boy my dad wanted, but being small and lightly built I was never going to captain England in the six nations, or be the strapping chip off the old block he wanted. He was very much a man's man, while I from about as far back as I can remember I used to go to sleep at night wishing I would wake up next morning as a girl!
Puberty was for me a very unpleasant happening. While all my friends became inordinately excited by girls I was finding myself fantasising about boys! They say your school years are the best in your life, but that was not my experience, because for me it was hell. Looking back at those years now all I can recall is having the shit kicked out of me, but somehow I survived and even managed to leave with a few qualifications to my name! Confused and twisted up about being clearly male, yet feeling like I should have been a girl I shocked everybody and did what my dad wanted and joined the Para's! I felt sure that if anything could cure me of my feminine urges it was the Army. No longer would I fantasise being a pretty girl in the arms of her boyfriend, the Para's would make me a man!
Basic training was putting it simply hell, but like school I survived it and when I got my red beret and stitched my jump wings on my uniform for the first time in my life I felt proud of myself. I spent five good years in the Para's, but even after seeing combat in Afghanistan and Iraq army life did nothing to dent my child dreams of femininity or my conflicted gender and sexuality issues. Completing my enlistment as a platoon sergeant, I left the military for a university degree course paid for by her majesty.
I liked University life although after the forces it was a very different lifestyle, and it did not take long for student life to tell on my body. When I left the para's I was a sold 14 stone of shaven headed hardened muscle, with a pocket sized Charles Atlas physique and the fitness levels of an Olympic athlete, but with in a year I was still very fit, but down to a shade over ten stone, with hair past my shoulders. Spending the summers working with deprived kids, I went back for my final year seriously considering doing a PGCE when I graduated, and going into teaching, until I got talking to Andy and at very much the wrong time. I had just got a letter from a mate in Iraq, telling me that my two best mates since basic training had been killed in Basra, and I was raising a glass or six in their memory when we got talking.
I had seen him in the pub before and knew he gay, as he made no secret of it. Anyway I was sat at the bar intent on getting hammered when he walked in alone and recognising me he joined me at the bar and said hello. Reading something in my face he asked if I was okay and before I knew it we were chatting, or rather he was. If I had not had quite so much to drink I would have realised he was trying to chat me up, and although he did slow things right down few minutes after I told him that I was an ex-para once he realised I was not going to plant him he stepped things up a gear.
Oer the next week or so Andy carefully sounded me out and although it was nothing overt, he was clearly getting more and more confident in my company, and began to invaded my personal space. Ever since I left the Para's my long restrained desires to be a girl had been getting stronger, but until I met Andy my main outlet was wearing women's underwear and hanging in tranny chat rooms on my PC.
We had been meeting over a couple of drinks for a week or so, and one evening sat at a quiet table in the shadows of the bar I asked him blushing a little. "Erm look Andy, this is all kind of strange for me, but can I ask you a question?"
"Shoot!" He grinned.
"Um are you trying to chat me up?"
I could see my question had surprised him but he still said looking me straight in the eyes. "Er, well, yeah I am." Andy said gently. "You are with out doubt the cutest thing I've seen in an age and would like to see where things go?"
Oh shit! I thought, "Now what?" I'm not gay, but he was great company and I knew I wanted to spend more time with him. But how?
Seeing that he had embarrassed me Andy again backed off, until we got on to women when he joked that the only sort of girlfriend of interest to him would be a shemale one! He must have read my face because he laughed and said, toasting me with his beer, "You like 'em too, huh?"
I blushed a little and nodded.
"Oh I know loads of girls like that!" He grinned, "From the completely convincing to girls who look like men in skirts!"
Although it was not obvious he was quickly building a picture of me, and when he eventually suggested we went to his place to watch a shemale porn movie I said yes.
Walking back to his off flat the fresh air mixed with the drink loosened my tongue and I was agreeing with him that it was amazing to think that such hot girls began life as someones son.
"Hell looking at some of them," I giggled "You'd never know what they are until you got inside their knickers!"
"Have you ever been with a t-girl?" Andy asked.
"Me, god no!"
Andy gave me a grin and added. "What about a bloke?"
I blushed and made an unintelligible sound that Andy correctly interpreted as a no, before saying. "That's a pity, because I think you're cute."
Have you ever actually felt the sensation of having the world freeze around you? Well that's how I felt when he said I was cute! I know a real para, active or retired would have decked him for such a comment, but it just gave me the collywobbels as I managed to stammer, "Thanks for the complement but that's not really my scene!"
It could have ended there but I foolishly looked at him, with a feminine prospective and realised that he was an inordinately attractive bloke. Six two, well built and very manly Andy had male model looks combined with impeccable manners and a razor sharp mind!
In the depths of my mind my conscience was telling me "Run this is wrong," but captivated by his animal magnetism there was an equally vocal part of my mind was telling me to go along with him.
He lived in a smart modern development down by the quayside and his home was very much a man's place. There was washing up in the sink, bits of a car engine on the table and a huge wide screen telly with all the toys!
"Um... Look Andy I've never done this before, or even told anyone that I like shemale porn until tonight?"
"Chill man!" Andy said, "I'm cool about it. Hell I like the same stuff because for me nothing beats a hot looking tart with big tits and a little cock, getting well fucked by a stud! Here, take a butchers at this?" Slipping a DVD in to the player Andy looked up at me sat uncomfortably on the sofa, asking. "Beer?"
"Yeah." I nodded, promising myself that I'd have the one beer, watch a little porn and then go home. As he stood up he brushed my arm as he pulled a couple of can from under the sofa, and the faint touch felt electric!
There was no messing about on the DVD, as it began with two girls making out on a bed, panning back the camera revealed that both girls had been boys, and as the scene built up I felt my cock getting hard in my pants.
"Gasping, "Fuck me?" I watched as both tranny's got spit roasted, by two hugely endowed 'performers'.
"Yeah!" Andy laughed, "Wouldn't you like to be in that guys boots?"
"Yeah, not much plot, but what the hell?" I giggled.
"Who cares about the plot, those two don't," Andy grinned, his hand accidental on purposely running over my thigh as he laughed, "Shit man, why can't I meet a bird like that?" He nodded to the telly were the blonde tranny was getting fucked doggy style.
I was an ex-Para with a bloke who fancied me watching a very hot transsexual porno! Obviously I knew the tranny's in the flick were, 'performers' who had likely made the money to alter themselves doing much worse than the hot and sticky sex scenes we were watching, but despite that I envied them... Jesus I would have given my right arm to have been like them. Sensitive to my mood, I heard him chuckle lightly and comment, noticing my bulging pants.
"I knew when I first saw you at the start of term that you'd really like this?"
My cock was like a ramrod in my pants, and I am sure I could hear the denim of my jeans straining to contain it. I felt myself going red as I gave Andy a surreptitious glance and saw him looking hungrily at the bulge in my pants. I felt scared, humiliated and yet oddly turned on as much by his attention as the movie.
"Good eh?" He grinned.
I nodded aware that his pants were as tight as mine, but I could not bring myself to really say anything more than, "yeah!" What else could I say? The film was a 'fuck and suck' fest so any attempt to discuss the plot or character development was a non starter as there wasn't any! Then I made my biggest mistake yet.
I looked into his hypnotic eyes, and saw that Andy really was a hot looking bloke who could have stepped from my dreams! Sensitive to my mood, he gave me a gentle grin and said, "Relax, and don't worry, I'll go slow, just trust me okay?"
I knew exactly what he was going to do, he was going to kiss me, I could see it in his eyes as he lent towards me... I did not want it, I was a Para for gods sake... but I did and I felt my head nodding as he kissed me lightly on the lips.
Oh god it felt nice, and Andy knew it, so he kissed me again and this time he did not mess about! It was a hard full on smacker right on my lips and this time I responded. It was like time stood still until he stopped and lifted his lips from mine asking with a smile. "Did you like that honey?"
Honey! I felt my guts twisting but his eyes held me like a rabbit it a gun sight, as I nodded unable to stop myself pulling him close for another kiss. When I had kissed women in the past it had never felt quite right to me, but with Andy... wow it was perfect!
His tongue was in my mouth, and I was like putty in his hands, and I could feel his hard cock pressing into me as we necked like teenagers on his sofa! With out breaking his kiss I felt his hand on my cock and oh my god did it feel good!
Sensing my positive reaction, Andy upped the stakes, and with his tongue still dominating my mouth I felt his hand flick the button of my jeans open, and then the zipper slid down! I felt like I was going to cum as his hand slipped inside my jeans!
I was wearing panties! I was so wrapped up with his kisses and presence that I had forgotten I was wearing a pair of silky satin French knickers...
"Sweet!" He grinned lifting his lips from my gazing at me with captivating look in his sex charged eyes! "I knew you'd like this!"
Jesus he had a million watt smile!
"God I must have seen you a dozens of times in the pub before I plucked up the courage to speak to you, and I knew there was something about you which turned me on?" He laughed, "And now I know what it was!"
I must have gone white or something, because Andy quickly added. "Don't worry, sweetie I won't hurt you but my those panties must be a little tight what with that sexy little hard-on of yours. How about I take them off and let your clitty lose?"
Andy must have seen my face because he whispered tenderly peppering my lips and neck with his lips and tongue, "Oh you sweetie, they are lovely and inside such loveliness can only lurk a sexy little t-girls clitty's, honey?"
He called me a t-girl for the first time and it made me feel wonderful... I must have sounded like I was strangling when I stuttered blushing brightly, "Oh my god, okay but please take it easy Andy, I.. I've never done anything like this, and I'm a little scared?"
"Shush babe, relax I'll go as easy as you want and it will be fine... just trust me okay?"
I nodded and said in a shaky tone, "Yeah okay but safe sex and all that?"
"Oh don't worry honey I've condoms, and will take care of you and see that its safe."
I realised what we had just said and I knew I had to go through with this now!
Andy gave me a grin and said, "Calm down honey, this will be fun, and you don't know how good it makes me feel to know that I will be your first!"
"Um... er?" I blushed and then admitted, "I've thought about a few times, well more than a few to be honest, but never taken things further even though I do so envy the t-girls?"
"Oh wow! You'd like to be like that?" He nodded to the telly, "A 'chick with a dick'?"
I nodded burning with shame. "Um, yeah... I like to dress as a girl, and have often dreamed of becoming a shemale, with blonde hair and big tits?"
"Well you've come to the right place then!" Andy grinned sliding my jeans down my legs... "And shaven legs?"
I blushed even more, as he added, "God you are so cute honey! Now sit back and let me make you feel really really good!"
Giving me one his captivating smiles, I sat back and the next thing I knew he was giving me a blow job! Hell did it feel good. It felt better than good, and as I floated in a world of sexual pleasure, I asked myself why anyone one would chose a woman, when blokes like Andy were as available! Obviously I had been with women in the past, mainly to show I had the 'right stuff' to my army mates, but those women paled in comparison to this... Andy's mouth was somehow so much better! After floating in bliss filled world for what felt like an aeon, I could feel the need to cum building as I gasped and moaned. "Oh my fucking god Andy... please for gods sake let me cum!"
If my old Para mates could see me now, begging the hunk of a man blowing my cock to make me cum I knew they would disown me, but fuck them! This was like the best sexual experience I had ever had and I was not going to let something like thinking of them bring it to an end as I begged Andy to bring me off!
Slipping my cock from his mouth Andy grinned up at me and said, "No honey, not yet... just trust me please sweetie."
His grin was like heroin, I would do anything to see that look on his face, hell I would even let him fuck me up the arse... Which was just what he had in mind! Giving my cock a last lingering lick, he slipped back on the sofa and said holding up a tube of 'silk' sexual lubricant. "I have this," adding with a very boyish lopsided smile. "Don't you think its high time I unburdened you of your virginity sweetheart?"
I felt my stomach sink like a stone as I said, "A.. Andy I'm not sure if I ready this?"
"Course you are babe." Andy grinned up at me with his eyes hitting me the full force of his 1000 watt charm as he pulled me on to the rug beside him, "And so am I, look see?" He jumped to his feet and shucked off his pants revealing his hard thick hairy cock as he rejoining me. Holding my eyes with his he took hold of my hand and placed it on his cock.
My eyes were like dinner plates at the sight of it, and I almost came as I felt it in my hand. Other than my own I had never handled another man's cock in my life, and I felt giddy with excitement at how sensual it felt! Hard, yet soft and warm against my palm I gently explored its shape and form hearing Andy chuckle, "Mm your hand feels so nice nice honey... Now are you going to give me your virginity?"
I could not stop myself nodding, "Yes."
"Mm, so you want to feel my cock?" Andy was grinning at me like the Cheshire cat
I could not speak more than the odd word, and gasped, "Yes!" His grin got all the wider, as I eventually managed to make myself say in a voice thick with desire, "Oh Jesus Andy, I cannot believe just how hot this is!"
"Sweetie, if you this this is hot and just wait until we get to the main event... Now why don't you give Master Andrew a kiss?"
"What?" I gasped, "Kiss you cock?"
"Yeah... I've given you one, now its time for my 'girl' to reciprocate!"
I felt like I was going to burn in hell when I heard myself saying. "Okay." My head felt like it was going to explode with pent up sexual frustration as I leaned over his lap and gently kissed his big purple cock head. Since I did not burst into flames, I tentatively moved my lips over the head flecking it with lots of tiny kisses, and feeling even bolder as Andy let out a low groan of pleasure I slipped it into my mouth.
His cock had a sexually exciting texture that combined with his musky manly scent that I found an intense turn on. Recalling what Andy had done to me, I hesitantly curled my tongue around his cock which made him sigh loudly with pleasure as he gasped, "Oh Jesus babes, you're wasted boy! You really are a natural cocksucker!"
Babe! Andy called me a babe and from that second any reluctance I might have felt evaporated, like the morning mist, as he said, "Lie back and lift your knees... Yeah that's my girl... Shit you look so fucking hot babes!"
I heard him squirt the lube on his hand and then he touched my butt! Whispering sweet nothings in my ears, Andy said, "Shush relax and enjoy, I'm not going to hurt you?" As I felt his large blunt fingers rubbing the lube round my arse, but when he tried to ease a finger inside me I almost leapt off the floor. Andy must have guessed that I was nervous and chuckled, "I said relax honey, we have all night?" Rolling round so he was laid down beside me Andy was well and truly in the driving seat, and he knew it as he again ravished my lips, as he continued to finger me.
After an indeterminate time, it could have been five minutes or five hours for all I knew, I felt a very strange sensation in my tail as he eased a finger into me. As we continued to kiss the finger he was fucking me with was joined by a second and then a third. God it felt good, to be touched and possessed in such an intimate way... and before long he had me panting, moaning and begging him for something more than his fingers!
He was not hung like the stud from the porno that was still playing on the telly, but to me as he rolled a condom over his cock, it looked huge and I moaned, "Andy please, be gentle... I fucking love this but please don't hurt me?"
"Shush honey, I'm going to take things slowly and make you cum like you have never cum before, now relax, lie back and spread your legs for me?" Andy chuckled between kisses as he lifted my legs and positioned his cock against my arse. With just the genteelest of pressure he began to push into me, and I felt myself gazing up at him as he eased even deeper inside me.
"Yeah," he encouraged, "That's a good girl... Once I get the head in the rest is easy... and then babes you'll really find out how good sex can be!
All the while he kept that same gentle pressure up and I felt his cock slipping into me millimetre by millimetre! Oh my god did it feel good... there was just enough pain to add spice to the moment, but not enough to cause any discomfort, and then as he sensed me slipping into bliss he thrust his cock deep inside me! For a moment I thought I was going to scream in pain, and then it felt amazing as his cock introduced me to a feeling that was mind bogglingly complex and seemingly directly wired to the part of mind that controls both pain and pleasure. It was like every pleasure receptor in my whole body had been turned on at once making me moan with unbridled lust!
All of a sudden I felt his pubic hair, tickling my cheeks as he embedded himself completely inside my body!
"There," Andy groaned, "I'm sunk to the nuts in side you," and then he pumped his hips, sending me into sexual orbit again!
"Fuck Andy, my god... I never knew it felt this good!" He pumped his hips again, making me babble, "Oh my god, oh my god... I never guessed it would feel this good."