My Wonderful Secret Ch. 03

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Andrea continues her struggles as a t-girl.
4k words
4.52
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Part 3 of the 4 part series

Updated 10/24/2022
Created 02/02/2006
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Ilbfita
Ilbfita
103 Followers

Things were going pretty well with Mark and I, and with my life in general. I loved the freedom of university. I had a boyfriend whom I loved and who loved me, and he was also my best friend. We got on really well and shared so many interests. If we weren't 'together' we might still have been good friends. I was growing in confidence every day and was finally learning to accept who I was and to even like myself.

My older siblings had gotten jobs and moved out of home. My younger siblings took advantage of the newly available bedrooms in our house, and got on with their own lives and senior school. Home life was calm and happy, and I was pretty much left to my own devices. My mother had taken a sudden interest in my diet and I was awoken to orange juice and fresh fruit every morning, but that was just normal craziness for my mother. She still cared for me. I couldn't remember a time when I had been as happy. These may have been the happiest days of my life.

Each Friday afternoon when I finished uni at about 2pm, I would head to Mark's and change into Andrea. He would get home about 5pm and our weekend would begin. We would immediately start to cuddle and kiss, share a bottle of wine, and just unwind. Slowly he would start to run his hands all over me and stroke me through my panties; the sexual tension between us would build to a point where we were both breathing heavily and his hard cock would press against my body.

Without words we knew what to do next and that normally meant Mark sitting back on the lounge and me kneeling between his legs and releasing his cock from his trousers. I would stroke it and lick it and tease and taunt him, before eventually allowing it to slide into my mouth. In the early days I was clumsy and nervous and embarrassed, but now I loved sucking him and loved taking my time with him. I would stop and talk to him, make him laugh, suck his balls, kiss his inner thighs. I had learned to talk dirty to him and him to me. I could make sucking him last up to half an hour and by the time I let him cum he exploded and screamed like a man possessed. This is what we called love making.

I liked it when Mark stroked me through my panties, but I didn't want him touching inside my panties or even removing them. I was ashamed of my penis and preferred not to see it, especially when we were together. My penis was very small and my balls seemed to be getting smaller, and that suited me fine. I had no desire to be a man like him, and although I envied the simplicity of his life in comparison to mine, I knew I wasn't a normal boy and that I never would be.

He told me I rocked his world and that he couldn't wait for Friday to come around. I told him that it was my love for him that made me learn to suck him so well. My love would make sure that each time I sucked him it would get better. He would kiss me deeply and wrap his big arms around me and hold me tight. I felt so loved.

When he had composed himself we would normally order in and start playing on our computers. We would battle other geeks in a MUD from the university, stopping occasionally to kiss and cuddle and maybe for me to suck him again, before packing it in at about 2am, and falling to sleep in each other's arms. Saturday was sleep in morning, interrupted by love making. Saturday afternoon was study time at the uni. We normally studied separately so that we weren't distracted. Saturday night we went out somewhere to eat and have a few drinks, before back to his for more computer games and love making.

Sunday was another sleep in, followed by the cross town markets, where we would eat Asian food and watch the street performers do their stuff, then back to his place again for more kissing and fun. By 9pm I was all dressed up as a boy and Mark, would run me home in his car under the cover of darkness. Sometimes we kissed good bye but I was still so frightened of my mother that I usually opted to just squeeze his hand and say my goodbyes. Usually I could sneak into my flat without any attention from my mother.

As I pulled the sheets over me I would breathe a deep sigh of relief. My life was great, but it was still a long way from being perfect. I was still pretending to be a boy to the world, when I knew I was really a girl and that I needed to live my life as one.

Another small issue I faced was that Mark desperately wanted to have intercourse with me. I had asked him about it after we went to a party where couples were screwing each other all over the place. He told me that he desperately wanted to do it with me. I didn't really need to ask him, as I could feel his body twitch and his hips subtlety thrust against me, every time we were entwined, and I observed how awkward he became whenever we saw a sex scene in a movie.

Mark wanted it bad, but he was a gentleman and said he would never ask me or pressure me. If we were going to do it, I would have to ask him. When the time was right, I would know and I would ask him and that would be that. And there was the problem! I didn't really want to do it. I had tried shoving various things up my ass but just found it a lot of work for very little reward. In short it was boring and it did nothing for me. Of course I wanted to do it with Mark and I wanted to do it for him. I wanted him to be able to fuck his girlfriend like a normal guy would. I wanted to make him happy and to that end I persevered.

Trouble was, I didn't know where to start. I am a small person and my ass is very small and tight. There was no internet to download from; there was no friendly neighbourhood doctor I could talk to. I experimented with knives and forks (the handles of course!), candles, torches, anything that was roughly the right size and shape. None of them did it for me.

Eventually I resorted to trawling through the library in particular the sociology section which had a lot of books on human sexuality, but there was very little useful information for me in there. Physiology promised a lot but delivered very little, other than fascinating diagrams of men's and women's genitals.

Finally I stumbled upon a book called "Variations in Human Sexuality" which as the name suggests, was quite an old book but it did offer this advice to what it termed "the receiver" in "male-male intercourse."

"Anal intercourse is an unnatural act but if the receiver is determined to defile himself then he must train his anal muscles through a gradual stretching process. This should commence with lots of water based lubricant as oil based lubricants may cause irritation in the lower bowel. Starting with small, smooth, unbreakable cylindrical objects, the receiver needs to gradually increase the size of the object until he can accommodate the approximate size of the erect penis of the inserter."

I was grateful for the small snippet of ultimately very logical information, and ignoring the author's prejudice, I set about finding an appropriate source of small, smooth, unbreakable cylindrical objects. This was not as easy as it seems. Then I discovered carrots! Carrots were 25 cents a bag and came in a variety of sizes. They were healthy and mother had no problem buying them for me. After trying them 'au natural', I learnt that they were easy to cut and shape with a small paring knife. I actually became very skilled in turning the common carrot into a beautiful miniature penis. A quick rub with an abrasive kitchen cloth would render them smooth, and after soaking them in warm water until they reached 'cock temperature', they were the perfect DIY training cock.

I didn't enjoy pushing them inside me, but I did gain a certain amount of pride and confidence as I became able to accept bigger and bigger carrot cocks. Eventually I worked my way up to Marks cock size. The carrot took a good hour to craft into Mark's shape and size, but when I finished shaving and scraping and gave it a good smoothing then a dunk in the hot water, I was as horny as I'd ever been, and eagerly engulfed the carrot, wishing that Mark was with me and that I had his cock in my mouth.

The Mark replica carrot cock took some working into me, but I got there. It did not feel great, but it did not feel bad either. Regardless, this was all about giving Mark what he wanted, not about my pleasure and if I could take the replica carrot, I could let Mark enter me and make him happy. I hoped that in time I would learn to enjoy intercourse, but to begin with, I just wanted to look after my man. Who can blame a girl for that? Besides, Mark's birthday was coming up and I had a plan to make it one he would never forget.

We met as usual on the Friday afternoon. I had gone to a lot of effort to squeeze into my latest LBD. Beneath it I wore a tiny black g-string and black thigh high stockings and I had put out all stops with my makeup. My long girly eye lashes were darkened and thickened, lots of foundation and subtle blush to highlight my high cheek bones, and for the first time ever, cherry red lipstick. I'd been practising almost daily with my makeup, and I now felt very confident with it.

Mark's jaw dropped to the ground when he first came home and saw me standing in the door way to his bedroom. He jumped me, picking me up like a rag doll and engulfing my lips, invading my mouth with his tongue, whilst his hands squeezed and clawed at my thighs and ass.

"You look so fucking hot!" he hissed as he came up for air, before resuming his passionate assault on my lips.

"Sit down, honey, I have a present for you." I said in my softest, sexiest voice when I managed to break his hold. I directed him to the lounge. Instantly he dropped his trousers and revealed his massive erection and sat on the lounge with a crazed, horny twinkle in his eyes.

I went and got the carefully wrapped gift, then knelt between his legs.

"Oh honey, look how big and hard you are! I think that cock is much too big to go in my mouth, don't you?"

"You know it isn't! Come on baby, give me my birthday treat. Don't tease me."

There was a hint of desperation in his voice, but I was enjoying teasing him.

"Oh my! If sucking your big cock is a birthday treat, then you only get to cum once a year. Is that what you want, honey?"

"Please baby, please suck my cock, don't tease me anymore, I'm so hard I feel like it might burst."

"Mmmmm. Well I wouldn't want that. Maybe I could give it a little lick, just to test how much pressure has built up?"

I ran the very tip of my tongue up his shaft and then slowly back down. I stopped, licked my lips as if I was tasting them.

"Oh honey, it is very tight. You might be right. What should I do to stop it from bursting?"

I was looking up at him, with my finger in my mouth, doing my best bimbo impression. He was squirming with desire and pent up sexual energy. I had never teased him like this, but I had to admit, I was enjoying myself.

"Please baby, suck on my cock like a good girl. You know you like it. And it will make me so happy. Please?"

"I tell you what, you open your present and then I will do whatever you want. Is that a good deal, honey?"

He couldn't make words so he nodded frantically and sat forward to receive his gift. With trembling hands he tore of the wrapping paper to reveal the beautiful wooden box. Inside it was an authentic, early wooden, handmade slide rule. Mark like me was a geek, and he loved anything mathematical.

I saw a tear well up in his eye, as he just stared at the exquisite detail and craftsmanship of both the slide rule and the box.

"It's awesome" he said in a soft voice. His erection had completely subsided, which disturbed me somewhat, given what I had planned for him, but I was moved by his obvious appreciation of my gift. He continued to stare at it.

"Why don't you take it out and look at it?" I suggested.

He tilted the box slightly and gently lifted the ancient device out from the box. That was when the condoms I had placed underneath the rule fell out landed with a crinkly splat on the floor.

He looked at the condoms and then looked up at me. Our eyes met and locked onto each other's.

"Mark, I want you inside me. Right here, right now."

I stood up, took his hand and led him to the bedroom. I tore off my dress and lay on the bed, naked but for my g-string and thigh highs. Nervously he removed his clothes and lay on top of me. He kissed my eyes and nose and lips and worked his way over my neck down to my nipples.

"I can't believe how red and plump your nipples are!"

He said between licks and sucks of my tender protrusions. His sucking only served to make them redder and puffier and so sensitive that I had to ask him to stop.

"It must be that new dress," I offered as an explanation, as I guided his face up back up to mine and our lips locked together, allowing me to slide out from under him.

I turned so that my naked ass was pressing against his slowly stiffening cock. It turned me on to feel the heat and rigidity of his member grow against me.

Slowly he began to kiss the back of my neck and I moaned a soft moan of deep relaxation and contentment. Gently together we were starting the next great adventure of our relationship, and only our love for each other prevented us from exploding with nervous tension. When I felt he was really hard I rolled onto my back, and, passing him a tube of lubricant, I whispered

"Get me ready."

I slipped off my g-string and guided his nervous hand between my legs, lightly brushing my stiff little clitty (as I preferred to think of it), and gently pressed one of his slippery fingers against my virgin hole.

"Make little circles, honey, get my pussy nice and wet and ready for your cock."

I couldn't believe what a slut I sounded like, but I knew I needed to teach Mark how to get me ready. He pushed in, too hard, too quick.

"Gently honey, gently!" I cried out softly. I realised that I needed to let him know what felt good for me, and that I needed to encourage him when he got it right, rather than tell him off when he got it wrong. I used my sexiest, sluttiest voice.

"Get me ready nice and gentle, you've got all night to fuck me, so just take it easy. That's it, oh yeah! That's how I like it, oh yeah, you're fingering my pussy so nicely now."

He resumed his deep tongue kissing and I kissed him passionately in return. Slowly my hips started to grind against him, pushing more of his finger inside me, and turning me on more and more.

I can't explain the feeling of his long finger pushing inside me. It was horrible and yet wonderful, exciting yet frightening, and sickening yet delightful all at the same time. This insane conflict between mind, body and instinct made me feel more alive and aware of my body than ever before.

"Put more lube on your finger baby, I want you deeper inside me."

I didn't have to spell it out to him. After fumbling with the now slippery tube I felt his finger slowly work its way deeper inside me.

"Oh yeah, honey, that feels so good having you deep inside me like that. Keep moving it in and out, get me nice and stretched for your cock. Oh yeah that feels so good."

He resumed kissing my lips then moved to my ears, eyelids, neck, nose, eyebrows.

"Oh yes, oh yes! Use two fingers! Get me ready for your big cock." I urged as his finger now moved inside me so easily and his tongue and lips worshipped every inch of my face.

I went insane when I felt a second finger invade me. I was so into this weird feeling of losing control of myself. It was un-natural but I liked it.

"I need you inside me now" I whispered.

He broke his kiss and slid out of bed. Recovering one of the condoms and desperately trying to open the wrapper. Finally he got it open and I felt a spasm of anticipation as he rolled it down his shaft. I passed him the lube.

"Get that cock nice and slippery honey, I want you to slide inside me."

I wasn't taking any chances, I really wanted that cock well lubed up. Meanwhile I moved my ass to the edge of the bed, placed a pillow under my lower back, and spread my legs so that I could watch my man approach and mount me.

"Come on baby, nice and slow to start with, push inside me now please."

I felt the slippery head of his cock press against my tiny opening. It was like the world stopped spinning and time was fixed in slow motion, except for our heartbeats which were pounding like jungle drums.

He gently pushed forward and the head slipped in so easily, but then I felt an involuntarily clench which really hurt and I yelped in pain. He quickly pulled out and stepped back.

"I'm so sorry, baby, come on, let's stop this now."

"No no no, Mark, it's ok. I need you to be a man for me and push inside me. It will hurt me a little bit but that is normal. I need you to hurt me, I want you to take me, and I want you to watch my face as you take my virginity."

I could hardly believe I just said that but it came out. It was the truth. I wanted this so much I was prepared for some pain. I needed Mark to man up and fuck me and get it over with.

He moved between my legs and leant down and kissed my lips.

"If you are sure, baby?" he whispered.

"I've never been so sure about anything!" I whispered back.

He stood up and put his cock against my hole and pressed forward. It slid in, slowly but easily, I could feel my body stretching around him as each millimetre advanced. Again there was an involuntary clenching muscle spasm and the pain was over-whelming. I couldn't help but let a painful moan escape my parched lips.

"I'm sorry, baby. Let's face it, it's not going to work." Mark muttered frustratedly, roughly pulling out of me and stepping back. His face was red and tears were in his eyes. This was not how it was meant to be and I knew he was not enjoying it as he was meant to. But I was not going to be defeated.

"Dammit Mark! I want this this! We were nearly there! I want you deep inside me. I want you to fuck me hard and fuck me deep. I want you to take my virginity. I want you to accept my gift to you. I want this and I need this. I need you to grow some balls, man the fuck up, and hurt me. And if you're not up to the job, I'll put my little black dress back on, and go down on the highway and pick myself up a real man and let him take me."

I had barely got those words out when Mark marched up to me, spread my legs wide, positioned his cock at my opening, and slid himself inside me. He was gentle and slow yet forceful and determined. I screamed in pain and shook my head violently in protest as another muscle spasm clamped down upon his cock and tried to repel the stiff invader. But this time it was too late. He was buried to the absolute hilt inside me.

My virginity was gone along with my innocence and any remnant of masculinity. A tear of pain, sadness, joy, shame, fear, horror and elation all rolled into one formed in my eye. I had surrendered to my failings as a male and my love for him. The pain was intense but I knew deep down that I had no one to blame but myself. This is what I wanted.

I looked up at him. His eyes were burning into mine, his expression a combination of anger, fear, aggression and triumph.

"This is what you wanted? Well now you've got it," he hissed, "and now I'm going to fuck you!"

The pain did eventually go away, but it was not replaced by sexual pleasure as I had hoped but I wasn't disappointed. I found myself enjoying feeling my man slide his cock in and out of me, and I enjoyed watching him fuck me. It was at best, physical pleasure much like a good hard massage, not sexual pleasure. I was just happy that I could give this gift to my man. I reached up and wrapped my arms around his chest, pulling him on top of me. He smothered me with kisses while maintaining a steady rhythm.

"Does that feel good, honey?" I asked breathlessly.

"Oh yeah, it's amazing" he grunted, his aggression easily checked by the pleasure he was receiving, "Is it good for you too?"

Ilbfita
Ilbfita
103 Followers
12