Saturday, June 5, 2010

My First Boyfriend

I grew up knowing that I was different and early on I always tended to be a bit more domestic. I wasn't necessarily effeminate, but I did dress in my mother and sisters clothes from an early age.
The Summer I was getting ready to enter high school a family moved next door. They had a son who was going to be a junior and by all accounts he was an absolute football stud. "Jack" was 6'-3", 195 and was a Division I prospect. He was a nice guy too and attracted alot of female attention too.
Being neighbors I saw him alot and he was generally pretty friendly towards me (especially since I was't athletic). One day we we at his house hanging out and he brought out some of his Dad's Playboy and Penthouse magazines. Naturally the talk turned to sex and as that stage I was a virgin and had only begun to think about having sex. Somehow in our discussion I mentioned that I had dressed as a cheerleader for Halloween the previous year.

Jack looked at me curiously and said he would love to see me dressed as a cheerleader for him. Since we both were home alone during the days I didn't see any harm in indulging him.
My older sister had been a cheerleader and since I was pretty small (5'-6, 145) I could wear all of her clothes.
To my surprise Jack was very impressed by how I looked dressed and instead of making fun of me he actually encouraged me to put on some of his mothers lingere for him.
I felt so naughty and sexy getting dressed and I can still remember the charge of putting on his mothers eyeliner and mascara at her makeup table. When I was all dressed Jack came over and sat on the bed at told me how pretty he thought I was.
He leaned over and kissed me and I thought I was going to ejaculate from the excitement. We kissed for a good solid hour and then he pulled his cock out of his pants and asked me to give him a hand job.
I was only too willing to do what he said.I was so aroused seeing his hard cock that I did as he instructed and stroked him to a very hot orgasm. His cock shot a big hot load of semen all over my hands and he told me to be a "good girl" and lick his cum off my hands...........I did with lust. He kissed me and said he wanted me to be his "special girlfriend"
I was so aroused by the thought of any kind of relationship with this stud of a guy I knew I was going to be his "girlfriend" for the immediate future.
The next day I went to his house at 9:00am and then and there I gave the first blowjob of my young life.

The rest of the Summer any time that he wasn't practicing football I was at his house getting all dressed up for him and on my knees sucking his cock.

I began to become a very accomplished little cocksucker and Jack was as sweet a boyfriend as a girl like me could have ever asked for. I loved to please him and I would suck him for hours on end.

Jack and I fucked bareback from the start and I had my first anal orgasm with him.
He could be gentle and until I asked him to be rougher with me he was the perfect gentleman. He was also just as horny as you would expect a 17 year old guy to be and he could blast 5-6 loads of cum a day into my waiting mouth or ass.
We saw each other for the remaining two years he lived in town and we stayed in touch for a while even after he left to a major university to play quarterback.
Jack was the first love of my life and I still think of him very fondly.


Andrea Kitten said...

How sweet! the first ones always special!!

Anonymous said...

That sounds very nice. Recently I have been thinking about getting a boyfriend, one who encourages me to be more feminine and we can have fun together. This story makes me a little envious, hehe.

greenhawk46 said...

I'll bet you were a real turn-on for him too-that always helps-nice memories xxx Jim

Karen said...

My first boyfriend story starts from a pretty young age, I guess I must have been in the last year at high school. Years before I met John I was experimenting with my mothers clothes and make-up and had begun to have my own collection of stolen clothes and make-up.

John was a friend of my older brother, some three years older to be exact. Over the summer months John would often sleep over at our house were in all cases he would have to share my bed as I was a lot smaller than my brother.

What started out as a normal situation soon turn out quiet different.

It was a Sunday morning after carnival day. For the carnival my mother insisted that I go as a glam rock star. This meant me wearing a red silk blouse, a pair of silver shorts loaned by a neighbours daughter, pair of silver tights, my mothers friends silver knee high block heeled boots. My mother and her friend made my face up with foundation, rish red blusher, the deepest blue eyeshadow and loads of eyeliner and mascara.

The day went well, and the festivities of the night turnm out late which resulted me in going to bed with my make-up only partially washed off, wearing the silk blouse and tights (I had no knicker son that day as Mum wasn't that good).

Waking up in the early hours of that morning next morning with John lying behind me I was aware that his hand was on my hip and there was something hard pressing against my bum through my tights ,he was kissing my neck and trying to get closer to me. I moved away and JOhn woke up. He was full of apologies and said that he must have been dreaming.

I feel of a mans power over me, and his wanting to take me with his manhood, wanting me to be the object of his desire and satisafaction whilst in those feminine clothes changed my life forever.

Two weeks later I gave John my first ever hand job, I remember being shocked at the sheer size of his cock, and more so realising that I was not really a man for my cock was tiny.

A month later it was my first ever attempt at giving a man a blow job and feel in love with the feel of a mans girth press against my lips and hear him moan at my efforts to satisfy him. Six weeks later I swollowed cum for the first time (and have been addicted since)

I wore my black skirt, white blouse and six inch heels for my fist cock in my hole. John was nice and kissed me before pulling my skirt up, my tights and knickers down and then filling with his gorgeous cock. I was taken that day for the first of hundreds of times. Being my first boyfriend he was honoured each time with delivering me a cream pie.

I would wonder for hours after with the warm glow of his passion, his cum seeping out of me , damping my knickers beneath my jeans

There should now be a whole load of men hankful to JOhn for making my life so complete, so gurly, so sassy sissy

(Please use this story for your site if you wish)


Talvenada said...


Loved your story. How soon did John make his first sleepy oh-my move? What and when was his 2nd move? It's a hot story. Please share.



samislut said...

the first time we realize how much we love our friends' cocks and get the nerve to touch one and then lick it and suck it and become a girly-boy sissy faggot forever is the best memory of our lives-- at least is of mine.

Karen said...

It was a couple of weeks later that John stayed over again. Sunday morning he was again lying next to me in my bed. We had agreed that he would sleep top to toe because of the problems last time. This time of course I was only wearing my grey night shirt as I really have always felt uncomfortable wearing PJ bottoms as they tend to wrap around you during the night.

So Sunday morning my brother had again gone to work, I woke up and lay in bed dozing in and out of sleep.

I thought John was aslepp when I realzed that he was staring at me. I looked over and he was giving me this really strange smile. I could see that he was masturbating under the quilt cover. I got up from bed and sat on the edge of the bed in shock.

John motioned for me to come over , I of course said no. He pulled the quilt cover back and revealed his huge cock and his hand warped arond it playing with himself. He asked if I would wank him off. I of course said no

For the first few months I couldn't work out why I couldn't get off the bed that morning and go out of the room to avoid this situation, now of course I know that it was becase that I was a budding sissy.

I at first refused to play with his cock , but sat there staring at him amazed at the size of his big cock. I thought how tiny and pathetic mine was in comparison. John continued to play with him self stretching his body fully as he slowly move his foreskin up and down his shaft.

He kept asking please wank me. I must have looked so undecided. I reached over slowly at first just resting my hand on the bedsheets beside of him. Then I placed my hand on his hand a let him wank himself with my hand held over his. I remember both the warmth of his hand and how natural it felt, to be holding the hand of a man. More so I remember the smell of cock, it was the most amazing smell, manly, sexy and powerful.

John took his hand off his cock and let it stand rigidly to attenton. My hand rested on his thigh. I ask me again to play with him. I lifted my hand and took his cock,grasping the girth of which my fingers barely met.

I could feel the strength, the heat, the power of his cock pulsing through my hand, it was hard and oh so big. He held my wrist and began to move my wrist up, simulating me actually wanking his cock. After a few moments John let go of my hand without hesitation and I wanked him freely.

It was so amazing that I was able to bring this much pleasure to somebody else, that somebody else being a man. Pulling at his cock wanking him faster, then slower try different ways to see his reaction. I realised that my life had in some way joined up. The flurting with my mothers clothes and make-up, the sissy taunts that I had suffered life long all came together as I held and wank my first ever cock, my first man.

Needless to say John came strongly and spurted cum into the air both over his stomach, his chest, my arm and all over my hand. I moaned as he came, he carressed my thigh as he came letting his hand rest on my thigh

I think he was a little embaressed after the released as he rushed off to the bathroom. I sat there on the edge of the bed, legs crossed smoothing the load of cum across my hand, smelling it and savoiring it.