First Time With A Guy

One Saturday morning I awake to find the sun shining through my bedroom window. It looks as if it will be a beautiful day and I feel wonderful as I remember the dream I was having just before I woke up. In it, I was being fucked deeply up my ass on all fours by a beautiful blond hunk with a lovely long and hard cock while sucking on the cock of his twin! I was dressed in an ultra sexy hot red latex corset with garters and stockings and matching thigh high boots. Of course, as is usually the case, I woke up just as my dream hunks started to cum…

My cock is throbbing within my tight pink silk bikini panties under my sexy pink silk nightgown and I feel so sexy and feminine as I stretch my long hard body against my satin sheets. I fondle my throbbing cock and squirm in bed as I fantasize the ending of my dream when suddenly the phone startles me. It is Tom, the painter I have scheduled to come by to paint my kitchen. I have never met him, but he sounds very nice and was recommended by a friend. He tells me that he will be arriving within 30 minutes and as I hang up I am disappointed that I was again interrupted before climax.

Getting out of bed, I head for the shower where I slip out of my nightgown and my panties. After a quick shower, I choose my outfit for the day. Normally on the weekend, I would dress up in a sexy girl's outfit and wear makeup, but today since the painter is coming, I can't fully indulge my feminine side. Nevertheless, I decide to wear some sexy lingerie under my male clothes. I choose a pink satin garter belt with lace trim and matching bra and panties. I attach the garters to sheer white back seamed stockings with lovely lace trim. Over this I put on a pair of tight black leather pants (which always feel very sexy as my stocking clad legs and silk covered buns rub against the smooth leather) and a t-shirt and slip on my moccasins. Just as I am finished dressing, the doorbell rings and as I open it I feel momentarily breathless as I gaze into the eyes of a gorgeous blond hunk that could have come straight from my dream of the night before! I wonder if he notices how flustered I am as I stammer a greeting and shake his hand. He is so beautiful! He is about my height and startling blue eyes dominate his handsome tanned face. A tight t-shirt is stretched across a sculpted broad chest, which tapers to a narrow waist. He is wearing very short and tight blue jean shorts, which reveal his muscular and tanned legs and thighs and good size bulge where his cock and balls are hidden.

As I lead him to the kitchen, I feel all of a sudden very shy and a little self conscious as I imagine his eyes on my tight leather clad buns. To give you a little background on me, you might imagine, based upon what I have told you thus far, that I am gay and long out of the closet. Actually I have never really been with a man before as an adult (as a teenager, I was seduced by older men twice and both times only let them suck my cock). I am 32 years old and have been dressing up in secret as a girl since the age of 14. I live alone and am currently single, although I have had several long term relationships with women. I'm 6' 1", 180lbs., 7", blond, blue eyed, and I have an athletic swimmers body. I am considered to be very good looking and masculine and no one (other than one past girlfriend) has ever learned of my secret feminine side, or my fantasies of being with a man.

Anyway, as I mentioned, as I am leading Tom to the kitchen, I feel like he is probably looking at me and thinking that I am " a flaming fag" dressed as I am in tight leather pants at 9:00 in the morning! Suddenly in the silence, I become conscious of the fact that you can hear the leather of my pants sliding against my stocking clad legs! Noticing this causes me to try to walk without so much movement and almost at the same time, it occurs to me that he may be able to see the straps of my bra against my shirt! By the time we cover the short distance to the kitchen, I am blushing as I imagine what he must be thinking.

Tom gives no sign that he has noticed anything, although, and it may just be my imagination as he begins to set up, that I catch him glancing covertly back with a slight smile at the growing bulge in the crotch of my leather pants. This just makes my cock throb all the more and my tight ass to squirm within the tight confines of my panties and leather pants.

I haven't yet had anything to eat, so as Tom goes about preparing the kitchen for painting, I sit down at the table with a bowl of cereal and watch him work. What a dreamhunk he is! I can clearly see his sculpted muscles beneath his tight shirt and I long to strip those tight shorts off to reveal his tight buns! Suddenly, he stops what he is doing and while facing away from me, he strips his shirt off to reveal a tanned and muscular broad back. I am so mesmerized by the sight, that when he turns suddenly he catches me looking lustfully at him and I glimpse a little smile as I turn back to the magazine I'm reading.

From then on, I try to be more careful, but I simply can't stop myself from looking at him. I am squirming on my seat and my cock is throbbing hard within my panties and tight leather pants. His chest is bare and beautiful with hard pointed nipples. He has a washboard rippled stomach. From the bulge in the front of his shorts, I guess that he must have a big cock, I can only imagine how big it must be when it's erect!

The coffee machine finishes brewing. I have purposely made extra, just in case Tom would like some. I offer it to him, and he joins me at the table. We talk about various things and at one point he asks me if I live alone, I reply that I do and then, blushing, I ask if he does too. He replies with a smile that he does. I don't know if he realizes what an effect he is having on me, sitting so close that I can smell the sexy scent of his body. Without realizing what I am doing, I raise and cross my leg and removing my slipper, I nervously fondle my stocking clad foot, right in front of Tom! We continue talking about the work he is doing for me, when suddenly I notice that he is looking right at my foot and the raised cuff of my pants which has revealed several inches of my stocking clad leg! Flustered with my face turning red, I immediately lower my leg and slip my foot into the slipper. I stammer on about some aspect of the work and Tom just looks at me with a beautiful smile, and a knowing look on his face. I hurriedly finish my coffee and leaving him to his work, I retreat to the bedroom.

Laying down on my bed, My mind swirls with confusion and excitement as I think about Tom. What did that smile of his mean? And why did he ask me whether I lived alone? Is it possible that he is gay or bisexual and is attracted to me? The thought is almost too wonderful to imagine!

Setting aside all thoughts beside the overwhelming fantasy image of being with Tom, I slip out of my tight leather pants and standing in front of the mirror, I caress my hard and throbbing cock through the sexy silk of my panties. As Tom will be occupied for some time, I decide to dress up here, in the privacy of my bedroom and indulge myself in fantasies. Going to my dresser drawer, I remove my silicone "boobs" and slip them into my bra. I then take an ultra sexy pink leather minidress from the closet and slip it on. Oooh, I feel so sexy and feminine running my hands along the sides of my dress, which is tightly molded to my body and just barely accommodates my jutting boobs and is so short, it just covers my panty clad buns. I put a couple of berets in my long blond hair to make me look feminine and apply shiny lipgloss and makeup. Then, I take my thigh high pink leather boots that match my dress and slip my long stocking clad legs into them.

Laying back on the satin sheets of my bed, I gaze up at my reflection in my overhead mirror. I must say, I look very hot and sexy. With my athletic body and masculine features, I don't think I could pass as a girl. What I see when I look at my reflection is a good looking man, with an athletic and tanned body clad in ultra sexy and feminine clothes and a handsome face softened with light makeup and framed by lovely long blond hair.

I begin to fondle my achingly hard cock, which is clearly outlined against the tight confines of my leather minidress and run my other hand over my leather encased jutting boobs. I imagine myself caressing Tom's gorgeous hard chest and slipping my hands around to fondle his tight ass as I mold my body against his and feel his hard cock pressing against my own… Sliding to my knees, I face the outline of an enormous cock pressing the front of his tight denim shorts. My hands tremble with anticipation as I unzip his shorts and what must be a 10", hard and beautiful circumcised cock pushes itself out (no underwear!) until the pre-cum covered head is pressing itself against my glossy lips… At this point I am so turned on that I feel I could cum at any moment, so I get up to retrieve my dildo (a molded replica of Jeff Stryker's), so that I can have it between my lips, or my buns when I cum.

I decide that I want to fantasize that Tom is fucking me, so I cover my dildo with lube and attach the suction cup base to a low stool I have for this purpose. I then raise the hem of my leather minidress and lower my panties and lower myself until the tip of the "cock" is pressing against my tight virgin asshole. I am imagining Tom's strong hands gripping the my leather clad hips as he lifts the hem of my dress and lowering my panties, presses his throbbing cock between my virgin buns when suddenly, I hear Tom's voice calling me and his steps approaching along the hallway. In panic, I pull up my panties and grab my "cock" from the stool and run to the closet. I have just slipped inside and partially slid the door closed, when simultaneously the door to my room opens and my dildo slips from my hands and lands between the crack of the closet door.

I dare not move as I see Tom enter the room and look around for me. Seeing no one, he walks over to the bed and I am astonished to see him pick up my leather pants and hold them to his face and inhale the smell of the leather. He then sits down and begins to take off his shoes and socks. I am captivated by the sight of this beautiful man getting undressed in my room. My cock is pressing hard against the constraints of my panties and leather dress as Tom slips off his shorts to reveal a bright red bikini thong that is practically bursting at the seams. Then he slips off the thong to reveal the biggest and most beautiful cock I have ever seen! It must be at least 10" long!

The mystery of why he is undressing in my room is resolved when he picks up my leather pants and begins to slip them on. I guess he has a leather fetish, like me! It seems to be a slightly tight fit, especially when he tucks his giant cock in and zips them up, but oooh, does he look sexy as stands facing me (and the mirror) and caresses his cock through the tight leather of my pants. I can barely stand it, I'm so hot for him! My cock is straining against the front of my panties and tight leather dress and I slowly reach down and begin to fondle it, taking care to restrain the moans of excitement that I long to make!

Suddenly, his eyes shift to the floor near my feet and I notice to my dismay that the cock head of my dildo is protruding from the closet door! I hold my breath as Tom approaches, and kneeling reaches out to pick up my dildo. At that moment I'm trying to lean back further into the closet and I bump into some hangars, drawing Tom's attention to me. He stands immediately and as I open the door and step forth, he looks a little frightened, but his eyes widen as he sees how I'm dressed and he says, "Oh god, I am so embarrassed! You've caught me dressing in your clothes!"

Of course, my own cheeks are flaming red in embarrassment, as I respond, "oh, don't worry about it, I don't mind. They seem to fit you very well. I didn't mean for you to see me dressed like this, I hope I haven't embarrassed you Tom! I guess you already had an idea that I like to dress up like a girl".

"Oh, don't worry about me. I did happen to notice earlier that you were wearing stockings under your pants and I could see the outline of your bra under you t-shirt. You look really gorgeous dressed up like a girl. You look sexier than any real girl I know", he replies.

His words excite me and against my will, my cock springs to life and despite my will, in front of his eyes my cock presses forward against the tight leather of my dress until it is clearly outlined. I smooth the sides of my dress and squirm a little with lust for him as I purposely stare at the answering throbbing bulge in the front of my own tight leather pants he is wearing. "Oh, you look very sexy yourself Tom. It looks to me though, as if there is one area where those pants don't fit so well".

Tom looks a little unsure of himself as he replies, "oh really, where?"

Stepping forward I lay my hand against the throbbing outline of his cock, "right here they seem a little tight", I breathe into his ear. I can feel the pulsing of his cock through the tight leather and I grip it tightly as he moans in pleasure. With my other hand I reach behind and fondle his tight leather clad buns. Suddenly Tom places his strong hands around me and gripping my hard buns, pulls me to him, pressing his sexy full lips against my glossy ones and slipping his hot tongue into my eager mouth.

Can this really be happening I ask myself as I mold my body against his and let my own tongue swirl within his sweet mouth. Soon we are both moaning in lust for one another as our throbbing cocks rub against each other through the tight leather. Tom has now slipped a hand beneath the hem of my dress and is caressing my buns through the tight soft silk of my panties.

Breaking free for a moment from his kiss, I let my tongue swirl over the delicious salty skin of his neck. "Oh Tom lover, it feels so good to be in your strong arms. Your body feels so good. I want you so badly lover." As I am saying this I am gripping and squeezing his sexy buns through the skin tight leather.

Having already seen his lovely cock, I know what I want, so I begin moving my lips and trailing tongue in that direction, pausing to lick and suck his strong shoulders and then down further to nibble and suck his hard sweet nipples. As I am doing this, Tom is moaning with lust and excitement and begins fondling my boobs through the tight leather of my dress. "Does it turn you on to imagine me as a girl Tom? I want you to treat me like a girl and dominate me lover. I want to please you and will do whatever you want. Call me Bootsie."

"Bootsie, you are so sexy. Don't worry, you are a girl in my mind and I'm going to complete your transformation by fucking you as only a man can. Oh yes girl, suck my nipples!"

Tom's words are so incredibly exciting! I begin stroking and fondling his hard leather covered cock with one hand as I suck and nibble on one nipple, while fondling and squeezing the other. I am squirming and rubbing my own throbbing cock which is wet with pre-cum within my panties, against the smooth leather surface of Tom's legs.

Soon I can't wait any longer, so I drop to my knees and begin sucking and licking the clear outline of Tom's hard cock through the tight leather as I fondle his buns from behind. Oooh, the leather tastes and smells so good! And I love the feel of his tight naked ass through the smooth leather.

Tom grips my head from behind and forces his leather covered cock hard against my eager mouth. "You want my cock, don't you, you sexy bitch! Well, you're going to have to beg for it! Tell me how much you want me Bootsie!".

I love having Tom dominate me! It makes me feel so feminine and submissive! I immediately raise my lips from the leather and reply, "Oh Tom, yes lover, I want your lovely cock between my lips. Please let me take it out and suck it lover! I want to suck you and then have you raise the hem of my dress, lower my panties and fuck me!". Standing again, I press my glossy lips against his and give him a deep lustful kiss as I grind my pant and leather clad cock against his and then breathe into his ear, "please lover, let me have your cock now!".

Without waiting for an answer, I drop to my knees and eagerly unzip his pants until his lovely hard cock leaps forward. It's sweet rounded head is oozing pre-cum and I stare at it fascinated, before Tom grips the back of my head and pulls me toward it. "Now show me how much you want me! Suck me!" he cries.

I take first the head of his cock between my glossy lips and swirl my tongue around it and into its crevice, causing Tom to squirm with pleasure. I find that I love the sweet salty taste of the pre-cum and I eagerly begin to bob my head taking as much of his cock in each time as possible. I fondle his leather clad buns as his sweet cock slides slowly in and out of my mouth. I have had my own cock sucked many times by women, but the best blowjobs I have had were given me by the two men I mentioned earlier and I do my best to give Tom the same service.

"Oh yes! Sexy lover, suck me!!!" Tom cries and juts his sweet cock forward. I am now taking about 5 inches of his enormous cock in on each thrust and although I long to take it all, it's just too big! I fondle his lovely hard leather clad buns from behind as I suck him. My own cock is now wet within my panties and squirming against the leather front of my dress, I am so turned on by having this incredible hunk's delicious cock in my mouth!

By the moans that Tom is making, I can tell that he is close to cumming. I try to slow down my sucking and bobbing, but within moments Tom cries out, "I'm going to cum you sexy bitch! Suck me deeper girl!!" His thrusts become more frantic and my jaw is aching and I am close to gagging as I feel the first hot spurts of his cum in my mouth. I eagerly swallow as I feel Tom's whole body arching in ecstasy. "Aaaaggghhh! I'm cumming!" he cries. Tom's body then goes limp as I lick and suck the last remaining sweet drops of cum from his softening cock and then tenderly slip it back into the leather pants and zip them up.

Rising to my feet, I smooth my leather minidress and wrap my arms around him and caress his sweet ass as I press my leather-clad boobs against his hard naked chest. My own cock feels slick and ready to burst within the tight confines of my silk panties and leather dress.

"That was so good, Bootsie! You are some cocksucker!" Tom murmurs while fondling my panty clad buns through the leather of my dress. "I have never had a girl suck me like that before. Do you feel like a woman now?"

I think about his question as I press myself against his lovely and strong man's body. I really have never felt so completely feminine and sexy before. To know that a beautiful hunk like Tom has just had his cock in my mouth makes me feel so sexy and desirable. I reply, "I've dreamed all my life of being with a man like you Tom and I have never felt more like a woman, than when I had your cock between my lips. But I think that I will only feel completely like a woman if I can persuade you to fuck me, and I can feel what a woman does when she has a man's cock inside her". I run my hands over Tom's smooth broad chest and tweak his nipples. "Could I persuade you to put that beautiful cock of your between my virgin buns, lover?"

Tom replies by pulling me to him and giving me another long and lustful kiss. I can feel his cock stirring against mine as he responds, "Oh don't worry Bootsie. I can't wait to fuck that sweet little ass of yours. Let's move to the bed."

I excuse myself for just a moment as Tom stretches out on the bed. Going to the bathroom, I touch up my makeup and reapply fresh lip-gloss. Looking at myself in the mirror, I am thrilled with the realization that I am finally going to lose my virginity to a man and that I feel more feminine than ever before. Smoothing my tight leather dress once more, I re-enter the room and am greeted with the sight of my beautiful bare chested hunk stretched out on the bed and fondling his once again throbbing leather covered cock while he gazes up at himself in the mirror.