First Time With My Best Friend Ch. 01

My friend John is really sexy. He is tall and blond with a lean strong body. I have often imagined what it would be like to have his sweet cock between my lips, or between my virgin buns. He’s too good a friend though, and I’ve never had him give me any hint that he might like to be with a guy...

One night my best friend John comes over to my house on a hot summer night. John is really sexy. He is tall and blond with a lean strong body. I had often imagined what it would be like to have his sweet cock between my lips, or between my virgin buns. He’s too good a friend though, and I’ve never had him give me any hint that he might like to be with a guy.

Tonight, he is dressed in a T-shirt and tight shorts which reveal his firm tight buns. He looks tanned and beautiful! I greet him at the door wearing a similar outfit. The only difference is that underneath my tight shorts I have on a pair of sexy pink silk bikini panties, which hug my swelling cock as I shake John’s hand and run my eyes over his hot body. They feel so delicious and silky soft encasing my sensitive skin and rubbing against the front of my shorts.

We drink some beer and have a good time and then I suggest that we go skinny dipping in the pool. This is not a new suggestion for me. I always enjoy the site of John removing his clothes and revealing that gorgeous lean and muscular body. Tonight as he slips out of his shorts and his sweet cock comes into view surrounded by blond curly pubic hair I long to take him into my mouth and suck that beautiful cock. Of course I am always careful not to reveal my lust.

After we swim John asks if its ok if he spends the night because he’s too tired to drive home. I say “sure”, and we go to my bedroom where he slips naked into bed and says goodnight.

I am so turned on and hot for him but I dare not act on my desire. Going into the bathroom I decide to dress up and fantasize that I am doing it to prepare for John. I slip into a pair of sexy silk bikini panties and a matching pink bra. I then put on a frilly satin and lace white garter belt and attach it to sheer white stockings, which I roll up my long and muscular legs. Slipping my silicone boobs into my bra, I apply glossy pink lip-gloss to my full lips. I feel so sexy and feminine; my cock is straining against my panties as I imagine myself pressing against his hard body. I decide to go a bit further and I pull out my ultra sexy black thigh high boots. Slipping them over my satiny stocking clad legs is such a turn on. They hug my legs tightly as I zip them up. The soft calfskin leather feels so wonderful and the smell of leather always gets me excited. I begin to fondle my panty-clad cock as I dream of wrapping my boots around John’s waist as he fucks me when suddenly a daring thought comes to me. I decide to slip in the dark, into my room and under the sheets next to John’s sweet sleeping body. I’ll take some tissue with me so that I can gently and slowly masturbate while close enough to feel the heat of his sleeping body.

I hear no sound as I slip into the room. As I slip under the cool sheets I take care to leave some distance from John. The soft silkiness of my panty clad buns and my satiny bra against the cool sheets is thrilling as I slip under the sheet. I lay there, the sheet rising over my jutting boobs and the pointed tips of my sexy boots. I feel so sexy and horny as I begin to imagine what it would be like to reach out and stroke his hard muscular chest, to squeeze his nipples and fondle his sweet cock. My own cock is throbbing as it strains against my sexy silk panties. Reaching slowly down I begin to fondle it.

It is so incredibly exciting to be so close to John while dressed in forbidden feminine lingerie. I am so hot that if I were alone I would have reached my climax by now. But because I have to be so careful to be quiet and not wake John, I am becoming ever more turned on, perhaps more than I ever have been. I begin to slowly rub my boots against one another and I have to take care as my tight panty clad buns begin to squirm. Suddenly I freeze as John says, in a voice with no trace of sleepiness, “boy, Nancy looked so foxy today. I would really like to get inside her panties, wouldn’t you?”

I am so shocked and scared for a moment with the blood rushing to my cheeks that it takes me a moment to respond. Racing through my head is the question, “If he was awake this whole time, has he noticed the sound of my stocking clad legs sliding along the sheets? Has he heard my panting breath as I imagined being in his strong arms and I fondled my panty covered cock? Can he smell the leather of my boots or the cosmetic odor of my lipgloss? Is it light enough in here for him to notice the sheet riding up over my jutting boobs, or my hand that even now is gripping my shrinking cock?”

The answer to his question is simple. Nancy is indeed a fox. She has a gorgeous sexy body with a voice and face to match it and she is always dressing in leather miniskirts. I often dream of what her panties and bra must look like and I would love to fuck her. So it is not hard even at this scary moment for me to say, albeit with maybe a hint of a tremble in my voice, “oh yeah! She is fine! I would love to undress her!”

To my horror as I glance to the side, I can clearly see the silhouette of John’s lovely body. If he has looked at me, I am sure he has seen what appears to be the figure of a woman lying next to him. Raising my arms I hastily cross them over my bra in an effort to obscure my bust line. I also try to lower the tips of my boots but, to my horror, they rub against each other making that distinctive leather squeak. I lay there petrified, my cheeks burning as I wait for him to speak.

“Me too! She wears some sexy clothes, doesn’t she? I love seeing her in that tight leather miniskirt she wears! And those boots! Have you seen her in those sexy leather high-heeled boots? John asks.

Lying there I begin to relax a little as John goes on and on about sexy Nancy. As he talks about her sexy clothes I begin to relate as these are the things that I also focus on. My cock begins to swell within my panties as I hear John talking about leather miniskirts and boots. I sometimes wish I really were a girl like Nancy and gorgeous hunks like John would lust over me.

“Yeah I love those boots and that skirt.” I respond. Little does he know (I think) that I’m wearing an even sexier pair of boots as we speak, or that I have two leather miniskirts in my closet!

“I often fantasize about Nancy. I wonder if she wears a garter belt with those lacy stockings she is always wearing. I love to see pictures of girls in garter belts and sexy lingerie. The bummer is that none of my girlfriends ever wear lingerie like that. Wouldn’t you love to be with a woman dressed in a sexy garter belt and stockings and thigh high leather boots?”

By this time my cock is fully erect and throbbing against my tight silk panties as I realize that he must know what I’m wearing and is making a point of telling me that it turns him on. It takes an effort for me not to reach down and fondle my panty-clad cock and the sides of my frilly lace garterbelt. Suddenly, I notice that the bed has begun to shake somewhat and looking over I see in the dim light that John is stroking under the sheets what appears to be an enormous cock by the looks of it.

I want so much to lean over and take that cock between my lips but I want to make sure I’ll be welcome. “You’re right John. There’s nothing like the site of a woman dressed in sexy lingerie. I love the feel of silky panties and bras. Satiny garter belts with lace trim and silky negligees. And the smell and feel of leather boots is so exciting!”

“Oh yeah! You’re so right!” He exclaims as he lowers the sheet and I can now more clearly see the outline of his enormous cock as he strokes it slowly up and down. It must be 9” at least! “I would love to be with someone dressed like that!” He says.

I need no more encouragement, getting up on my knees and leaning over him I wrap my hand around the base of his throbbing cock. “let me help you with that John” I coo as I begin stroking his sweet cock. “It feels better doesn’t it when someone else does it?”

“Oh yes! That feels wonderful! Grip me tighter Jamie! I have never had a guy handle my cock before. It feels great!”

Encouraged by this I lean on and slip my glossy lips over his oozing cock. I am n heaven! I have dreamed of this and it is even more exciting than I imagined it could be. John moans in delight and I raise my head and ask “ and how does it feel to have a guy’s lips around your cock?”

“Oh Jamie lover, don’t stop! Your lips feel so wonderful around my cock. I’ve always wanted a blowjob. This is my first!”

Taking his hand I guide it to my own panty covered throbbing cock. As he grips it he exclaims, “what are you wearing?”

I feel a sense of shock. I was sure that he knew how I was dressed and that was why he was talking about lingerie. I suddenly realize just how daring I have been. I reach for the light and as it comes on I am revealed to him with my male muscular body that he has seen so often clad in feminine sexy clothes and boobs jutting forth within my bra. “You said you wanted to be with someone dressed in sexy lingerie and a garterbelt. Does it matter that it’s me?” As I ask him this I continue to stroke his cock. I want to keep him excited so that he doesn’t dwell on the fact that this friend that he thought he knew so well has a secret other, feminine self.

John stammers a bit as he says, “I just had no idea!”

“Don’t think about it John. Just lay back and close your eyes and imagine that I’m Nancy”. Leaning forward I wrap my lips again about his sweet cock and slowly slide my lips down until I have taken more than half of it in. It is too long for me to take all of it so I begin sliding it in and out, taking as much in as I can each time. Looking up I see that he has closed his eyes and he is moaning in excitement.

Letting his cock slip from my mouth again I straddle him and pressing my panty covered cock against his and my leather boots along his, I murmur, “doesn’t that feel good lover, your cock pressing against my panties? I love the feel of silk against my cock”.

“It does feel wonderful Jamie”.

Taking his hands from his sides I place them on my garterbelt-covered hips and then urge them up along my muscular hard belly until he is fondling my soft silicone boobs through my satin bra. “Call me Nancy. Imagine that I’m Nancy and these are her panties you’re feeling and her garter belt and bra”.

Leaning down I take his hard left nipple between my glossy lips and begin sucking and nibbling it as I tweak the other one between my fingertips.

“Oh yes Nancy! I love that!” he says as he starts to grind his cock against mine.

I then begin to kiss and suckle my way up his broad hard chest to his neck as I murmur, “imagine that these are Nancy’s lips now and Nancy’s tongue”. And with that I press my glossy lips against his and slip my tongue into his mouth. He responds immediately swirling his own sweet tongue against mine. Our kiss grows ever more passionate as I lay my body over John’s and we squirm against each other. His hands are now roaming, gripping my hard panty covered buns and then my muscular smooth sides and my bra strap.

John then grips my sides and rolls us over. I guess that he wants to be in the dominant position as he usually is with his girlfriends. I wrap my booted legs around his waist and his cock wedges itself between my panty-clad buns and as we continue our hot kiss he strokes his cock back and forth. I have never had a cock up my ass, but I have often dreamed of it and the feel of his sweet cock pressing against my anus is incredibly exciting.

Breaking our kiss I ask, “John I want you to fuck me! Please lower my panties and fuck me with that gorgeous cock of yours. Please lover!”

Opening his eyes he looks at me and asks, “Have you ever done this”?

“You’re the first man I’ve ever been with John, believe it or not. And you know I like being with women. But I have long fantasized about being with a guy. In fact, the reason I’m dressed like this lying next to you is that I thought you were sleeping and that I could lie next to you and jerk off while dreaming that I could be in your arms like I am now. Every time I dress up like a girl I fantasize about what a girl must feel when she has a man’s cock inside her. Please John, treat me like a real girl. Show me what it’s really like!”

John doesn’t seem to have any more reservations as he grips my head, presses his lips against mine, and forces his hot tongue into my mouth again in another passionate kiss. Reaching down he grips my panty-clad buns tightly and angles his cock so that it is pressing directly against my virgin anus through my panties. “Ok lover, I’m ready to fuck you like a girl!” With that he grips the sides of my bikini panties and slides them down to the tops of my thigh high boots.

“Wait just a moment John. I think we better put some KY jelly on your cock so that you slip in easily”. Slipping out from under him I open my bedside drawer where I keep a dildo and some KY jelly. I spread it liberally over his quivering cock and slip a little around and in my anus with my finger. Rolling over onto my back I announce that I’m ready. Raising my booted legs I rest them on John’s shoulders as he presses his quivering cock against my the entrance to my virgin, but eager ass hole.

“Slip it in lover! Slip it slowly in!” He requires no further urging. As he grips the top of my booted thighs for leverage, he begins to gradually slip his gorgeous cock into me.

“Oooh yes John! Deeper lover, deeper!” I cry as my rectum fills with his giant cock. My dildo is 7” long and I have often practiced with it while dreaming of having a real man inside me. But, John’s sweet cock is at least 2” longer and definitely thicker and I have never felt so filled as he stretches me until I have absorbed all of his luscious cock. I am a little afraid of what it may feel like when he starts to move. “Slowly lover, fuck me slowly at first until I get used to your big cock!”

“Oh Nancy, you feel so tight and wonderful! I love the feel of my cock in your ass! I’ve never felt anything like it”. He begins to slowly withdraw he has almost slipped out and I am dying for that feeling of fulfillment so I grip his hard buns and pull him back all the way into me. He begins to fuck me in and out, slowly and steadily. I grip him as tightly as possible and my ass wriggles with excitement. My hands roam from his sweet hard buns to his hard and muscular chest and his erect nipples, which I squeeze and fondle as he moans with pleasure.

“Faster lover, faster and harder! Fuck me you sexy man!” I urge him on with my booted legs, which are wrapped behind his head. I have never felt anything like this…so incredibly filled and excited. My own cock is hard as a rock and it takes all my will power not to fondle it because I know I would cum instantly.

Now John is slamming his cock hard and fast into me and I can feel his body tense as his cock begins to spew its warm milky load into my rectum. “Aaagghhh! Oh yes Nancy!” he cries before slumping forward down onto me. I unwrap my boots from his shoulders and wrap them instead around the back of his legs as his cock softens and slips from my ass. Wrapping my arms around him, I feel so incredibly feminine and satisfied, like a real girl who has just been fucked by a gorgeous hunk. His weight on top of me feels so good against my boobs and my still throbbing cock.

To be continued…