Girl for Charlie

Story Info
Unexpected gay visitor gives him a chance to dress up.
2.7k words
4.59
88.1k
81

Part 1 of the 2 part series

Updated 10/30/2022
Created 12/28/2012
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My girlfriend was away for the week, visiting family back east. I had the house to myself and intended to make the most of it. Shelley is 26, 5' 7" a brunette with a great figure, she's fun, sexy and hardworking. We have been an item for three years and living together for almost two.

I was in our bedroom getting dressed up having had a long soak in the tub full of bubbles with two martinis and a couple of joints. I had chosen what to wear from Shelley's large closet in the bedroom. I'm only 1 inch taller than her and 155lbs, so most of her clothes fit me. I was wearing red satin and lace low rise boy short panties and bodice and black hold-up stockings. I had painted my nails, shaved all of my body hair away, leaving only a neat triangle of pubic hair and had just sat at the dressing table to tackle my hair and makeup.

The phone had rung twice while I was indulging myself in the tub, but I had ignored it. I had already said goodnight to Shelley who was three hours ahead in DC. I was relaxed, music on the stereo, sex in my mind, porn on the TV in the bedroom beside me. Nothing but an evening of solitary queenly pleasure on my mind when I heard a car pull up.

I froze. Who could it be? Enough lights were on in the house to give my presence away. I peeked outside through the curtains and saw Shelley's friend Charlie lifting an enormous canvas out of the back of his SUV. He looked up and saw me. He grinned and pointed at the canvas as he headed towards our front door. Thankful that I had only just done my hair and started with eyeliner, "He won't notice that little bit" I thought. I pulled on sweat pants and a big baggy sweatshirt. All of my male clothes were put away for the weekend. The sweats I grabbed were snug stretch lycra and hot pink. The hooded sweatshirt was baggy but short and pink with a Betty Boop logo.

My heart pounding, I went to the door, mussing up my gelled hair, thinking of a suitable excuse for the sweats. I opened the door and in swept Charlie. "Hello gorgeous," he crooned. "Sorry to drop it off early, but the thought of it sitting in my car all weekend is more than I can bear."

"She should go here, I think," he said. Lifting a landscape off the hook above the fireplace.

"Well, unwrap her then!" he said, turning to face me. He drank me in with one long appraising look. "Ohhh, look at you.... Shelley's gone, you're missing her!"

"Uh, yeah," I said nervously , beginning to tear off the brown paper and bubble wrap.

He was a 6'3" handsome gay art dealer, 12 years older than me. A friend of Shelley's from college. He made a great living doing what he loved. We always had a great time with his overtly friendly very slightly camp character but I always felt a little upstaged by him. Tonight, caught this much off guard, I felt nervous and absurdly timid.

"Wow!" I exclaimed as I pulled the painting free of its covering. A reclining nude vaguely resembling Shelley lay on a chaise, eyes closed.

"Isn't she gorgeous?"

"Completely."

"You can't keep her, she's one of a pair, but until I find a buyer, she's yours." He lifted her up onto the hook.

"I'm not sure the living room is the right place for her."

"I know what you mean, her boyfriend has pride of place on my bedroom wall!" He gave me a grin as he came back to stand beside me looking at the portrait. "Yum."

He put his arm amicably around my shoulders as he leaned beside me. My heart was pounding, for the first time in three years of knowing him I saw him as an attractive and sexy man and his hints at how sexy he found me were now not falling on deaf ears. My head was in utter confusion. Was it just because of what I was wearing under my sweats and the evening of pampering myself?

My thoughts all evening had been focused on what it would feel like to be with a strong male lover. Charlie's hand was gently stroking my shoulder. My primed body was responding with a will of its own. His fingers found the spaghetti strap under the sweatshirt. I felt myself freeze. His fingers played with it a little and I felt a roaring in my ears.

"Mmmmm." He was looking down at me.

"Look, this isn't .."

"Shhhh" he said, pressing a finger to my lips. "I see you've been fixing martinis. Why don't you make me one."

I looked up at him, his face leaning down into mine. His hands stroked down my back and over my tightly clad buttocks. Cupping them, he drew me against him. He almost kissed me, his breath hot on my lips and I was going to let him, but he pulled back leaving me wanting his kiss and the smirk on his face showed he knew it.

"Time for me to open MY present," he said, his hands unzipping my sweatshirt, slipping it off my shoulders.

"Please, no" I whimpered, but more from embarrassment than lack of will.

The sweatshirt came off leaving me in the boned bodice. "Even better than the painting." he said standing back, eyeing me up and down. "Now for my Martini".

He turned me around and patted me on my butt to send me on my way.

Sheepishly I walked over to the kitchen bar, feeling his eyes on me all the way. "You are so damned cute." he called after me. It made me blush anew but gave me an unexpected lift.

He chatted away as he walked around the living room, picking things up, nosing around in his usual friendly way. I made us each a martini and downed a shot of vodka to give me the resolve to face Charlie anew.

"These are cute" he said, walking over to me holding the pair of high heels I had bought for myself on the way home for work. "They'll show off those pretty pink toenails of yours. And your ass is going to look even sexier"

My heart lurched back up into my throat. Did the man see everything? He was grinning at me, the silver 4" heels hanging from his fingers.

He chuckled "you look so cute with that deer in the headlights look".

This was too much! I grabbed for the vodka bottle.

"Woah, there cutestuff. Slow down."

"Look, Shelley doesn't know anything about this side of me and she would be devastated if she found out"

"Stop worrying. Your secret is safe with me. What she doesn't know won't hurt her" he replied

I was so relieved, I felt a little giddy. "Oh, Thanks, Charlie. I'll owe you one"

"Yes, you will," he said with clear innuendo. "The way I see it, I could stay or leave. I 'm on my way to a party where I am guaranteed to get laid but it does seem a shame to leave you to party all alone. Especially since you are looking hotter than ever and showing such potential. I'm off to the bathroom then perhaps you can show me your gratitude before I leave by showing me what you have hidden under those sweats." His hand caressed across my ass as he turned and left.

My heart was pounding. I was thrilled by his touch and thrilled by his compliments and intrigued by his offer to spend the evening with me. What the hell, time to take the plunge. I headed upstairs with my heels in hand and rushed to the dressing table. I fluffed the life back into my hair, applied mascara, blush and lip gloss as fast as I could, slipped out of the sweats and into a red satin flared miniskirt and sheer see-through black blouse.

Sometime during it all I heard the toilet flush and I started hoping he wouldn't leave just yet. I buckled the sandals and headed for the stairs. I stopped at the top and took a deep breath, trying to calm down. I gingerly walked downstairs, careful not to trip.

He was sitting in an armchair with his back to me, but turned as soon a he heard the click of my heels on the hardwood floor.

"My, oh my. What a delightful sight you make."

I was shaking as I walked over to him. I stopped just in front of him and did a twirl.

"Oh, you sexy thing!" He said with unguarded appreciation.

It gave me the boost I needed to say what I had to say. "Thank you, sir, for keeping my secret. If you would like to stay a while, I will show you the depth of my gratitude. I'm very new to all this but if you would teach me I want to learn how a girl feels in the hands of a lover."

Charlie's eyes were roaming all over me as I spoke. He handed his empty glass to me and grinned as he answered. "I need another martini. Why don't you fix me one while I consider your offer." The arrogant way he dismissed me let me know he was enjoying our theatrics.

"I was right about those shoes" he called after me, his eyes obviously still on me. I gave my walk a little more wiggle and he called "Oh, yeah baby!"

I was alive and thrilling with the possibilities as I made yet another martini. This was going to be fun. This handsome experienced guy knew his way around the gay world and gay sex and he liked me enough (even straight) to be my friend. Excited and nervous about what the rest of the evening had in store, I sashayed back to him, a martini in each hand.

He ran his hands up my stocking clad legs. They slipped up under my skirt and caressing my ass, he said "I'll stay with you for the evening. I'll let you know right now though, I aim to make this so good that you keep coming back to me for more. Now sit in my lap sweetie and lets talk about rules."

"Good girl," he said as I complied.

"First. I like you calling me Sir, either Sir or Charlie will do, sweetie, but use them in everything you say." His hands were roaming over me, one over my neck and shoulders the other on my legs. His mouth at my ear, his breath delicious on my skin as he spoke.

"Yes, Sir"

"Second. I am clean, I recently had tests, If you are not Ok with that or if you aren't clean, one of us needs to get my condoms out of the car." His mouth was hovering over mine.

"I'm ok, Sir" I whispered as he kissed me, his hands driving my body wild with their soft caresses. His tongue parted my lips and I moaned involuntarily as he danced in my mouth. I'd never been with anyone who had done this. The newness was amazingly thrilling.

He lifted off my mouth. "Third... This...," he said purposefully stroking the length of my arousal through the thin satin panties "beautiful though it certainly feels, is not going inside anywhere. Your satisfaction will come from satisfying me and from my hand."

"Yes, Sir." I moaned into his rapidly descending mouth. This time my mouth was already open for him and eagerly accepted his kiss. His tongue driving repeatedly into me sending my mind into a whirl. My arms went around him, my hand playing in his thick curly hair. His hand stroking me, driving me wild. I was so turned on my hips writhed up to meet him. The sensations were overwhelming me and I felt myself surrendering to his mastery of me. My body started to jerk under his unrelenting onslaught. I was moaning onto his hot mouth continually riding the wave towards orgasm.

Something clicked in my mind and I dragged my mouth away from his. I buried my face in his neck as I pulled his hand out of my lap.

"Please, Charlie. If I cum, I'll sober up way too much. Tease me all you want, just don't let me cum 'til you've finished with me."

"Hmmm," he chuckled "Good girl. Honesty is good. Could be a long wait for you though....I intend to take my time"

"Good. I want it to last, Charlie. I want you to show me how...." He silenced me with another ravishing kiss. His hand in my hair holding me tight to his relentless mouth, his tongue playing deep with mine. His hand rolled out of my grasp and again stroked my aching flesh. I moaned, knowing I was powerless to stop him, all my resolve disappearing in a wave of desperate lust.

Just as quickly his hand left me, before I knew what was happening I was gasping and he was laughing. "Oh, this is going to be so much fun, you want it so bad, don't you sweetie?"

"Yes, Sir" I whimpered.

He took hold of my hand and placed it in his lap. His cock was hard as iron inside his chinos. My hand automatically went around it, starting to caress and stroke it through the fabric.

"See how much I enjoy you?"

"Yes, Sir"

"Get up"

He spread his legs apart then had me kneel between them. "Take my cock out. Be gentle."

I unzipped him and unbuckled his pants. I opened his boxers and was rewarded with the long thick shaft of his penis, thick and hard in my hands. I caressed it and stroked it, mesmerized by its heat and size and how silky smooth and soft it felt on the outside when it was so incredibly rigid. My fingers stroked the length of it, grasped it and massaged it. I loved it, it was a wonderful feeling, making him feel good.

I heard a moan from him as in dipped my head. I looked up at his approval as I took my first cock into my mouth. It filled my mouth, stretching my jaw. It filled my senses and I closed my eyes, loosing myself to the thrills that were charging through me. I bobbed my mouth up and down on the hot swollen head. I swirled my tongue over it.

"Yeah, love on my cock, sweetie. I'll make you my girl"

I was overwhelmed by my desire for his cock, caressing it with my tongue, kissing it with my lips. I was greedy for it, taking more and more of the length deeper and deeper into my mouth with each stroke. Moving faster and faster as Charlie's hips moved to meet me. His hands were in my hair, caressing me, urging me.

I looked up at him and his eyes locked on me. Lust filled and powerful he looked down on me as I took his big hard cock again and again through my hungry lips.

"Oh, you love sucking my cock, don't you! You want to be my girl! You want to take my cum!" He sees it all in my desperate greedy eyes.

I closed my eyes feeling his hips thrusting up with increasing urgency until I felt his cock swell further and pulse. Then my mouth was filling with hot jets of creamy salty cum. Greedily I swallowed all I could, pumping my lips down his shaft as I listened to him moan "Yes, yes. Bitch , swallow my cum" . Then I eased off, suckling and kissing and licking his cock, not wasting a drop, my eyes looking at his face for approval.

He groaned "Oh, yeah. You did it, sweetie. Oh you are my beautiful little girl." He drew me up to him and dipped his head to kiss me deeply again. I received his kiss wantonly, delighted by the thought of the pleasure I had given him, loving the sour aftertaste of his cum and what it meant for me.

His hand slipped down between us and he stroked me. I was very aroused and he lifted his mouth from mine and said "looks like someone is enjoying herself, perhaps we ought to go upstairs and play some more."

Why not? I thought to myself. I really want this.

I stood up, taking his hand and wordlessly led him up to our bedroom.

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16 Comments
lingerie65lingerie65over 5 years ago
Keeping my secret

Such a hot and luscious story, that it blew wind up my skirt. As I became the girl of the house when my girl left to visit her parents once I'm on my back with muy legs spread & I'm impaled (I'll become the woman of the house) by his meaty shaft.

pamcdpamcdalmost 6 years ago
Mmmmmmmm

I like the way everything is played out. Now for hot fun sex.

AnonymousAnonymousover 7 years ago
I love dressing for gay men

I too love cross-dressing for gay men, even more than straight or bi men. They really appreciate the effort I make in getting all sexy for them. They also kiss much better than bi men. I love sucking cock and getting fucked. This story of yours has happened to me quite a few times. I can't wait to read the next chapter and many more.

AnonymousAnonymousover 8 years ago
my gay lover

Wonderful story of how a man becomes a sissy slut for a hot studly gay man. That's what I've become and I love it. I can't wait to read the next chapter.

goodlorigoodloriover 10 years ago
Oh Yes

More pleasssseeee

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