First Time Drag

This is my fifth story. I am finally learning how to punctuate (I hope). Hope you enjoy it. Please give me your comments.

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My computer crashed.... again! This time it was worse though, I couldn't reboot, the damn thing wouldn't even restart. I occasionally work out of my home where a working computer is mandatory. I decided to cool off a bit and walked to the local convenience store where I bought two bottles of a dry chilled chardonnay. As I was paying for the wine I happened to glance at a nearby bulletin board. It was filled with various ads like: "Lost Dog", "Gardening Offered", and "Sofa for Sale". One ad immediately caught my eye; it read "Computer Science Student Will Fix Your Computer", beneath that, "Ask for Michael". Multiple telephone tabs were at the bottom of the notice. I tore one loose and headed for home. Once there, I immediately dialed the number, it looked to be a cell phone number.

"Hello," a voice answered.

"Could I please speak to Michael," I said.

"This is Michael."

"My computer has destroyed itself, can you help me?"

"I am between classes right now, but I can come over around six. Is that OK?"

"Great!" I replied finishing the conversation by giving him my address and directions.

I did household chores, cleaned the place up a bit and drank two glasses of the wine as I waited for him to appear. A little after six I heard a car pull up. I looked out the window and saw a cute young man bounce up the walk; he seemed to be full of energy as he moved. He was small maybe 5'6" or so, about 125 pounds. His hair was dark, medium length.

I opened the door as he arrived. "Hi," I said, "My name is Steve."

"Glad to meet you Steve, I'm Michael."

I towered over him as we stood near. I am about 6'3" and 210 pounds; I stay in shape and work out often. I did look quite a bit older than Michael; he was about nineteen or twenty to my forty.

I said, "Would you like a glass of wine?"

He answered, "Not right now, maybe later." He entered and I showed him to my home office. He fooled around with the power buttons and mouse, checked the connections and said, "Bad news, this is probably a hardware problem."

"Do what you have to," I said.

He got to the floor to inspect the main unit; it looked like he was removing the screws to the outer case. As he bent forward, his shirt pulled free of his pants; to my great surprise I could see what appeared to be the thin black strap of a pair of women's panties. I was mesmerized by that simple piece of fabric; I just couldn't help myself and reached out, hooking two of my fingers onto the strap. I pulled the strap out and let it snap back to his hip.

He jumped up and began to stammer, "I, I, I.... you weren't supposed to see that!"

"Calm down," I said. "It's cool. In fact I think it's hot, can you tell me about it?"

"I'd like that glass of wine now." After a long pause he began, "Well, I guess I just like the feel of women's underwear, I like the look and the texture, it kind of turns me on."

I handed Michael a glass of wine and asked, "Have you worn makeup?"

"Well sort of, when I was little, my older sisters would play 'makeup' with me, it was all just in fun though," he continued.

"What about women's clothes, besides the panties?" I asked.

"I have lots of fantasies, but I never had the guts to buy anything other than the panties, I think I could try it though," he answered.

"Give me a moment please," I said as I got up and left the room. I went to my walk-in closet and found the box I was looking for; it was a carton filled with things an ex-girlfriend had left behind. I looked inside and saw several shirts, skirts, shoes, panties and dresses, there was even a zip-lock plastic bag filled with makeup. Everything was clean and neatly stacked; my 'ex' was a neat-nick.

I returned to the office with the box and said, "I have a surprise for you; this is full of women's clothes and things that I think will fit you. They used to belong to an ex-girlfriend who was about your size, will you try some of the things on for me?"

He took a big gulp of wine and said, "Yes, where's the bathroom?"

I picked up the carton and led him to the bathroom. I placed the box on the counter when he said, "Now leave me alone. I'll need some time for this to work." He ushered me out as he closed the door behind me, I could hear the lock click into place.

I drank some more wine as I waited. I was incredibly excited. Well, I waited and waited and waited; one full hour had passed. During that time I could hear water running and things clanking around. I finally said, "Are you OK in there?"

He answered, "Yes, only two more minutes."

Two turned into fifteen when I heard him say, "Could you please close the curtains and dim the lights."

I did as he asked and sat down awaiting his 'presentation'. I heard the bathroom door open and could hear his approach. Into the room walked this beautiful young girl; I mean stunning. Michael had applied the makeup perfectly; his eye shadow was a dark charcoal, his lipstick that deep burgundy that I found so appealing. He had used eyeliner, mascara and probably some of those other mystery things that women apply to themselves. He was wearing a black mini-dress and black suede high-heeled pumps. He was gorgeous, I simply said, "You are beautiful."

He approached on wobbly feet and put his arms around my neck. "Are you sure?"

"Yes," I answered. "I have never seen any woman more beautiful."

"Good, I was so afraid you might laugh."

I hesitated then said, "I want you."

"I want you too," he answered.

I put one arm around his back and the other under his thighs then lifted him up and carried him to my bedroom, he weighed next to nothing. I sat on the edge of the bed and lowered him to my lap. His arms were still around my neck when he began to kiss me; his lips were young and soft, I could feel the texture of the burgundy lipstick. I kissed him back, our kisses growing more passionate. For a moment I actually thought that I was kissing a beautiful, young girl. I slid my hand up 'her' legs, they were smooth; he must have shaved while in the bathroom. I worked my way up those slim, young legs to 'her pussy'. Of course what I encountered was a hard, young cock; that broke my fantasy, but surprisingly made me mad with lust. I had never been with a man before, and I was not even sure that I was with one now. When I stroked his hard cock, he pulled me even closer, kissing me harder. I was tremendously excited. I pulled away and said, "I want to see what your ass looks like in those panties."

He jumped off of my lap and faced away from me, put his hands on his knees and arched his back upwards. I flipped the bottom of the mini-dress to his back to gain a better view. His ass was amazing. It was perfect: young smooth and tan.

He looked over his shoulder and said, "I have a secret place at the dorm where I can sunbathe nude, do you like that?"

"Yes," I cried and began to caress his ass; the cheeks were like no other I had seen. A thin strap of the black panties went up the crack of his ass setting it off perfectly.

He turned around and said, "Will you take your clothes off and get on the bed?"

"Of course," I replied. I took off my faded jeans and polo shirt.

"On your back," he said.

I got on my back. Michael then straddled me, his back to my face, giving me a perfect view of his gorgeous ass.

He said, "Do you have any oil?"

I answered, "Yes, just a moment." I reached into the nightstand and found a bottle of baby oil that I used when I masturbated.

"Put some on your cock," he said.

I did as he asked, my cock glistening with the oil.

He pulled aside his panties and rubbed the tip of my cock against his young hole. He continued, "Don't move, your cock is so big that you might hurt me, let me do it."

He lined everything up and began to push against my cock. First just the head entered, then a bit more. He groaned and continued to move against me. Finally about one-half of my cock was inside of him. The sight was incredible. He slowly moved back and forth, my oiled cock slipping in and out of that young hole.

After a while, he pulled off of me. He got up and went to the bathroom and returned after a bit. He had removed the mini-dress and replaced it with a small black shirt with the word 'sexy' written in bright blue a crossed the front. Standing near me, he removed the panties, his young cock and balls were fully shaven. He got on top of me, this time facing me, and again lowered himself onto my cock. His eyes never left mine; they were a deep brown, the makeup making them seem fuller.

This time, he got almost the entire length of my cock inside. He bent down and hugged his chest to mine. I could feel his hard, young cock between our bellies. He slowly slid up and down while we kissed.

He pulled away from the kiss, a worried look on his face, "I am sorry," he said. His face contorted and I could feel his warm cum squirt between our bodies. "I am so sorry," he continued, tears ran down his face.

My cock was still inside of him. I held his face to mine and laughingly said, "Don't worry little girl. I love it that you came, I hope we can do this again in exactly the same way the next time we make love."

"Sure?"

"Yes, come give 'daddy' a kiss."

He slid up and kissed me lightly. He then got up and went to the bathroom, returning with a few towels. I noticed his makeup had been refreshed and that he was wearing panties. He lovingly wiped me down and then laid a fresh towel on the bed and said, "I want to give you a massage, get on the towel please."

I got on the towel. He squirted oil onto me and gave me a very professional massage, both front and back. He especially paid attention to my feet and ankles, my hands and wrists. While lying on my back, he softly stroked my cock with his oiled hand. He then wiped me down, removing all traces of oil. "I'll be right back," he said and went into the kitchen.

He returned with a bowl of freshly cut fruit. He had me sit up while he fed me slices of ripe pear and sections of mandarin orange, occasionally kissing me between bites. "Are you satisfied?" he asked.

"Well, almost," I answered.

"Silly, I'm only teasing, I want to finish you." He propped two pillows behind my back and said, "I want you to watch me." He took out a tube of lipstick and liberally applied it to his lips then bent down and kissed my chest, stopping to suck on my nipple; his kisses left a trail of lipstick smudges. He got on the bed, between my legs, and began to slowly suck my cock. His eyes were on mine. I could see my hard cock disappear into those beautiful lips; saliva began to drip down my cock, mixing with lipstick residue.

His long warm fingers began to caress my balls and ass. I was getting close; he engulfed me fully and worked the underside of my cock with his tongue. As I watched this act of love, my cock suddenly grew thicker; I was about to cum. He swallowed the entire length of me and held me in place, still staring into my eyes. I began to spurt deep into his throat. He held me like that, never leaving my cock until it began to soften.

He finally pulled his mouth away and said, "Did you like that?"

"Yes, amazing."

He reapplied his lipstick and jumped onto my lap, his arms around my neck.

I asked, "Where do you live?"

"In the dorm, not too far from here at all."

"Do you like it?"

"No, its kind of loud and dirty, and I'm always afraid I'll get caught wearing my panties."

"I want you to come live with me, it's about time I had a girlfriend again. Would you like that?" I asked.

"Yes, yes, yes," he answered as peppered my face with kisses.