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Age when it happend: 18
Where it happened: My House
Sex: Male
Rating: 5
Category: Straight

My first time was very unusual. I ‘ve never done it before and was shy to ask girls out. I am a stellar student at school and bore a reputation of a mummy and teacher’s boy who would never have sex before marriage. I had a lot of Christian friends too, since I was always interested in religion. In one word, I had many obstacles to overcome in order to get laid. But it still happened…

I found out this thing called an escort service.

On a Saturday night, my parents went on a weekend-long trip for their anniversary, and I browsed on the internet. I stumbled across this one 200/hour service where I could ask for all kinds of ladies to give me a good time. I decided I should give sex a try before turning 19. And since I didn’t want people to know that I “broke the code” and had sex, I decided to call up a prostitute.

I called the number.

The agent said Tiffany would arrive in two hours. Those were the longest two hours in my life. I paced around the house, thought about all I used to do to preserve my image of being a good stellar student. I read carefully about sex and since it was going to be my first time, I mentally prepared myself and repeated the procedures again and again. I thought about what wise people said about sex and the first times. I realized I was about to give my most precious to a hooker. Well, since I wanted to keep my identity anonymous, a hooker would be an ideal choice. Right?

The door bell rang.

I knew that my life was about to reach a milestone.

I opened the door–and there stood a girl, no, a woman, you’d only see on television and in movies. Tiffany had curly brown hair and blue eyes–just like I ordered, a spectacular rack and round hip. She was wearing a half-transparent short skirt and was clearly not wearing a bra. The two pieces of cherries were dancing across her bosoms, stealing the attention of every one of my eyes.

I read from somewhere else that escorts don’t like men that come up too quickly, so I saved my initiative to grab her and start kissing her. I gently asked her in, just like I would any girl I respected. “Thank you. Nice house!” Oh–she was a pro–her voice was like the voice of a nightingale, and her smile lightened up the house.

I handed her 300 bucks plus tip (for one and half hour) and we sat on a sofa. I offered her drinks and she made a phone call to the agency to tell them that she arrived OK and everything was about to be taken care of. She crossed her legs–Sharon stone style–I loved it. I was enjoying every moment with her. She was mine–I could stare at her in any way I wanted; I was showing her my lust from every grin I sent off and every word I said. My hands were actually trembling because i was nervous about my first time. She clearly could tell.

We got the talking going. She was so nice. Like my grade school teacher. Except a lot sexier and a lot more generous in giving you sexual favors. So I told her that I was a stellar student (not disclosing my age) and that I didn’t want to fk a girl b/c that would ruin the image I put up for everyone else. She sympathized with me, moved closer to me on the sofa and caressed my arms. She was like a springboard that I could say anything to. It didn’t matter if she really cared. All I wanted is to tell her stuff I couldn’t tell anyone else. She just sat there and concentrated on what I had to say. Once in a while she’d be like ” I totally agree” or “That must have been difficult.” I didn’t care. I just talked.

As I was talking, she caressed my arms, my ears and then my lips. Then I had to stop talking b/c her hands were on my lips. I was like “O God here it goes. Get lucky~” Then she asked if I wanted to “get comfortable.” I read from somewhere else what that meant, and I am sure you do too. I immediately said “yes, ma’am. At your service.” She laughed, coz it was so ironic.

I liked the fact that I made her laugh. I mean what’s wierd about me is that I want to have sex, but I also respect my partner. I want them to be happy. That way both of us enjoy the sex, and my first time would be a perfect one.

I felt her hand that was on my lips and put it on my chest. I let in unbottoned my shirt and moved it to my lower body. I said, “How would you like to handle a stick? You can be my driver.” She laughed again, this time even louder. She willingly ran her hand gently across my cock–which was already hard–and applied pressure evenly on the surface of my balls. I was joyous. I could literally see angels dance infront of my eyes. I was in heaven–come on, I never got a hand job before–this felt really really great.

I took off my shirt, and said, “How would you like to eat a human hot dog?” She smiled mildly and helped me unzip my pants. My underwear was already a little wet–I guess bc of the pre-action. She rolled my pants to my ankles and slowly, inch by inch, skinned my underwear. I felt time had frozen there. I was like a stone. I was about to be sucked. Then her lips met my cock. Her tongue ran all over its round surface and I started breathing harder and harder. She looked at me submissively once in a while to make sure her client was well served. I never felt that way in my life before–I excelled in school, was loved by my parents, and enjoyed every little achievement I ever received–but that feeling of getting sucked was strangely, disturbingly, and exponentially better than any of the aforementioned. I felt that a part of me was finally working. It finally found its godamn purpose. I was like, “FK yeah!!”

Then it was about 20 minutes into the service. Too bad time passed so quickly. It was time for the premium service, I guess. She sucked me well and then let me get naked completely. I was like Adam before the Garden of Eden issue, and I asked her to become my Eve. I asked her if I could help her undress. She nodded with a smile. Then I came up with a better idea–I read from somewhere that you get a better experience when your girl “trusts” you. To do this she has to “know” you are a good guy first.

I offered her a massage.

I didn’t have a long cock; I wasn’t a pimp at school; I wore thick glasses and partied 10 times less than my friends.

But I am hell of a massuse. Don’t remember how I got that.

I let her lay on her stomach on my bed and gave a full-body massage. I lay my hands on her shoulders first and slowly caressed her, like pampering a little sheep. I was so gentle that she started moaning. She was like, “You are such a gentle client. I’ve never met anyone like you before. You must have had a lot of experiences with girls.” I was surprised she’d say that. I guess I am just wierd like that. I learn a lot about having sex, but never really get around doing it. shoulders, then neck, back, and her butt. I placed both palms gently on the two cheeks and squeezed carefully, like I was squeezing for juice but didn’t want the juice to spill all over. My hands felt like I just got an electric shock when I squeezed that ass. O my gosh–God be blessed himself–who would know He could create a pair of objects that made you feel so good.

Then I decided it was the end of being a gentleman. I wrapped my arms around her posterior and started touching her pussy. It was already wet, and she seemed to like the way I worked inside her. She started giggling, like a little girl who got complimented by her little boyfriend. Then I carried her and flipped her around, gentlemanly. Man she weighed at most 50 pounds! My hands slided across her body from bottom up, all the way to her breasts. The two hills were still covered in her purple dress. They were till shy to be unveiled. I unbuttoned her dress and saw her bosom–white like snow, or like whip cream with two strawberries sitting on top. Oh my Gosh! Another wonderous creation of God! I instinctively leaned over and sucked the tits, one at a time. She must have put scent on them–they tasted so good. I licked both of them with higher frequencies–she was groaning and moaning.

I couldn’t wait any more. I was about to come.

I let her take off the top completely, and took off her jeans. Her purple underwear was the last obstacle to my victory–or loss, of my virginity. I pulled them off slowly and saw her beautiful pussy, waiting to be penetrated.

It was time. My dick was so hard that I went in without a problem. Then time froze. I felt I was at the peak of my life; not only my life; I was at the peak of the history of men; I was at the top of humanity of all times, all spaces and all fking continuums. I just found gold. I was just loved. I saw flowers. I saw a land full of flowers. I was in. O that felt so fking good! My partner moaned in a pleasant pain. She was being fked, I know. But she liked it. She wanted to be fked. Holes would be filled. Pussied needed to be penetrated.

I moved up and down, left and right. My hands grabbed her tits and rubbed every part of her body. My lips kissed her face, hair, ears, mouth and everywhere I could find. I was only concentrating on my dick though–for that was the command center of joy.

O my gosh it was so good. Now I understand why in movies people blank at the ceiling feeling so proud after sex. It was like a battle won. It was like a title claimed. It was like a position rewarded–I BECAME A MAN!

Then the wierdest thing happened. She seemed to start feeling more and more painful, and started punching my face with her fist. She was weak but the punches were still hard. “Stop it, btch” I said. But she wouldn’t. Then I tried to go in further, but all of a sudden her pussy seemed to have disappeared. What the fk?

Then I opened my eyes. My dad was tapping my forehead to wake me up. There was sun outside. Another school day and I was about to be late. Goddam it. “Get up dude!” Dad said.

Fuck. That wasn’t real? That felt so fucking good! I wish all this could come true someday, mf’s.

“Alright alright I am up. I need to shower first though.” I felt the quilt and my underwear, which were both had a big wet spot on them.

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