A Planned Surprise

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I fulfill a long time fantasy.
1.2k words
4.17
43.8k
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I didn't realize how nervous I was until half way through the hotel lobby when I felt my hands shaking. As I pressed the button to call the elevator, I thought about turning back, but before I could, the elevator showed up and I found myself stepping on and pressing the button for the 14th floor. The elevator didn't stop on the way up, and when the door opened on the 14th floor I hesitated briefly before stepping out into the hall.

The sign said room 1412 was to the left, so I went to the left. At the end of the hall, in the corner of the floor was room 1412. I breathed in and out a few times before knocking gently on the door. It seemed like an hour before she opened up, but it couldn't have been more than a few seconds. Ashley looked just as she had in the photos she sent me. She was tall, at least 5' 7", with shoulder length blond hair, blue eyes, tan skin and she was in great shape. She had curves in all the right places and her makeup was flawless.

I had been extremely specific on what she should wear, and she didn't disappoint. I looked her up and down, taking in the white button up tank top that showed off a yellow lace bra and lots of cleavage. She was wearing a black skirt that came down to the middle of her thighs, but flared out instead of being tight. She had thigh high white stockings and high heels on. She smiled at me, and asked me to come in.

"You look amazing, Ashley," I said.

She smiled again, and thanked me as she shut the door behind me. My heart was hammering in my chest as she walked towards me, and before I could say anything else she kissed me, softly. I moaned into her mouth and kissed her back. Our tongues danced together between our lips. I found myself groping and feeling her body as we kissed, and she didn't stop me. I was touching her shoulders, her neck, her back. I let my hand wander down to her ass, and felt how firm it was. She had told me she worked out, and the result was a perfect body.

I broke my lips from hers and started kissing her neck, and at the same time I found the top button on her shirt. As I kissed my way down her neck onto her chest, I unbuttoned her shirt all the way down. I paused for a moment to take it in, her ample bosom was moving up and down behind the yellow lace bra, and she was breathing heavy. Her skin was flush, she must have been turned on. I took her shirt off leaving her in her bra and skirt, and I continued kissing her chest. I unhooked her bra and took it off, giving me my first glimpse of her perky tits. I guessed a 34C; they were perfectly shaped and tanned. Her small nipples had dark brown areolas, and were completely erect.

She moaned as I took her nipple in my mouth and sucked hard. I knew from our communications that she loved having her nipples sucked on. I teased the other nipple with my fingers for a few minutes while I sucked away. After a while I straightened back up and kissed her hard on the mouth. She hungrily kissed me back and asked me to take off my clothes. I obliged and felt her hands moving around my body, but never touching my rock hard cock.

As we continued to make out, I moved my hands down to her waste, and finally to her ass. I reached under her skirt and found she was wearing a thong, just as I had requested. I wasted no time in moving my hands up her ass to the top of her thong, and as I gripped the elastic band and started pulling them down I knew that I was going to get what I wanted, what I so desperately needed.

I slid her thong down and as it got to the bottom of her ass cheeks, I felt her cock spring out from where it had been hiding. I had never been so excited in my life. Her thong dropped to the floor and she stepped out of it as my left hand wandered from her ass to her front. I found her cock with my left hand, it was hairless, and semi hard, but at the same time it was very soft. I wasted no time and kissed my way down her chest, to her stomach as I dropped to my knees, stroking her cock slowly as I did so.

I lifted her skirt and looked at a cock besides my own for the first time in my life. It was hard to tell how big it was, but it looked bigger than mine. She was obviously turned on, but her cock wasn't at full attention yet. I licked the tip and tasted a bit of pre-cum. That was all I needed and I hungrily put my mouth around her cock. It was still mostly soft, and I started massaging it with my tongue and lips, begging it to harden in my mouth. I was playing with her balls as I did this and it didn't take long before she was stiffening up in my mouth.

As soon as she was fully erect, I let it fall out of my mouth and I licked it from base to tip, and sucked on each of her balls for a few seconds. Then I kissed the tip again before putting it in my mouth as deep as I could. I had dreamt about this moment for as long as I could remember, and it was finally happening. I tried to think back to all the blow jobs I'd gotten over the years, and applied the best techniques used on me to Ashley's cock. I was sucking and stroking her cock and it was seemingly getting harder and harder. My jaw was starting to hurt, but I knew I couldn't stop. I had to make her cum. I lightly probed a finger into her asshole, while I continued to suck and use my lips on her cock. Just as I thought I could take no more, I felt her cock convulse, and her asshole pucker as she shot spurt after spurt of hot salty cum into my mouth and throat.

It was too much for me to handle and as I felt her cumming deep in my mouth, I experienced the strongest orgasm of my life. I came so hard I thought I was going to bite down on Ashley's perfect cock, but I managed to keep her safe. As her orgasm died down, I continued to suck and lick her cock clean until she was completely flaccid.

I stood up with the biggest smile on my face, and kissed her hard on the mouth. She was breathless and went to the bed to sit down. I took the opportunity to pull my jeans on, put my shirt on and grab her thong from the floor. I walked over to the bed, gave her the agreed upon money and told her I was keeping the thong as a souvenir. I kissed her one last time, thanked her and left without looking back.

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AnonymousAnonymousalmost 8 years ago
Slutty sissy boy

I love crossdressing and using dildos on myself I can take alot in my ass my first dildo was my best friend sisters it was about 6 inches and a inch wide I used it for years till i moved to the city and got the nerve to buy some toys my first was a basic 8inch rubber dildo and a green jelly suction cup dildo and anal beads I used that for a while and went back and got a long rubber dildo then I got my first big dildo it was a realistic 12incher that's 3inch wide I love it it fills me up good but I'd love to get a shemale with a huge cock and dominant me like a dirty slut like make me suck her cock and slamming it balls deep and hold my nose so I choke on it and make me worship her feet and lube my asshole slamming her big cock deep in my ass I would love to feel a real cock and a set of big balls smacking my ass and the first time I'd want her to cum deep in my ass so I could push it out and eat it the next one I'd want to feel a big load of cum shooting down my throat

RebeccaCherieRebeccaCherieover 9 years ago
Yummy

Lucky Ashley :-)

Xxxxxx

AnonymousAnonymousover 9 years ago
Good short story

Many guys have same desire. Being able to go through with it anonymously NSA is great.

AnonymousAnonymousover 9 years ago

A waist is not a waste

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