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Ian's Adventures - Part Two

"Another fun trip planned"

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My name is Ian and this is the story of what happened to me on my latest business trip. Just to refresh your memory, I’m in my forties and have brown hair and blues eyes. I’m in excellent physical condition. I’ve been married for sixteen years, but have vanilla sex with my wife. I’m bi-curious and this is my story.

I was pretty excited for my upcoming business trip. I’ve been doing a lot of masturbating lately and have been thinking about buying a new anal toy. I really can’t play too much with these things at my house in fear that my wife might find all of my toys. I have a stash of them, but I try not to have too many things in my collection.

When I travel, I tend to treat myself with toys that I wouldn’t normally play with at home. I decided that I would buy a suctioned cup cock shaped dildo. I was really excited because it was much larger than anything I’ve ever played with before. It was very thick and very long.

Since I was going to be on my upcoming business trip and would be away from Monday through Thursday, I decided to go online and make the purchase. I told them to ship my package to the hotel that I'd be staying at. For days, I just dreamed of the feeling I'd feel when I fucked this toy up my ass. I was getting very aroused with the thoughts of the orgasm that I'd feel. My cock was leaking pre-cum, while I fantasized about this.

I had to take a moment and stroke my cock. I moved my fingers up and down my shaft. Cupping and holding my balls as my fingers danced along my shaft. I stroked myself slowly and then a little faster. The idea of me riding the dildo cowgirl well fuck it will have to be cowboy was making me so excited. I would slap my ass up and down over the dildo. The more I thought about it, the more I was jerking my cock so fast. My pre-come was leaking out of my cock. I swirled my finger to taste my fluids.

“Oh fuck, my cock is so fucking hard. Oh God! Oh fuck!”

I normally edge for hours, but this thought was way too exciting and I blew my load right into my hand. I licked my palm to taste my hot and salty cream. What an amazing fantasy that was. This was making me so excited to go on my business trip and fuck that dildo. I figured, since I’d be in town anyway, I would make an appointment with another escort that I’ve met on several occasions, when I’m in town. It would be very exciting to masturbate with my new toy and get together with my escort friend.

It was very important to have the toy shipped expedited shipping to the hotel. I would get my new toy on Monday when I arrived. My escort friend was available on Wednesday night. I figured that was good, because I could have a few solo nights with the new toy. It was a very large cock and very thick. I never had something so big up my asshole before.

Moving ahead several days, I finally arrived and I got to my hotel on Monday night and there was no package at the desk. I got an email from the company that it would arrive on Tuesday. Unfortunately the toy never arrived, but I got a new email saying the toy would be here on Wednesday.

Now I was really hoping it would come because I was meeting my escort friend tonight. Unfortunately, now I wouldn’t have time to get used to it. I wanted to be able to stretch my ass out and really be a pro by the time I met my friend. While at the office on Wednesday, my boss called to let me know he needed me to extend my trip until Friday. I had to call the hotel to extend my stay. While on the phone, the girl mentioned that a package had been shipped to me and to check with them when I got back to the hotel.

I was really excited that the package was delivered. I’ll tell you the way the woman said the package was there was really weird. She said it in a way that she knew what was inside. In the past, I’ve ordered things and they always ship in a plain box. I really wondered how she could possibly know what my delivery was. In a way, it was kind of exciting to think that maybe she did know.

I then texted my escort friend and told her to meet me at my hotel at 10:30 PM. She said, she was looking forward to seeing me. After a long day of meetings and a business dinner, I headed back to the hotel and stopped at the front desk to pick-up my package.

“Hi, I’m Ian and I was told there was a package here for me.”

“Hello, yes it did arrive. Let me get it for you.”

The woman looked at me with a sly smile and turned around to get the package off the back counter. She handed it to me still smiling. As I walked away, I noticed the box had been opened. I got in the elevator and was trying to figure out why the box needed to be opened.

I saw that the shipping label had my name cut off. So the front desk only saw my first name. They had to open the box to see the packaging slip with my full name, which was attached to the clear wrapped dildo. I really got quite a rush and I felt really kinky knowing the cute girl at the front desk knew what I had ordered.

I only had about an hour before my escort friend was coming over. I had to give myself a thorough enema. After that, I took a shower. I really didn’t have much time to play with my new toy. But, I did take it out of the package and was just amazed on how thick it really was. I couldn’t even imagine how this was going to feel up my ass. It was very exciting and I could feel my cock stirring.

It really looked like a real cock. It was spongy yet firm. It was beautifully crafted with a nice mushroom head. I washed it with warm water and soap. While I was just stroking it, my cock was semi hard. After I cleaned it, I kissed and licked it. Then I sucked on it and I was getting so aroused.

My phone then rang and my friend was in the lobby. I told her I would come downstairs to get her. She and I have played a number of times together, but we’ve never fucked. We just masturbate for each other.

She is petite about 5’1” and maybe one hundred pounds. She has small breasts and a really nice body. She is Korean and is twenty four years old. She’s half my age, but that’s what makes it very exciting.

I went down to the hotel lobby and went to get her.

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“Hey, how are you?”

“I’m great, nice to see you.”

We then got into the elevator. We exchanged a welcoming hug and then waited to get off the elevator. We then walked to my room. Once inside we started to talk.

“I got my new toy. I can’t wait to show you.”

“I can’t wait to see you ride it. It sounds really sexy.”

“Wow! That’s really big. I can’t believe how thick it is.”

“I know! I’ve been dreaming about this all week. I wanted to get some solo time in before seeing you, but the shipping got all fucked up.”

“Don’t worry. We can experiment with it together.”

We then sat on the edge of the bed catching up. She’s a really nice girl. She’s taking college classes. While we were talking, I held the toy. She was just giggling and listening to me talk.

“I’m married, but I’m bi-curious. I’ve never slept with a man before, but I’ve been with a shemale and we’ve enjoyed oral sex together. But, I’ve never had anal sex by way of a man. Although, I’d like to experience it someday. But, for now I just play with anal plugs and dildos.”

I could tell she was very curious and listened to me talk. She was watching me stroke, kiss, and suck on the dildo. We both started to undress. She was really cute. She had a really hot body. She had a smooth bald pussy, smallish perky breasts.

As I got undressed, my cock was past the semi-hard state. Earlier in the week, I had done some manscaping. I was smooth all around the base of my cock and balls. I had a pubic hair strip that I trimmed.

She was on the bed and she was on her elbows with her legs spread. I was sitting on the edge of the other bed. I was watching her as I played with the dildo cock. I was stroking and sucking it as she lightly ran her fingers over her pussy, which got glistening quickly.

“I’m going to have to warm up a bit. This cock is huge.”

We both giggled. I lubed my ass and started to finger myself, which was really hot to do. While I was doing this, she was watching me and was playing with her nipples and pussy. I was now fully hard as I worked two fingers up my asshole. Once I felt I was ready, I took the dildo and placed it onto a small table. I placed the table between the two beds. I covered the dildo in lube and I was stroking it. Then I faced her and hovered myself over the cock head and pressed it against my rosebud.

“Oh my, this is so fucking thick.”

I bumped against it a few times just to get my rosebud familiar with what I was going to be enjoying. I did this over and over again until I was able to press down on it. I felt the tip of the head push into my anus and then I felt a pop. The head of the dildo slipped in and it felt like heaven on earth.

I just let it sit like that for a little bit. All the while, my escort friend was watching and she was masturbating. She then took out her vibrator and started to run it against her bald pussy. At times, she would lick her vibrator and put it on her pussy and then put it back into herself. It was so fucking hot to watch her.

“Oh God, my vibrator feels so good. My pussy is so wet. Do you see how wet it is?”

“This toy feels so good up my asshole. Fuck! My ass is so tight.”

I then rose up a little and the toy slipped out of my ass. Then I went back down and did this several times. Each time going a little bit further down. I was in great rhythm riding this dildo. My cock was already seeping strings of pre-cum dangling from my tip. Up and down I rode this cock.

“Fuck this feels so fucking good. Shit!”

While I was fucking myself with the dildo, I would stroke my hard cock ever so slightly. My cock was rock hard and throbbing. My friend turned her vibrator on and started to work her clit, which looked so deliciously aroused. I loved watching her masturbate for me.

“Oh God, this feels so good. Oh fuck! My pussy is so wet. Do you here it squelching?”

She was twisting her nipples, while I was riding the cock up and down. It didn’t take very long for her to come. Her pussy was spasming as she squirmed on the bed. Her clit was dancing. I started to stroke my cock and really fucked the dong. I was really wishing it was real. I wanted her to see me fucking a real cock. I was so lost in seeing her pleasure herself and watching her come.

I could feel my own orgasm building. The dong was getting more and more buried in my asshole as I stroked my cock harder. My prostate was fully aroused. I felt my balls tighten and the first orgasmic wave overtook me. My come throttled through my shaft and shot out hitting the bed that she was on. My come landed between her legs. She was enjoying her post orgasmic bliss lightly stroking her pussy as she watched me come. I shot another blast of come.

“Fuck, I’m coming. Shit!”

I found it difficult to maintain the squat over the toy. I leaned forward slightly as my orgasm rolled to the second wave. Come was now streaming instead of shooting. I lurched up off the toy as my cock twitched. I stroked my cock harder and faster for the finale wave, which resulted in a final smaller shot of come. I then slowly stepped back and sat on the bed facing her. I was laughing as my cock twitched.

The dong was sitting proudly on the table glistening from all the lube. I leaned back onto my elbows and played with my cock.

“That was fucking amazing. I’ve never been so fucking turned on in my life.”

She giggled.

“It was really hot. I really enjoyed watching you ride that dong. You really looked like quite a pro. You’d never believe it was your first time playing with it.”

“I liked watching you play with that gorgeous pussy. Your pussy lips are so beautiful and you have amazing breasts. You’re so fit and have a tight little body.”

I tell you it was post orgasmic bliss. We hung out for a little while and then she took a shower and I paid her. After that, I went on a website that I enjoy and told a friend about my adventures and then jerked off, while I relived it. It was the best business trip I’ve had in a while.

*I wrote this for a very good friend of mine. I really hope he enjoys it.....xo


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Written by Mysteria27
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