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My Unexpected First Time With a Man

How a night of anal play, and crossdressing turned out to be my most intense sexual experience ever!
In the Arizona heat... It was Friday, the first day that I would be alone at home while my wife was on her trip. It was also the day that I timed a delivery of some clothing and accessories for a weekend of crossdessing and anal play. As I sat at work repeatedly checking the status of two shipments, one was a box of dildo's, lube and anal plugs, and the other was filled with lingerie, a wig, and a couple pairs of heels. "Out For Delivery" the status read... Out for delivery meant, I was going to be blown out of my mind in less than 24 hours.

As I pulled into my driveway I had a sigh of relief, my boxes were there waiting for me. I quickly grabbed the boxes off of the front porch and went inside to see what little presents were waiting for me. A box of lube, desensitizing lube to be exact, three dildos, and a butt plug. The reason for the three dildos was to help me stretch out going from smaller to bigger, all with suction bases for me to grind my ass into. Also there was the most important anal play accessory ever... the colt anal douche. I am a firm believer is a clean ass is a happy ass!

As I systematically set the play toys across the bathroom counter I looked in box number two, which was the dress up box. I pulled out all the stops here... ordering a ton of stuff to try on, and play in. As I pulled everything out of the box I decided that it was time for a shower and trim before I start playing.

After showering, and making myself squeaky clean (both inside, and out), and as smooth as latex I decided it was time to start getting dressed. First things first, the wig, and the make-up as Monika (my cd'ing alter ego), the women's clothes, and she was ready to get started. Teddy (eh), romper, (meh), halter top, and panties set (hmmm), I really liked the set out of all the lingerie I tried on. Out of all of it, the most inexpensive item was the absolute sexiest. Also sexy were the crotchless panties, but the set... that was had Monika, and trouble written all over it.

As I played dress up, had a little wine (Monika loves wine) and stretched out enough for the big dildo. I became bored. Pretending the suction mounted dildo was a big hunk just wasn't enough, I needed an actual person to play with. I started out on the chat rooms, then I thought, why not craigslist after hearing about the casual encounters section from a friend. I posted something about being a CD, and wanting to be watched and told what to do via skype. I planned on meeting a local guy on there, and having him stroke his cock to me fucking myself. To my amazement I received at least 10 guys local, with dick photo's attached in there email responses. Holy shit! This is awesome, and I got really, really hot looking at all of those fat cocks, with their delicious pink heads.

Kevin, an electrician or so he says, was the only guy to send a photo of himself, and his cock. He was even a few streets over which was crazy ironic, and very convenient. Kevin, was on the DL, in a relationship, and willing to go online for some video. I pointed him to a gay video chat room that I figured would be a fun place to start because we didn't have to share screen names, and get all personal. I could tell by our email exchange that he was a little weary since we were technically neighbors.

Into the chat room we went, I posted my live steam in one of the CD rooms, and I could see all the pop ups of guys in there stroking their cocks to me. I sat in front of my laptop fingering my ass, then playing with the dildos, doing a little dildo ass to mouth while at it. A couple of guys where really into it when all of a sudden, Kevin sends me an invite into a private chat room. We sat there and typed things back and forth, what I would like him to do, then what he wanted from me.

He was rock solid, and stroking his cock slowly. He was hot, thin, with abs, and not hairy. In fact his cock was clean shaven. During our play I watched him, and decided I wanted more. I asked him if he was alone, and he said yes. I told him we should really get together tonight so he could fuck my ass, and he was still wary.

As a few minutes went by you could tell he was starting to consider my proposition and then he asked, "What about you coming over and blowing me?"

I said, "Maybe, but why won't you fuck me? I've never topped a guy before, are you cleaned out?"

This is why any night you plan on ass play be it by yourself, or with others, its great to have the anal douche on hand. I told him I was totally clean, and let's start with BJ's and go from there. FINALLY! He agreed and invited me over. However it was only if I walked into his unlocked front door and start blowing him on the couch. I said YES!!!!

The adrenaline rush you get from meeting up with someone is fucking amazing. I was literally shaking, as I picked out an outfit to wear over to his house... It was fucking June in Arizona, and I was chattering, and shaking like a leaf. Then as I gained composure I saw Monika's favorite lingerie set, the halter and panties. On they went, I threw on some sexy club pants, a blouse and my heels. It was go time!

As I drove over I started thinking what am I doing. What if this is some guy fucking with me. Craigslist is filled with wacko's what if it's a bunch of guys waiting to mug me? I drove to the address and I started to chicken out. Not that I couldn't go through with blowing a guy (for the first time) but I didn't have the nerve to go to his door. I pulled in the driveway, backed out and left. I made a quick circle around his street as I thought about it, and as I passed by his house the second time I saw him on his front porch butt naked with his dick in his hand waving me over as he walked though his front door. I fucking trembled as I pulled up in my car, I felt hot inside, my stomach was twisted from excitement and adrenaline. This is fucking happening.

As I walked into his house he sat there on the couch as planned with his cock in his hand, and some porn on the TV. He asked me why didn't I come in like we planned and I said I was worried. He had me sit down next to him. I stripped down to my sexy set, and sat next to him.

"Damn you're hot" he said.

"Thank you baby," I replied.

He gabbed his cock and looked into my eyes, and down I went like a duck to water. I sucked the hell out of that thing. Stroking and sucking and licking his cock.

"Oh shit, where the fuck have you been hiding," he said as I worked even harder at giving him the perfect blowjob.

As I'm sucking away like a good lil' girl I started thinking if we were going to fuck, or if this was going to be a blow and go. Almost immediately as I started to think about that I felt his hand on the back of my panties starting to slide them over. His finger went into my ass, and he rubbed around the rim of my throbbing little hole.

"Is this what you want?" he asked.

"No, I want you to fuck me," I said.

He stood up, and said he would be right back. He came back with two amazing things, one, a condom, and two, some lube... at this point I knew we were going to have a great time. He put on the condom, and said he hated wearing them, but I told him it was a must. I mounted him in the reverse cowgirl stance while he sat on the couch riding his cock. It felt great, it was exciting, and very arousing. He had me stand up, and get down on the floor on all floors... he wanted to pound me like a little naughty bitch. He fucking hammered my ass, it hurt and he was going way to fast. I held my hand back to slow him down a bit as he grabbed me tightly and kissed on my upper back while he continued to fuck me.

We fucked for a few minutes as he told me how hot I was, and pulled on my cock from behind. When he felt my cock, and how hard it was he pulled out and told me how the condom sucked, and now it was his time to take care of me.

"But you didn't come yet!" I said.

He said it was ok, and started to go down on me. Getting a BJ from a guy for the first time was weird, but awesome, I motioned him to put his cock in my mouth as well so we would both have pleasure. As we 69'd he couldn't keep his fingers out of my ass, and finger banged me until I came. I came in his mouth as he swallowed, and just as I tasted his precum, he pulled out of my mouth, and flipped me over. I thought I was going to get fucked, and he said no, he didn't have another condom but he was going to do something better. I felt him spreading my ass, and as I looked back at him he told me to relax, he wasn't going to bareback me.

One thing better than getting a finger in your ass is a cock, but better than that is when a guy eats your ass like its a piece of pussy. Kevin was eating my ass, and it was the best fucking experience I have ever felt. He would eat it for a little, then finger me. He didn't touch my cock, and after a few minutes I came again.

"Oh my God that was amazing." I told him.

"Anything for you baby."

I came again, and it didn't seem like he wanted any return favors, and it was getting late.

"I'm sorry I couldn't cum" he said to me, "I swear I'm clean."

I told him I trusted him, but couldn't take any chances. We sat there and talked for a bit, and I put on my clothes to leave. He helped me with my things and told me how we should do this again, and I agreed. As I stood up to leave he stood to give me a hug while still naked. He kissed me on my cheek and neck, and said, 'see you next time'.

"Wait, I promised to blow you," I said.

He was just to hot to leave standing there alone. As I got on my knees to blow him he was even harder than ever. I sucked his dick and he moaned. He was loving it, and at one perfect moment I looked up at him with his cock in my hand and said, "You want to fuck my ass don't you?"

"Fuck Yeah," he said.

I told him, "I have a proposition... you can fuck me without a condom if we do two things..."

"Anything," he said.

One was we have to do this in a bed not the floor, and two I wanted to kiss. I don't think I could have ran back to his bedroom as fast as he pulled me. I knew at that point it was not only on, but was going to be special.

He took me into the bedroom to his messy bed, and threw me on it. I felt the pillow embrace the back of my head as he lay on top kissing me deeply with his tongue, and dry fucked my leg. He moaned again, saying how hot I was again, and how he wanted to fuck me all night. He undid my blouse, and kissed my neck and chest, then undid my pants and rubbed my dick. I moved his hand away and told him he can't touch me until he cums. Immediately he tore off my clothes, and flipped me on to my stomach. I could feel him eat me again, it was even better this time because it seemed "special". He then backed away and turned me to my side and started to penetrate me in the spoon position. I could feel it, all of it. His head, the contour of his cock, everything was much more sensitive without that damned condom. He said he wanted to spoon so he could kiss me while we fucked.

We made out, he fucked, my cock sat there bouncing but not being touched. He then got on top of me in a sort of missionary position so we could kiss easier, and I knew he was close. I could feel him thrust harder, and faster. His breathing changed, he was ready to explode. He continued to pump his cock deep into my ass until I felt his load burst inside of me. As he came, he moaned and bit the side of my neck playfully. He then kissed me for a while while it was still in, and eventually climbed on top to suck me dry. By the end of the event, the ecstasy I felt was unprecedented. It was unreal. I still masturbate to that night. My one and only night of sex as Monika. I want it again!

Monika, you little stinker... you and that damned halter set.

Oh how I wish I could re-live that night. Kevin, where are you!

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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