Home Alone One Weekend

I was 34 years old when this took place. I was married, not happily married, but married. She knew about my past but mostly ignored it and I didn't go into much detail. It didn't turn her on or excite her or anything. The extend that she knew was a transgendered person named Ramona and that was about it. She never asked or wanted to know details.

When we moved in together I threw out my 'Anne' identity and thought I could move on. I was mistaken. We were married just under three years and the sex had gone from a frequent event to a rarity at best. I was wanting it, she was not. So I spent my evenings looking at porn, and after a few weeks I started looking at the personal ads, then the casual encounters. I wasn't looking to answer any of them, at first, just imagine being with that person.

It was a Friday night. She went to bed around 9pm complaining of yet another headache (this was after working and coming home right before me, where I cooked and cleaned the kitchen...and SHE had the headache) and I went from porn to casual encounters and looked. She was computer illiterate, so I knew she'd never look at my browser history, especially after I told her that there was no such thing. I saw an ad, it was in my area. A transvestite (Robyn) was traveling and wanted someone to visit for a quickie in the hotel room.

I replied to the ad assuming that there would be so many responses that mine would get buried. Nope. There was an almost instant reply. The shuttle bus was going from the airport to the hotel and she'd be checking into her hotel in about 30 minutes. The hotel wasn't far from me. My mind worked as my dick throbbed with anticipation. Could I really do this?

I told Robyn, that I would be there in about an hour. I chilled at home for a bit. It wouldn't take 20 minutes to get there. The wife was sound asleep thanks to her sleeping pills and I could drop a piano in the living room and she wouldn't know it. The wine she had with dinner also helped her sleep deep and heavy. But just in case I went through the kitchen to see if there was anything that I would want that we didn't have. Cookies. We were out of cookies. If she asked I went to the store to pick up some cookies because I wanted some.

It was after midnight when I got to the hotel. I had to be let in personally by the desk clerk who eyed me funny as I told him that I was there for a quick visit. I didn't tell him which room, he didn't ask. But I could almost feel him thinking that I was going to Robyn's room.

I got to the third floor and made it to Robyn's room number. The door wasn't closed all the way, slightly ajar with the inner lock being used to keep the door open. I softly knocked on the door and said "Robyn?"

I heard Robyn's voice "Rick?" she replied back.

"Yes."

"Come in" she said, "I wasn't sure if you'd be here."

I entered and didn't close the door all the way as I forgot to move the lock thing out of the way.

The room was dark, but we found each other, kissed instantly and she reached for my pants and hurriedly took them off. She was in a basic nightie. I reached under it and stroked her dick as she pulled my shirt over my head.

I broke our kiss as I dropped to my knees and took her thick and hard dick into my mouth. She moaned and said "I wasn't expecting this." I thought "This was the part I was looking forward to the most."

She pulled me off her and laid down, face down, on the bed and said "Fuck me."

I did as as she asked. She took the time to lube herself up before I got there. Her ass was tight, very tight, and with it having been as long as it had been since the last time I had sex, it really wasn't long at all before I came in her ass.

She cleaned me off and thanked me for my visit. We kissed again and she reminded me that this was just a quick fuck and go, no staying at all.

When I turned to leave I noticed the door wasn't completely closed. I got closer and was relieved to discover that there was no one spying on what we were doing.

I went straight home with the cookies I bought before seeing Robyn and acted completely innocent (after chewing a lot of mints and gum). The wife didn't even realize I had been gone, which is completely what I had expected.

The next month continued as any other month for us had. Her sleeping long hours, me alone in the living room after dinner. I stopped looking at the ads. I don't believe she suspected anything, I just didn't want to press my luck.

She announced some time after that she was going away for the weekend. A friend of hers was getting married and she wanted to be there for it. Since it was a four hour drive, one way, to get there, it was going to be a weekend trip. Since her friend and I didn't get along, I wasn't invited. I didn't argue it. After all, it gave me a great chance to play, and I was going to play.

That Friday finally came, we got home from our jobs, she changed clothes, grabbed her bags and she was gone not long after another of her friend's picked her up. I continued about my day as normal. Had dinner, watched a movie, that kind of stuff. The wife sent me texts every so often on her drive south.

The wife was a BBW, and I wasn't a large person, overweight but not large. This made it easier for me to put on her clothes. I regularly shaved my body in the shower, so I didn't have to worry about any grooming (the wife did enjoy this, she wondered about it early on, I just said something about it being hygienic to have a shaved chest, legs and manscaping). I also scoured the online ads, didn't find anything of interest at first, and later, when I did, it didn't pan out.

At 1 in the morning, I called it a loss and went to bed.

When I got up and showered I decided to take matters into my own hands and make my own ad. So, fresh from the shower I put on a short skirt, a blouse, and a wig that she had from halloween several years ago, and posed for some pics using the timer on my tablet. Then I put on regular clothes and went about my day as normal.

It was around 8 or so that night when I started to think about what I had done and was planning on doing. "What was I thinking?" I thought to myself, "She's going through something and I've already played around on her once and here I am, planning on playing around on her again in her clothes on our bed. This sounds messed up."

I was about to just put on a movie and push the entire idea of what I was planning out of my mind forever and delete those pics from before. Then I got another text from her (she had been sending me texts all day). One was of her friend and her new husband, the next was of her and her friends leaving the reception now that it was over and going to a bar to continue the party. And the pic of her and her friends all looking like horny sluts out looking to get laid. That kind of ticked me off. Not that she was out having fun. But how when she was at home all she wanted to do was come home, have dinner and go to sleep complaining of headaches. Even when our friends and family sent us invites of upcoming events, she didn't want to go because she wasn't in the mood and I couldn't go because that would be just wrong. So here I am, at home alone, have missed so many events hosted by friends and family that they've stopped inviting us, and here she is, suddenly, not having a headache, suddenly able to keep her eyes open past 8pm. This hurt. Worse is that she kept asking if I had cleaned up something here or fixed something there. She's having the time of her life and giving me chores to do in the process.

Now I remembered why I had considered doing what I as doing.

I went online and posted the ad and the pics. I was going to host. I wasn't going to do this in the master bedroom. But we were living in a two bedroom apartment and there was a bed in that room for guests (by guests, her family and friends). I looked through her clothes to see what she hadn't worn in a long time that I could use. I was getting email replies to my ad. I was filtering the replies. Finally a reply caught my attention. He was a bisexual 19 year old who was looking for his first time. We exchanged emails for a bit and he hadn't been with anyone, ever, and was looking to lose his virginity. Honestly I couldn't believe this. I saw his pic and virgin or not, I was willing to please him. So I sent him my address and told him that when he got to the apartment complex to email me and I'd send him the apartment number.

I lowered the lights in the living room and guest bedroom. I ran to the master bedroom and I stripped out of my clothes and got ready. I put on a thong that I hadn't seen in so long I forgot she even had it. None of the bras were going to work. She was a D cup and I wasn't going to even attempt that. Oh well. I put on a little black dress that looked shorter on me. Applied the wig, added some stockings and waited.

He emailed that he was here and I sent him the apartment number. I heard footsteps outside. I looked out the master bedroom window and I saw him and no one else. I do get paranoid sometimes. I ran to the door as he knocked. I answered the door and invited him in.

He was a bit shorter than I, not scrawny, but not muscular either. He did take pride in how he looked. We shook hands and he was very nervous.

"Would you like something to drink?" I offered.

"No." he said uneasily.

"Relax." I said, "No one is going to harm you or anything." I explained while pointing to the couch.

"I just...I just haven't done this before."

"That's alright." I replied sitting down next to him.

We talked for a bit. He calmed down and relaxed. I moved closer to him, he put his hand on my leg and I moved in to kiss him. We made out like school kids for a bit while feeling each other up and I began to undress him.

I looked at this hard dick and I put it into my mouth. I didn't give him the best blow job that I could. I didn't want him to finish too soon and leave. But I did make him moan with enjoyment.

I released his dick and I laid back on the couch and I moved his hand to my skirt. "You should always reciprocate." I said as I lifted up the skirt.

He got what I was wanting and he dropped to his knees. It may have been his first time, but he was a natural at what he was doing.

He stopped and put my feet in the air and moved the thong out of his way. I was surprised by his sudden boldness. He grabbed his dick and he went searching for my asshole. Most of the time people just want to go doggy style, it's easier. No, he wanted it on my back on my couch, and I wasn't going to argue.

I couldn't keep my mouth shut as he stretched me out. I looked him in the eyes as he slowly humped me and then picked up the pace, faster and faster. I couldn't keep my hand off myself, stroking my cock as his slid in and out of me.

I came as he pulled out of me. I came all over my wife's black dress and he came over my face.

He collapsed on the couch in the corner of it. I licked the cum up from around my lips and I said "I'm going to take a guess that you weren't actually a virgin."

"No." he answered, "I learned that by saying that people take more notice."

"What kind of people?" I asked, "Horny cum sluts like me?"

He blushed, "That's not what I was saying."

"Please say it, I want to be told that..."

"Seriously?"

"It's a turn on, it makes me feel...sexy."

"It allows me to stand out for slutty bitches like yourself who want a young man's cum dripping down your face."

I smiled.

"You really did like that."

"You could have called me that while you were plowing me and I would have come instantly."

He stood up and started looking for his clothes. "I think you might have a problem."

"What do you mean by that?"

"You're clearly married, probably wearing your wife's clothes and fucking young men and wanting to be insulted. You're messed up."

"You lied to me so I would fuck you. Don't think for a moment you get to stand on some form of high ground."

He was almost dressed at this point. I stood up and walked up to him. "You're an asshole."

He reached out and scooped the cum on my face with his fingers and forced them into my mouth. "Make sure you eat all this cum you whore."

I did as he asked, sucking his two fingers clean in the process.

He scooped up what was on my dress and fed it to me.

By the time we finished that I was hard again, and I suspected he was also. My suspension was confirmed when he spun me around and bent me over the coffee table, lifted up my skirt and fucked me yet again. Oh, this felt good. Fast and rough.

"Take it slut." he called out. "Enjoying it bitch."

"Yes." I called out in response.

He got faster and faster and without warning, he shot his load into me.

He paused for a bit before slowly pulling out of me. This time he didn't say anything. He pulled up his pants and left my apartment. At least he was kind enough to close the door as he left.

I went to the master bedroom and jerked off one last time as I felt the cum draining out of my ass.

I rested a bit before throwing the sheets into the washer and changing out of her clothes.

By the time she got home on Sunday, the bedding was out of the dryer and on the bed. Her wig was back where she kept it, the ad was deleted, so were the pics and all emails from that ad. Her stockings, black dress and thong were in the dumpster. The stained couch cushions were flipped over.

She didn't seem to notice anything had happened in her absence. I just told her that I hung out at home all weekend doing nothing.

We were together for about eight more months. Never in that time did she realize her dress, stockings and thong were missing. A quick check on her phone later that day while she was in the shower proved that she wasn't just drinking at the bar, but her friends had taken pics of her getting felt up and grope by various strangers.