I had been spending a lot of time on the road working at trade shows and meeting with customers. Living out of a suitcase, I had very little time to myself. Not uncommon for a guy in my line of work, but it certainly put a huge strain on my family and relationships. The difficulty is not just the time, but also how we handled the stressful day-to-day issues. When I am not on the road, I’m able to take care of most of the things on the honey-do list. When I’m on the road, I hear about it, which makes things even more stressful since I am not there to handle it.
Dealing with the stress when on the road, can take a number of forms… Hitting the local bars and clubs, working out in the fitness center, sightseeing… damn near anything within reason, but nothing compares to that night I spent in the hotel on the last night of a two-week trip.
I usually always travel with a few “extras”. Usually, clothes that can be hidden with my man clothes… panties, pantyhose or nylons, a nightgown and maybe bury a dress at the bottom of my suitcase. That last night I decided to do a little shopping while I was in town since it was Wednesday and there wasn’t much going on… the weather was worsening and the snow was keeping everyone indoors. Before it had gotten too bad, I stopped at a local adult store near the airport.
While I was paroozing the aisles of videos and other novelties, I came across the toy section… “vibrator central”. I wasn’t planning on purchasing anything except maybe some supplements to help me into the mood, but one item caught my eye. I long realistic 10-inch dildo. Not sure why I was drawn to it, but it seemed to be calling me, so out came the wallet and into the black bag, it went.
I got back to the hotel just in time as the winds picked up and snowfall turned into a blizzard. As the weather took a downward turn, I went up to the room and checked my upcoming flight. I grabbed my laptop to learn my flight was canceled and I was stranded. I called the airlines and booked another flight home, but the next available flight wasn’t available for two more days. I extended my hotel stay and called the wife to let her know. While I had been stranded before because of the weather, this was the first time I was stranded in Europe. Being unfamiliar with the city also didn’t help… so I decided to try and make the best of it and it turned out to be one of the best weeks of my life.
I started with a pair of black crotchless pantyhose then pulled up a pair of black lace panties. Being gone for the week I had to pack wisely but enough to make it through the week. I was able to squeeze in a lacey black bra, a red cotton floor-length maxi dress and a nice pair of low heels. Putting on each item was getting me more and more turned on.
I grabbed my laptop and turned on the webcam taking several pictures and admiring myself. Sure I didn’t have makeup or a wig, but below the neck, I looked fantastic. I walked around the hotel room for a little bit, getting used to walking in the shoes again and then sat in the chair for a little while watching TV. Eventually, I felt so at ease, I dozed off.
I woke up about two hours later and initially forgot what was going on. That is until I walked into the bathroom and realized I was still dressed. I came back out from the bathroom and remembered the black bag still sitting on the bed. I removed the contents and ripped open the package.
It was absolutely beautiful… intimidating but beautiful.
I had never used one before, so I wasn’t quite sure what I was doing. I started by stroking it and as I did, without touching myself I started to get hard. I started to rub it up and down my body. First across my face and neck then moving it further down my chest to my legs and thighs. The feeling was getting intense. Then I started to go to the next level.
I brought the cock back up to my face and began licking the tip. Gently over one side, just as I like, then I wrapped my mouth around it, keeping my tongue firmly against the underside and began stroking with my fingers. Then I began to push it into my mouth. The thrill was getting me so hard I thought I would cum all over myself.
Restraining myself, I continued to orally pleasure my new “friend”… so much so I found myself drooling all over it. I moved back over to the bed, took off the dress and panties and laid in bed continuing to perfect my blowjob technique. I moved my laptop over to the bed and continued to record myself, then decided it was time to go all the way.
I pulled the lube from my suitcase and generously covered my ass and “my new best friend”. I moved to my side and spread my legs so I could reach my virgin hole. I slowly poked at my opening, which felt remarkable. Refusing to touch myself, I continued to play with my backside. Then, when I thought I was ready, I pushed the cock inside of me, slowly at first and as deep as I could get it. The initial pain was almost immediately replaced with joy and amazement as I took almost all 10 inches. I lost my grip and in the process tightened up and squeezed it out almost immediately, the feeling was enormous.
I switched positions moving to the floor and sitting on my knees I re-lubed and re-plugged my opening. The feeling was getting more and more intense, but I was having to hold it into position as I moved up and down. This became awkward and uncomfortable so I grabbed the suction cup attachment and went into the bathroom. I placed it on the floor making sure I had a good seal and tried again.
This time I had the best sex I had had in a long time – only I was on the receiving end. I bounced up and down on this shaft enjoying every inch. I continued this until I came all over myself. I remained plugged as I gathered all of my love juices and without hesitating, I rubbed it all over my mouth and licked my lips taking it in and swallowing what I had left. I got back up and cleaned up the floor. Cleaned off my face and went back to the bed where I eventually fell asleep.
I popped out of bed and went to find my “friend” once again. I re-lubed my ass and wedged the cock in between the mattresses. I got on all fours and backed up – just far enough to feel the tip hitting my opening. I was still a little sore, but ready for more, so I pushed back further penetrating my ass and I could feel the shiver throughout my body as I took every inch once again. I continued to take the cock doggie style until I was once again ready to cum.
I moved back to the bed propping my ass in the air and reaching back to continue fucking myself. With my other hand, I began stroking myself until I exploded all over my chest – shooting far enough to reach my mouth. I welcomed the load so much that I took the cock and rubbed my chest with it – coating it with the rest of my cum, then licked it off until it was completely clean.
The next morning I woke, still dressed and feeling like a used whore. My ass still sore and wet from the fantastic night of sex. And my face still covered in cum. I took a long hot shower and was thinking about what to do for the next two days. I went downstairs to the restaurant and had a cup of coffee and kept thinking about what had just happened. I was still very excited about it and wanted more. The question was… what more can I do?
After breakfast, I went back up to the room and search around for some fun places to hang out at. I had never been out dressed and wasn’t sure I could even go through with it, but I was willing to see if there was someplace I could go dressed where I would not be easily noticed. Unfortunately, with half the city shut down because of the snow, there wasn’t a lot of places to choose from.
I also had to consider my wardrobe. I didn’t have much and I didn’t want to be noticed as a “Lewinsky” for having cum covered clothes. I decided to walk the four blocks to the local shopping center. Most of the shops were closed, but a couple were open and I walked around and picked out a few things. The saleswoman approached me and I had to think fast. After telling her I was looking for a few things for my wife, she gave me a sarcastic smile and left me alone. When I was ready to pay, she continued to give me a sarcastic look which started to piss me off. It was obvious she knew what I was really doing, but she didn’t have to display it for me.
As I started to walk out of the store, she walked me to the door.
“Let me walk you out, I think I am going to close up now anyway.” She said.
“Okay, thanks again,” I said without even looking at her.
As we reached the door, she started to open the door and said, “If you ever need any help with make-up or shoes, let me know.”
I stopped in the doorway and hesitated as I looked back at her. As I did she was looking at me.
“I didn’t mean to embarrass you, but to be honest, I didn’t think you were really here for gifts for your wife.” She said, “At least not in this weather.”
I wasn’t sure why I stood still, but I seemed as frozen as the trees outside. She then extended her hand and pulled my dress shirt towards the edge of my shoulder exposing the bra strap.
“You might also want to try to remember not to wear a white shirt with a black bra… if you are trying to hide it.” She said.
As humiliated as I felt, she was no longer looking at me sarcastically and I started to think about the possibility of taking her up on her offer.
“How much would you charge me?” I asked.
“For what?” She replied.
“For the help,” I said.
“Come back in and we can talk about it.” She replied as she walked me back in.
She escorted me to the back of the store where she had a small salon and make-up vanity mirror. She had me sit down and went to work. I didn’t say much and while she was attempting to teach me, I don’t think I learned much as I was more focused on looking at myself in the mirror. The transformation was remarkable. When she was done, I couldn’t believe the difference.
“Okay, so let’s go to the changing room.” She said.
“What?” I asked.
“Don’t worry.” She said, “I closed the shop hours ago.”
So we walked out to the dark store and I walked into one of the changing rooms. A few minutes later, she knocked on the door to hand me several new outfits. I didn’t realize she was waiting outside the dressing room door and I was still wondering if I should even go through with this.
The next thing I knew the door opened and she walked right in.
“What’s wrong?” she asked.
“I’m not sure I can do this,” I said.
“Look, I am guessing you have never been out before.” She said, “Don’t worry about it. When I am done no one will ever notice… besides, you already have your make-up and hair done.”
She was so convincing, I immediately started to get undressed. She stepped out and came back with some very sexy lingerie. I started to get dressed and as I reached for the dress, she walked back in and helped me line everything up. Adjusting the straps to the bra and the nylons she picked out for me. After putting on the dress, she came back with a beautiful pair of black heels. Not too high and very easy to walk in. She then handed me a pair of boots I fell in love with.
“These will probably be better for you when you go back home.” She said.
She walked me to the full-length mirror and I was amazed at the result. I didn’t know where to start. Everything looked believable. As I stood there admiring my “new” self, she came back with a small suitcase. In it were the clothes I came in with and a few new things she picked out. Make-up, lingerie, a couple of skirts and the pumps.
“What do I owe you?” I asked.
“You already paid me, remember.” She said.
“No, I can’t let you do this.” I said, “There’s at least a thousand dollars worth of stuff here. I only paid you seventy-five dollars for the dress.”
“And that is all I am going to make this week anyway. Don’t worry about it, this was more fun.” She said.
After we were done, we hugged and I promised her I would be back the next time I was in town. She promised to keep our little secret and I started back to the hotel. On the way back I walked passed the adult video store and noticed the place was not only open but busy. Strange how it was late afternoon… I never saw a place like that start to fill up until well after dark. I thought about going in, but I was still not sure, so I put my head down and continued back to the hotel.
I quickly moved through the lobby and hoped to hit an empty elevator. No such luck. A young gentleman about my age rushed on behind me heading for the floor above mine. As we stood side by side, I noticed he was looking me over.
“Have any big plans tonight?” he said.
“Uh-huh,” I said in a high pitched voice.
“Awesome, you look really nice.” He said.
As the elevator doors opened, I rubbed his arm thanking him and quickly stepped off the elevator and headed for my room. Back in the room, I quickly grabbed my laptop and took a ton of pictures with my new look. Close-up headshots and full-length pictures, so I could try and duplicate what she had done.
As I started to come down from the emotional high, I sat on the bed wondering what my next move was going to be. I opened the curtains and looked out onto the snowy landscape. Off in the distance, I could see the adult store – still busy, but as night fell the place began to calm down. With each car that left the parking lot, my excitement grew until I almost exploded. So I decided to take another chance.
I grabbed my ID, the hotel key and the cash I had in my wallet and took the back stairs to exit the hotel and walked over to the adult store. As I started away from the parking lot, I heard a familiar voice in the distance.
“Have a great evening.” The young man from the elevator said.
I turned around and saw him leaning up against his car. I stopped and for some reason, decided to walk up and find out why he was standing in the snow.
“Why are you standing out in the cold?” I asked.
“Just waiting for the snow to stop before I hit the road again.” He said.
He was driving through town when the storm hit and when the roads closed he was stranded.
“Why don’t you go inside?” I asked.
“I’m not staying here.” He said, “I was just trying to get warm and maybe grab something to eat.”
“So why were you on the elevator?” I asked.
“I saw you.” He said laughing.
“You’re sweet,” I replied.
“So what are you doing out here?” he asked.
“I just needed some air,” I replied.
“Did you have to cancel your big plans?” he asked.
I didn’t know what to say. I didn’t want to come out and tell him where I was going and I didn’t want to keep talking to him because I didn’t want him to figure out I was not what I appeared.
“Bet it sucks not being able to go to a costume party when you spent so much time getting ready.” He said, “I mean you look great, I would have loved to have you as my date.”
What? How did he figure it out? Now I am not sure what to do. I was planning to go and shop or maybe catch a movie, but now I am thinking about this guy who was nice enough to recognize me and at the same time not judge me.
“Do you want to go with me to see a movie?” I suddenly asked.
“Sure.” He replied, “What did you want to go see?”
“I thought maybe just head across the street and see whatever is showing,” I replied pointing at the adult store.
“Hell yeah, let’s go.” He said and quickly moved towards me.
I took him by the hand and we walked to the store and after being shown to the theatre, we sat down and he had his arm around me as I had mine on his thigh. As the movie began, I was still a bit nervous. Every time he moved, I would jump a bit, but he was so nice and remained calm and it was very soothing to me as he rubbed my shoulder. The more he did the more I rubbed his thigh. The more action in the movie, the more I moved my hand up his thigh.
I looked at him several times noticing he was looking at me. When I looked down I noticed he was starting to show a little more of himself and if not for my coat in my lap, I would be showing more too.
His hand began to move from my shoulder down my back and I was getting turned on. While my left hand was on his thigh, I turned and used my right hand to slide up his other thigh and began rubbing his crotch. As I did our eyes locked and he kissed me. So passionately, that I couldn’t hold back any longer. I unzipped his pants and knelt down in front of him, pulled out his cock and went to town.
I slide my tongue over the top of his shaft, down one side and up the other, making him nice and wet. As I did he put one hand on each of my shoulders… never making a sound.
I began to swallow his cock. Taking it as far into my mouth as I could, pushing my tongue up against it applying just enough suction to get him to squirm. I then bounced my head up and down never stopping. His fingers dug into my shoulders every time his cock went further into my mouth.
I could hear him gently whisper, “Oh yeah, that feels good… Oh yeah… Oh yeah…” then his whispers became louder and louder as he was ready to explode, “Yeah… YEAH… YEAAAAAAAHHHH.”
With one more oral ride down his shaft, he shot his load into my mouth and down my throat. I pulled back leaving a trail of his sticky juices from my lips to the tip of his shaft. I then moved back in to make sure I cleaned him up swallowing the gift he was so graciously offering.
Afterward, I cleaned up my face and tried to make sure my makeup was okay and tried to help him zip back up. The movie had just ended and we quickly left the theatre. As we walked back I held his arm as he smoked a cigarette. We talked for a short time until we got back to his car.
“Do you have a place to stay tonight?” I asked.
“You’re looking at it.” He said pointing to the backseat of his car.
“It’s going to be cold tonight, come on you can stay in my room,” I said.
“I can’t ask you to do that,” he said.
“You didn’t ask, I am offering, come on,” I said as I took his hand.
We walked back inside and headed up to my room. Once there, he took a shower while I began to pack things away for my flight in the morning. As I was bent over with my back to the bathroom, I heard the door open and before I could turn around his hands were on my hips and he was pressing his naked cock up against my ass.
“I thought you were tired,” I said.
“I thought you wanted to have fun tonight.” He said.
I stood up and turned around and kissed him as he continued to clutch my ass. We moved to the bed and he continued to caress my body… I was powerless to move – enjoying the sensual touch of a man. I wasn’t sure if he knew the “real” me, but that was not an issue as he unzipped my dress and found my “gift”. I just laid there waiting for his next move.
“I’m sorry,” I said, “If you want to go… it’s okay.”
He never said a word, he sat up and grabbed my legs and flipped me over onto my stomach. There he spanked my ass repeatedly until it was nice and red. He then pulled my thong and moved it out of the way, and spotted the lube on the nightstand. I refused to move as I waited for another wonderful gift from a new “friend”.
I could feel his cold lubed fingers penetrating my virgin hole, as he began to spread my ass with his other hand, biting at my cheeks.
“I want to fuck you.” He said.
“I am ready for you baby,” I said.
He then stood up and I turned to see his rock hard cock standing at attention. I turned back around, closed my eyes and clutched the other side of the bed and waited for him to give me the gift of a lifetime.
He slowly poked me wit the tip of his shaft which felt so good. After repeatedly teasing my hole, he pushed in slowly.
“UH… UUUUUUHHHHHMMMMMM.” I uttered, “Yeah baby, just like that.”
He continued to push his cock inside me. As he did I could feel the warmth of his rod which sent shivers down my spine. After he was all the way in he began to pull back out just as slowly as he went in. The sensation was becoming more and more intense.
He pulled out and my hole clamped up and I almost fell over. He held me up and slowly drove back into me, speeding up with each thrust.
“OH YEAH… OH YEAH… YEAH BABY…” I shouted.
I continued to look through the mirror as he continued to plow into me, grunting with every penetration.
“UH… UH… UH…” I grunted, “COME ON… FUCK ME… OH YEAH… FUCK ME…”
He started to tire, so we switched places as I laid him on the edge of the bed. I spread his legs and sat on his rod enjoying my new seat.
“OHHHHHH… YEAH BABY…” He shouted as he tried to lean forward to watch.
I slowly slid down on his cock and the feeling was even more exhilarating. I got so into it I began to bounce up and down uncontrollably.
“OH YEAH… YEAH… YEAH… YEAH…” I screamed.
“I’m gonna cum… I’m gonna cum…” he struggles to say.
“COME ON BABY… CUM IN MY ASS…” I commanded as I continued to take his thick cock in my ass.
He was insistent and pushed me off him and I dropped to my knees as he stood up and exploded all over my face. He wiped his cock on my face as he squeezed out every drop. I took my fingers and wiped the cum from my eyes and neck and covered my lips and tongue. I then took his cock in my mouth to make sure I got every drop.
After we were done, I went to the bathroom to clean up and I wasn’t in there long when I heard the door open and immediately close. I came out to find my friend was now gone.
I checked my luggage, just in case, to make sure I wasn’t robbed and I looked out the window and noticed his car leaving the parking lot. I was a little disappointed until I noticed the note he left on the desk.
It simply said… “Thanks for a great time.”
The next morning, I finished packing and headed to the airport for my rescheduled flight. The entire flight home, I sat and remembered the wonderful moments of the last 24 hours. I returned home where my wife was waiting to pick me up. She tried to help me with my luggage and I was very careful to make sure she didn’t touch the new suitcase.
“Did you have a good trip?” my wife asked.
“Best trip I have ever had,” I replied
“Meet anyone new?” she asked.
I hesitated for a quick moment and then smiled and said as I looked back at my luggage, “Oh yeah.”