Loading...My name is Steve. I am a 27 year old salesman who travels around the north east US selling garden tools and supplies to department stores. This means I am frequently in hotels for a few nights a week. I tend to prefer the Courtyard Marriott style hotel – simpler, cheaper, and comfortable.
I am 5’7″, and about 180 lbs. I am in good condition as I work out on the weight machines at the hotels I am at, and ride my road bicycle for 50-100 miles on the weekends. I am single, but have a steady girlfriend who I just may ask to marry me some day soon!
What I am about to describe to you is a true story about something that happened at a hotel about a year ago. It changed my life forever, I think for the better… But if asked the day before it happened if I could see myself in the situation I am about to describe, I would have said no way!
So I woke up in the hotel one morning and got up to fix a cup of the in-room coffee. I always sleep in the nude, both at home and on travel, and last night was no different. As the coffee was brewing, I looked out the peep hole to see if the coast was clear for me to reach out and get the USA Today that is always at the door in the morning. All clear, so I opened the door a crack and listened. Nothing. Good. I opened the door a little more and saw that the paper was just on the other side of the door being pushed by it as I opened it. That made it necessary for me to lean out a little farther than usual to reach it, and as I did my foot slid out from under me and I fell out into the hallway! I watched in what seemed like slow motion as the door closed and latched, leaving me laying on my side naked in the hallway!
I quickly looked up and down the hall – empty…! I grabbed the newspaper and sort of wrapped it around me to cover myself. Great! Now what? I can’t go to the front desk like this! What will I do? I decided that I would knock on the door next to mine, explain what had happened if they open the door, and ask if they could either loan me some clothes or allow me to stay in their room with a towel while I had a spare key brought up for me. So I got up my nerve and knocked…
I saw the light dim in the peephole, so I knew someone was there and was looking out. For what seemed like forever, nothing happened. Then I heard whispering and a little giggling and the door cracked open with the latch holding it from opening all the way.
I heard a woman’s voice say “can I help you?”
Another woman was behind her giggling quietly. I quickly explained what had happened and what I wanted. The door closed and I heard some excited whispering, and then the door opened without the latch on it and the first woman said to come in.
It was then that I realized the two were quite attractive, late 20’s to early 30’s I guessed. One was wearing a long t-shirt that she had evidently slept in, and the other cotton panties and a half shirt. I could see the first woman’s partly erect nipples through her t-shirt and hoped that I wouldn’t get a hard on given my situation. They introduced themselves as Kim and Terri and reached to shake my hand, which I instinctively returned. Of course as I did the paper fell away and there I was naked in front of them. Both of their hands went up to the instinctive OMG position over their mouths, and Terri got a towel and handed it to me. I wrapped it around my waist, and felt a slight tingle as my cock began to realize the situation I was in.
“Do you shave your legs?!” asked Terri as she watched me put the towel on.
I explained that I was a road cyclist and shaved them for that reason. More giggling…
Kim was a very pretty blonde, with a short bob haircut and stunning blue eyes, about 130 lbs, 5’6″, and a very hot body, even in the t shirt she was wearing. She is the one in her late 20’s. Terri was a tall woman with big bones, about 5’8″ and 160 lbs. Though big, she was not fat and appeared very fit. Her body was firm and she looked good in her panties and half shirt.
I asked them if I could use their phone to call for a spare key, since obviously their women’s clothes wouldn’t do.
Terri told me their phone was not working and they didn’t bother calling about it since they got in late, and that neither one of them owned a cell phone. She then said that she thought some of their jeans would likely fit me, and I could just use them to go quickly down to get a key.
Kim said I could use her t shirt. Things were looking promising! Terri said to wait there, and they would bring the clothes out to me.
They both grabbed some things and went into to bathroom area. I heard some excited whispering and giggling, and they came out both wearing jeans and a shirt.
Kim handed me a little white lace pair of panties and said “put these on, you aren’t wearing my jeans with no underwear.”
I looked at her and said “no way, I’m not wearing lace panties!”
She said “ok then, there is the door!”
I was stuck… I looked at the panties – they were very lacy and sexy and had a little bow made of tiny pearls on the front.
Kim said “go ahead, I just took them off so they may be a little dirty, but they will fit you!”
Realizing I had no choice, I took them from her and held them up.
I had never had panties on before, but my girlfriend always wore sexy ones and used them to masturbate me once when we were having sex. She took them off and stroked me with them until I came. I must admit it felt good, and if she had tried to put them on me I probably would have let her. I sat on the bed and stepped into them, stood up, and slowly pulled them up. Oh my, they actually felt really good! They were tight around my balls, and pressed on my ass in a very sensual way.
Kim and Terri looked me over and said they thought I actually looked kind of hot in panties.
I felt my cock stir, and asked if I could please have the jeans because I didn’t like standing there in panties.
Terri said “you say you don’t like it, but I think you do… It looks like you are starting to get a little excited.”
“No, I’m not. I don’t like it.” I said.
She said “your mouth says one thing, but your dick is saying something else!”
They both laughed a little.
“Tell you what” Terri said. “Let’s do a little experiment. We will put lingerie on you, and if you get hard then we will know that you like it and are a sissy panty guy, if you don’t, then you get the clothes and can get your key.”
When I protested, I was told where the door was again… I thought what the hell, let’s get this over with.
“Ok” I said, “but I only wear it for five minutes, then we are done”.
“Deal” Kim said, and they hurried off giggling to their suitcases near the bathroom.
When they returned, they told me to sit on the bed and close my eyes. I felt them lift my right leg and put something on my foot, then kind of rolled and smoothed it up my leg. Stockings…! Then the other leg. They felt cool and nice as I moved my legs.
I was told to stand up and they slipped something over my head, again cool and nice.
Then they told me to open my eyes, and in addition to the panties, I had white stay up stockings with lace tops on along with a sheer white baby doll nightie! Kim had two other pairs of panties which she wadded up and put in the breast cups of the baby doll – the lace teased my nipples and it felt good!
Terri said “wait, I have just the thing to complete the look!”
She came back with a pair of silver high heels with 4″ heels and a strap that goes around your ankle. Since she was a big woman, she wore a size 12 1/2, and sure enough they fit me!
So there I was wearing white lace panties, lace top stockings, a see-through baby doll, and silver fuck me high heels while these two attractive women looked me up and down… How did I get into this??
All I could say was “the five minutes starts now!” I was determined not to get a hard on, and was thinking about fishing, cleaning the basement, cars, whatever guy stuff I could think of…
Terri told me to walk around the room, I did. And as I did, the panties massaged my cock and ass, the stockings and baby doll were cool on my skin, the heels made we walk like a sexy woman… I was having new and dangerous feelings.
They both sat on the bed watching, and I noticed they were holding hands. As I went by them, Terri slapped my ass and said “you look hot in lingerie and heels!” I felt my dick start to harden.
This can’t be happening, I thought. Fishing, cars, taking out the trash… But my cock seemed to have a life of its own. I looked at the clock on the night table – four more minutes if I can just maintain…
Suddenly Terri said “we need some ice! Steve, please go down the hall and get it, would you?”
“Absolutely not!” I said. “I’m not going out in the hall like this! What if someone sees me?”
Kim said “don’t worry about it! We will walk with you carrying this full bathrobe and if we see or hear anyone you can put it on. And besides, other than you, I think this entire wing is women from our fitness conference. If any of them happen to see you, I think they will like it!”
Well that explained why they were in such good shape, but I wasn’t really interested in any other women seeing me like this…
“You have three minutes left”, Kim said. “How much can possibly happen in three minutes?” Little did I know…
In a way, I was enjoying the situation, and did like the way it felt when I walked around in the heels and lingerie. So I agreed to do it! Kim handed me the ice bucket, and we headed out the door. The air was cool in the hall, and it felt good on my skin. And the way the high heels made me walk felt sexy… Try as I did to prevent it, I felt my cock getting hard. We were half way to the ice machine when Terri came out of the room and caught up with us. I wondered what she had been doing in the room… Getting the bathrobe I thought since she was carrying it.
As the three of us got to the ice machine, we walked into the little tucked back area where it was and I got ice in the bucket.
Then it happened… Terri said “look Kim, you were right! He has a hard on!”
“I knew it!” Kim said. Then she reached down and stroked me through the panties. Oh my! It felt wonderful!
Suddenly she reached under me and unsnapped a little snap in the crotch of the panties and pulled my almost fully hard dick out. The panties were crotchless! She started sucking me and stroking me up and down at the same time. There was no use – I had the biggest hard on I had ever had!
As my hips started to push forward and I felt that familiar tightening in my balls, Kim stopped stroking me and snapped the snap saying “not yet, our little panty boy”, my cock now contained and protruding out the top of the panty waistband.
“Take that ice back to the room now” Terri said. And we headed back down the hall.
I felt my ass swaying as I walked on the heels, and the cool air stimulated my body through the lingerie. I had lost the dare and we all knew it!
Then as soon as we came to the first door, it opened and two grinning women came out and whistled at me. Then two more, then more at every door we came to! Some looked and went back in their rooms giggling, others came out and started following us down the hall. I heard cell phone cameras snapping, and several of them slapped my ass or came up and rubbed my cock as it strained at the lace fabric. The reactions ranged from a quick look with a hand over a mouth, to downright aggressiveness!
One of them was also in lingerie and stepped in front of me and started rubbing herself over my front while she held my ass with both hands! I felt her hard nipples on my chest along with the lace from the panties stuffed in the cups of the nightie and couldn’t help but push my cock into her crotch. She ground into it while she grabbed my hand and put it on her panties over her clit. She was wet with her sex…!
She laughed, pointed out the pre-cum dripping from my cock, and wiped it up with her finger putting in my mouth after she did. It trailed from my lip to her finger as she pulled her hand away from me and I saw a woman taking a picture with her phone as it happened. She ended up following us to the room, while all the others slowly returned to theirs.
“What was that about??!” I asked Terri.
It turns out she does have a cell phone, and what she did in the room before she came out for ice was to activate the emergency txt warning network of all the fitness instructors. She told them all to come out and look as they saw us approaching through the peephole in their doors. She speculated that I enjoyed it as much as she did, which was true I thought to myself as I noticed my hard on was not going away!
Once back in the room, they introduced me to Audra, the woman in the lingerie from the hall who had joined us. She was a stunning red head with green eyes and a perfect body. About 5’6″, 125 lbs, and perfect tits with fully erect nipples showing through the red lace nighty she had on. And her matching thong panties looked amazing on her firm shapely ass. I noticed she was wearing black strappy 5″ heels that screamed fuck me!
When I managed to peel my eyes from Audra, I saw Terri and Kim locked in a deep kiss and removing each others clothes. All this didn’t help my hard on at all, and I just stood there slowly rubbing myself through the lace…
Once Kim and Terri were naked, Audra pushed them both back on the bed and started alternately licking their pussies. Kim and Terry were kissing and licking each others tits as she did it. After about five minutes of this, Audra came over to me and pushed me onto the bed between Kim and Terri in a sitting position. Kim rolled over me and went down on Terri with a vengeance, as Audra pushed a pillow under my ass for what reason I didn’t know or care at the moment.
I was completely into watching Kim lick Terri, and could tell that Terri was nearing orgasm. This has always been a fantasy of mine to watch two women together, but I hadn’t planned to do it dressed in lingerie and heels! I continued to rub my rock hard cock through the lace panties, and could feel the first hints of my own orgasm approaching…
All of a sudden I saw Audra reaching for the snap in my panties, and she was wearing a strap on dildo! She undid the snap and coated the dildo with lube. I realized what she was up to and started to protest, but she just pushed my legs up and said “you will like it, and i want to see your face as I take your virginity!” then she slowly began to push the head of the dildo into my ass…
It hurt bad and I said so, but she just dribbled more lube on my anus and said to relax and be loose. As Terri moaned in orgasm from Kim’s licking and fingering, I just gave up and let my legs fall open and relaxed.
I saw my lace top stockings over my shaven legs, and my silver strappy heels up in the air, as Audra slowly but steadily entered me to the hilt of the dildo. Then she turned on the vibrator in it… I went through the roof with pleasure!! She started to push in and out, and I felt filled inside and stimulated in a way I had never been before from the vibrating dildo massaging my prostate gland. I was dripping pre-cum like crazy and watched as
Terri and Kim switched places for Kim’s turn having an orgasm, which she did in minutes as she watched while Audra continued to work me with the strap on.
Terri then leaned back on the headboard spreading her legs, while Kim and Audra turned me over and pushed my head toward Terri’s pussy. “Lick!” Audra said.
As I started licking and lay down on my stomach, Audra pulled me up to my knees by my hips and pushed the strap on into me from behind. As she fucked me, Kim had her head under me and was sucking my cock.
As Terri watched us, she was very turned on and came in my mouth and all over my face with juice that tasted wonderful! Right after that happened, I exploded into Kim’s mouth with the longest and most intense orgasm I had ever had! Kim sucked on my cock head while she jacked me with her hand, milking every drop of cum from me… I almost passed out from the feeling and I felt my ass tighten and squeeze the strap on with each spurt of my cum. There was so much it was dribbling out the side of Kim’s mouth.
As I slowly stopped jerking and got my breath back, I fell onto my back next to Terri who was still having aftershocks as she moved a finger back and forth over her clit.
Audra pulled the dildo out of me and inserted it in Terri and started fucking. It was so hot to see, I didn’t notice what Kim was doing. She had gotten a second dildo with a ball on the end and a thick section in the middle, lubed it up and was pushing it into me. The ball end easily went in, and as the thick section entered me, it was pulled in and settled into place and she turned the vibrator on. The thick section inside me held the dildo in place and I started clenching my ass around it as the sensations of pleasure started up again.
Then Kim kissed me deeply, and I felt and tasted my huge load of cum fall into my mouth. As she pulled away there were strings of cum between our mouths, and she said “swallow it, you slut!”
I did, as I came hard for the second time that morning from the vibrator alone. No one even touched my cock that time!
Exhausted, we all slowly got up from the bed. I asked “can I take this stuff off now?”
Terri said “why don’t you just keep it since you obviously like it so much – the ass dildo too! And here is a spare key that one of the other ladies got for you in appreciation of the show in the hallway. You can just walk down to your room as you are – we all have seen you!”
And that’s exactly what I did, vibrator in and running and all!
Walking with the heels and vibrator was just too much, and I had yet another orgasm right there in the hallway as I approached my room. I then noticed two of the women who had seen me earlier watching me as my knees buckled and I came in my hand with what little cum I had left. They had just left their room two doors down from mine as I was approaching my room, and seeing them made me come all the much harder!
As I finished, I licked the cum from my hand and showed it to them in my mouth, then swallowed it. They both softly applauded, while one took a picture with her cell phone and told me to “have fun with my new toys!”
So that was the beginning of a new period in my life! That was a year ago, and today I am married to my then girlfriend, who I told all about what happened that night. As it turns out, she loves seeing me in lingerie and heels, and dresses me up almost every night!