This is a print version of story told to dress by pcarter from xHamster.com
Told to dress
I am a bisexual man, and I meet strangers for sex. I post advertisements on various message boards like Squirt and Adam4adam. I also post to Yahoo groups that are local to my area. However, the best place to find a no-strings attached meeting is on Craigslist. My advertisement usually is brief. White married bisexual submissive bottom seeks a dominate top. I am 58-year-old 5'-10' 210 lbs. short gray hair about 20 lbs. heavy but not fat. Looking forward to giving oral to completion nothing in return.
I get many emails asking for a meeting but only select a few too to meet. I received this one email from a man in San Diego, who was coming to my town for a few days on business. He wanted to meet. Since he would have a hotel room, I could meet him there. We exchanged email about what he wanted, which was a blow job and asked, "Do you swallow"
I replied, "Yes, I do."
In the next email he asked, "Do you know any she-males."
I responded, "No I did not, but if he was I might be able to find one. Most she-male's cost money but I will split the cost with you"
Next email he said, "Ok find a she-male but not a professional"
After his email, I started looking for a she-male started to look at Craigslist and found one about 30 miles away. I responded to her posting. Are you a professional she-male and if not would you like to meet two men?
She responded she was free to meet, and she had two holes each enjoying both filled. I asked if she was available on the night that my San Diego friend wanted to meet. She agreed to meet and offered to use her apartment, where I have all my clothes, and I can be ready for you two.
I sent emails back and forth coordinating the meeting answering questions, and the San Diego man was all excited about meeting a she-male. The she-male provided a photograph that showed that she had real boobs and a male member, a chick with something extra.
I had arranged everything, on the day before he was due to arrive, the San Diego man sends an email saying his business meeting changed, and he will arrive two days late. I said no problem I will reschedule. When I contacted the she-male, she apologized but was going to be out of town and cannot meet now.
I was now exchanging IM with the San Diego man, the IM when like this:
Reporting on my efforts to find a she-male on short notice I said, "Just talked to the she-male, and she will not be in town when you are here."
San Diego man in an upset and loud voice said (a few curse words), "then find another, she-male."
I taken aback from his outburst and demand, I said, "I have tried, there are none available. I did find one, but she wants $200 an hour."
San Diego man retorted, "I am not paying for sex, I want to meet a she-male or even a cross dresser."
I apologized for not being able to meet his needs, "I have looked on Squirt and on Craigslist, and I am telling you on short notice, I cannot find someone."
San Diego man continued with his appeal, "Look you promised me a she-male, you need to find one." He was very demanding and was upset about the change in plans.
Being perturbed with his demand and in frustration I said, "Look, what you want, me to do put on panty hose for you?"
San Diego man replied, "Yea, You do that, you dress up for me."
I was not inclined to play dress up and offer this excuse, "What, I have never done this before; I do not have anything to wear."
San Diego man insisted, "Well go out and buy something, make it sexy."
Resigned by his persistence, I agreed, "Well ok; I will do this but might only have panty hose and a bra on, I not going to buy a wig and a dress, ok."
He now sounded excited about meeting and urged me on by saying, "Yea that would be fine, I just want to feel nylon stockings rubbing on my legs."
We agreed, I would wear panty hose and anything else I could find or bought on short notice and meet him at his hotel room.
I went to Wal-Mart the next day. Walking around the woman's department looking at the panties and bras' sets from a distant, my heart was pounding. I was so embarrassed at the thought of buying woman clothes. I know that men shop for their wives all the time. So why would anyone notice to even care or me? So I walked down the panty Isle grabbed a red matching lace ruffle panty with matching bra. Next, it was to the stocking Isle and picking up several panty hoses making sure I got large size. I raced to the checkout line using the automatic check out a cashier would not see what I had purchased. I got out of the store, and my heart was still pounding. I had an adrenalin rush and was so excited about dressing up for this stranger.
In my emails and chats with San Diego man, we talked about me giving him oral, and then he was not interested in giving me oral. The meeting was planned; I would put on the panty hose, panties and bra. I would rub my nylon-clad legs against his legs he would get hard. I would perform fellatio for him, and we would both be happy.
San Diego arrived and attended his business meeting. I got a call from him around 6 PM:
San Diego man questioned, "Are you ready?"
Replying with excited voice, "Sure I am ready to meet you and can meet you at 7 PM."
San Diego man continued, "Do you have sissy things on now?"
I responded with sound of humiliation in my voice, "No, was going to get dressed at your motel room."
San Diego man shot back quickly, "No good. I want you to arrive with your things on."
I tried to offer my objection by saying, "No way don't want anyone to know."
San Diego man tries to convince me by stating, "Who is to know, put on your stockings, panties and bra, then you pants and shirt, no one will notice." Then states an order or else, he said, "If you do not arrived with your things on I will just cancel."
Not wanting to disappoint him I reluctantly said, "OK I will, I will do this. It should not take me long to get the things on."
San Diego man, now order me saying, "When you arrive, the door will be open, you knock and I will go into the bathroom, you enter and take of your shirt and pants. I only want to see you in panty hose, panties and bra."
Submissively I responded, "OK will be there at 7 PM."
I got naked and took the panty hose out of the package. The package said they were large but looked small. They were black and shear. Is there a front or back, no? OK, how do you do this, one leg at a time? I had to roll up the leg, slide my foot in to the tip, then pull and unroll the stocking to the knee. I did the same for the other leg and standing up pulled on each side so the panty hose pulling up and covered my butt and to the waist. I smoothing out any wrinkles in the stockings and looked at my stocking covered legs. I commented to myself, I had nice legs. I am not hairy man so my legs looking more female than male. On went the panties, then the bra. Wow the Bra was tight. I bought a large the strap and bra pressed into my skin restricting my ability to take a deep breath. I put on my pants, shirt and shoes.
I drove to the hotel thinking that everyone was watching me and knew I was dressed in woman under. I prayed not to have an accident or topped by the police. You could not tell I was wearing panty hose, panty and a bar but jus the same I was very self-conscious of sissy condition.
I arrived at San Diego man's motel a little be fore the scheduled time, I sat in my car until 7 PM. I found the room number and knocked on the door, I heard an answer, come in. I pushed on the door enter the motel room and closed the door behind me. I took off my shirt, pants and shoes as arranged to reveal my male body wearing black shear panty hose, red ruffle panties and a red underwire bra. I do not have big breast but the bra did giving the appearance that I had at least a A cup.
A man walks out of the bathroom with just a towel around him, he say hellooo and shook my hand. I said hi, lifted my arms, and twirled around so he could see all of me. He sat on the bed and asked me to stand in front of him. The panty hose was shear and black but you could see my semi erection bulging off to one side. He undid the towel exposing his genitals and he was flaccid. He turned me around so I was facing away from him and pulled me down to sit on his lap. I was in the classic lap dancing position and so wiggle my bottom on his legs and rocked back and forth on his male member. It was not long before I awaked his hardness between my legs. I continue to rub my bottom on his erection while he felt my breasts and slipped his hands into the bra from the top to play with me nipples. He got my nipples hard; I got his limp member hard.
He told me to stretch out on my knees. I did as ordered. I saw his erection for the first time and could see a cut phallic about six inches. Standing in front of me, he places his hands on each side of my head, pulls forward and down so directing me to give him oral. I open my mouth, accepts his hardness into my warm wet mouth and I hear him moan and tell me that feels good. He keeps his hands on my head moving his hips up into my mouth that restricted from moving by his hands. We do this for maybe five minutes when he stops and tells me to stand up. He slides my panties down to my ankles.
Standing up and he turns me around pushes me onto the bed so my knees are on the edge, my hands starched in front of me, I am in the doggy position. He rubs his cock along my crack and tries to rip the panty hose but no luck he reaches for a pen and pokes a hole in the panty hose at a location in line with my anus. I did not expect to receive anal intercourse tonight, was just looking to receive oral. As he rubs his erection on my panty hose, aroused and grabs my hips and dry humps me.
He f***es me on my elbows pull my hips up and slides the gland head in the hold of the panty hose and to my rose bud. I have only had anal a few times and I know I had to relax and let him do what he was going to do. I relax, the gland entered, I relaxed more and it slipped halfway inserted. I was tight and no lube so had to reach behind me and spread my cheeks. With the last pushed he was all the way in, smoothly moving in and out.
He leaded over grabbing my bra squeezing them, pinching my nipple at the same time. This caused me to tighten on his member inside me, which give him some pleasure. The speed picked up, the thrusts were deeper each time and then he let out a moan held my hips so I could not move and his climax was way up inside me. All this happen so fast that I did not realize San Diego man did not use a condom. I collapse on my side with San Diego man rolling with me his manhood still inside me. We lie there for a few minutes when his relaxed spent male organ slipped out of my now dripping wet anus.
He patted me on my butt said I was hot in panty hose. He started too dressed, mentioning that he had nothing to eat. He told me to stay dressed. I excused myself to go clean up and return, kept the stocking on, putting the panties back on and wearing the bar, then finished dressing. We drove to a restaurant with my sissy thing under my clothes. We had before dinner drink, during dinner drink and after dinner drink. Good his motel was not far way. After dinner, I was thinking I would now go home but he asked if I want to return to his motel room.
Well the story goes on, sex again. I spent the night and was there for him the next morning when he woke up with the usual woody. I left the motel early in the morning, went to my place, cleaned up and was an hour getting to work. I get a text message from the San Diego man, "I want to meet you again tonight."
I texted back, "Sure, what do you want me to wear?"
Story URL: http://xhamster.com/user/pcarter/posts/91122.html