First time Crossdressing

I am a bisexual man, meeting straight, bisexual or gay men for our sexual pleasures. I post messages on various message boards like Squirt and Adam4adam that allow members profiles and posting messages. I also post to local Yahoo groups in my area that allows one to post messages to a small geographical area or to a distant user group. However, the best place to find no-strings attached meeting is on Craigslist where you can post an advertisement for a geographic area in a personal group erotic meeting male for male. My posts are usually brief, 'White married bisexual submissive bottom seeks a dominating top. I am 58-year-old 5'-10' 210 pounds short gray hair about twenty pounds heavy but not fat. I am seeking to give oral to completion for nothing in return.'

In my younger day, I was constantly searching to meet strangers for adult fun, to give them oral without the man having to give anything back in return. I had regularly posted advertisement to personal encounters of Craigslist, resulting in receiving several e-mails a week from men wanting to meet. I answered every e-mail asked them when they could they meet, where could we meet and when we met, what did they want to do. When they responded, with the necessary information, I reviewed their information then decided if I were willing to meet. E-mails were from local men or from men traveling and want to play when they were away from home.

I received one e-mail from a stranger in San Diego; his name was Ray. Ray was coming to my town for a few days on business, mentioning my advertisement posted on Craigslist. He wanted to meet me, so I could give him a blowjob. Ray and I exchanged a few e-mails and I agreed to meet him because he could host at his hotel room. In his e-mails, Ray asked a strange question, "Do you know any transvestites?" Ray mentioned he had a fantasy about meeting a chick with a dick. In my e-mail back to Ray, I told him that I had a fantasy about a Tranny topping me. I told Ray I would look around for what we both had erotic fantasies. I provided Ray my phone number should we need to speak about our threesome. The next-day Ray, my cell-phone rings and it was Ray.

First question after hello, Ray said, "Do you swallow or spit?"
I responded boastfully, "I like letting a man shoot off in my mouth and having him tell me to swallow his load."

Ray continued, "Good; I am straight man, and not interested in sucking any cock. So you'll do fine." Ray continued his questions; he asked, "Did you find a chick with a dick yet?"
I responded, "No, not yet; I will check Craigslist today. You know that most she-males charge money. I am willing to split the cost with you."

Ray scoffed, "No, not fine. I do not pay to get my rocks off. You need to find a chick with a dick to meet us, and one that does not charge. I want to see her sucking your cock; I take her from the rear. Then I want to see her cock fucking your ass."
After Ray's phone call, I started my search on Craigslist for a chick with a dick. I found several and sent them all an e-mail. The next day, I received an e-mail from Crystal, a thirty-five-year-old transvestite with silicone breasts. Crystal lived about thirty miles from the town I was living in. Crystal provided her phone number to call confirming our meeting arrangements. When I called her, it rang six times, and I wondered if I had the correct phone number. Finally, when someone answered the phone, I said, "Crystal, Roger."
Crystal answered in a low, soft whisper, "Oh, hi sweetie; I'm Crystal, so nice of you to call."

I did not want to catch her at a bad time, so I asked, "Crystal, is this a good time to talk?"
Crystal replied, "Sure Roger; I just got out of bed and fixing my first cup of coffee."
The conversation was going as planned, I continued, "So, are you OK meeting Ray and me on Friday night?"
Crystal stretching her words, "Oh yes sweetie; I have two holes that loved to be filled."

I was beginning to be excited about having a threesome with Ray and Crystal, but needed to check, not sure how to ask I blurted, "Crystal, I have to ask. Do you charge when you meet someone?"
Crystal replied, "Oh no sweetie; I am always free."
I replied, "Great Crystal, Ray and I are not looking for a professional, just someone who likes to meet men and have fun."
"I love to have fun, and with the two of you, there are more possibilities. I am versatile. Why don't you two meet me at my place, where I have my things?" Crystal said with a playful sound in her voice. Crystal continues, "Now Ray is the straight guy who wants to fuck me and you are a bottom which likes to give oral? Crystal continues by asking, is it OK for me to top you?"

I responded, "Yes that sums it up, and I also like to give oral."
The meeting was set for seven PM at Crystal's house on Friday night. I sent Ray a text message giving him Crystal's facts. 'Thirty-five TV, 40D, seven inches cut, versatile.' Crystal provided a photograph that showed that she had large silicone boobs and a male member, a chick with something extra. Ray was all excited about meeting Crystal. The plan to meet as threesome was set.
On the Thursday evening, Ray calls me saying, "Roger, bad news my meeting has been canceled. I will not be arriving until Monday."
I said, "No problem Ray, I will reschedule."

I called Crystal to update her on the change of Ray's arrival date. She apologized, but she was going to be out of town on Monday and could not change her plans. I called Ray back and I told him, "Ray; Crystal will be out of town on Monday night. She cannot change her plans. Looks like it is going to have to be, you and I"
Ray, in an upset and loud voice, said, "Roger, you will have to find another, she-male."

Taken aback from his outburst and demand, I said, "I have tried, there are none available. I did find one, but she wants two hundred dollars an hour.
Ray retorted, "I am not paying for anyone's service; I want to meet a cock sucking she-male slut, or cross-dresser will do."

I apologized for not being able to meet his needs, "I have looked on Squirt and on Craigslist, and I'm telling you on short notice, I can't find someone." I started to be perturbed with his demand and in frustration I said, "Look, what you want me to do, wear pantyhose for you?"
Ray paused, with a devilish sound in his voice he said, "Yeah, you do that, you dress up for me."

I was jesting, was not inclined to play dress up for anyone, not even Ray. I tried to talk my way out of his demands, by offering an excuse, "What, are you kidding, right? I have never dressed, ever. You have to be crazy to want to see me in pantyhose. Ray, I don't have any pantyhose to wear."

Ray insisted, "Well, go out and buy some pantyhose. While you are at it, get a matching bra and panty set. Make it something sexy."

I continued to offer every objection not to dress, but Ray continued to press the demand. Resigned by his persistence, I agreed, "Well all right; I will find pantyhose, panties, and a bra. I am not going to buy a wig and a dress, or wear makeup, OK."
My agreement to play dress up for Ray excited him about our meeting. Ray urged me on by saying, "Yeah that will be fine; I want to feel nylon stockings rubbing on my legs." Ray agreed I would wear pantyhose and anything else I could find on short notice. I would meet him at his hotel room Monday night at seven PM.

I went to Walmart that Saturday. Walking around the woman's department, spying at the panties and bras' sets from a distant, my heart was pounding. I felt self-conscious about the thought of buying woman’s clothes. Someone from work or my church might see me with large woman garments when they know my wife is small. I knew that husband's shop for their wives, so why would anyone notice or care what I was buying.
Embarrassed, I walked down the panty display, grabbed a red lace ruffle panty with matching bra. Next, I walk to the stockings and selected several pantyhose; I made sure they were large. I raced to the automatic checkout; I did want a cashier to remark what I was buying. Quickly, I left the store. Five minutes later, I could still feel my heart pounding. I had an Adrenalin rush caused by buying woman garments as directed by a stranger named Ray.

In my e-mails and chats with Ray, we talked about me giving him blowjob while I was dressed in pantyhose, panties and a bra. Ray called them sissy clothes. The date, time was set, and everything confirmed; I would wear the pantyhose, panties and bra. I would rub my nylon-clad legs against Ray's legs, and Ray would get hard. I would perform fellatio for him, and we would both be happy.

Ray arrived on Monday and attended his business meeting. I got a call from him about six PM, Ray questioned, "Are you ready?"
I replied with an excited voice, "Sure, I'm ready to meet you and can be there at seven."
Ray continued, "Do you have sissy things on now?"
I responded with sound of humiliation in my voice, "No; I was going to get dressed at your motel room."
Ray shot back quickly, "No-good. I want you to arrive with your wear your sissy things."
I tried to offer my objection by saying, "No way; I do not want anyone to know."

Ray in a convincing voice, saying, "Who is to know, wear your stockings, panties and bra on, then your pants and shirt; no one will notice." Ray says, "I want you to arrive with wearing your sissy things. No sissy things, I will cancel our meeting."
I did not want to disappoint him, I reluctantly said, "OK I will. I will do as you ask. It should not take me long to get them things on."

Now Ray ordered me, "When you arrive, the door will be open, you knock, and I will go into the bathroom, you enter and remove your shirt and pants. When I walk out I want to see you in pantyhose, panties and bra."
Submissively, I responded, "Ok; I'll be there at seven."

I got naked and took the pantyhose out of the package. The package said they were large, but looked small. I looked if there was a front or back. I could not tell. I looked for instruction, there was none. The pantyhose were black and sheer. I asked myself, how do you wear pantyhose, one leg at a time? I had to roll up the leg, slide my foot into the tip, then pull and unroll the stocking to the knee. I did the same for the other leg, I stood, pulled on each side so the pantyhose and covered my butt to the waist. I smoothed out any wrinkles in the stockings; I looked at my stocking covered legs. I commented to myself; I had pleasurable and womanly shaped legs. I shaved my legs so to look more feminine for Ray.

I put the panties on first then the bra. Ouch, the Bra was unyielding. I bought a large, but the straps pressed into my skin restricting. The bra around my chest restricted my ability to take a deep breath. I covered up my sissy things with my pants, shirt and shoes. I drove to Ray's hotel dressed in woman underwear and had the filling others watching. I prayed not to have an accident or pulled over by the police. You could not tell I was wearing pantyhose, panty, and a bra. Nevertheless, I was self-conscious about my sissy condition.

I did not want to be late, and arrived at Ray's motel before the scheduled time. I sat in my car, feeling how smooth and silky the pantyhose were against my shaven legs. The bra was still tight and restricting my breathing, or maybe I was excited about being dressed.
At seven o' clock, I arrived at Ray's motel room door. I knocked on the door; I heard an answer, "Come in." Pushing on the door, I found it unlocked. Once I entered the motel room, I closed the door behind me. As instructed, I took off my shirt, pants and shoes to reveal my male body wearing black sheer pantyhose, red ruffle panties and a red under wire bra. I do not have big breast, but the bra did giving the appearance that I had small breasts.

A stranger appears out of the bathroom with a towel wrapped roughly around his waist. He said, "Well helloooo, I am Ray."
We shook hands; I replied and said, "Roger."

I lifted my arms, and twirled, so he could see all of me. He sat on the bed and asked me to stand in front of him. The pantyhose were sheer and black, but you could see my moderate erection bulging off to one side. He undid the towel exposing his genitals. His cock was limp. He turned me around, so I was facing away from him. He pulled on my hips causing me to sit on his lap.

I was in the typical lap-dancing position; my butt was hovering above his crotch. Moving my butt in circles, I pretended to grind his package with my cheeks. I changed the pace. I switched to a revolving motion; I was simulating riding him in reverse cowgirl position. Looking back at Ray as I grinded against his body, I could see the grin on his face become a smile. Sitting for full-body contact, wiggling my bottom on his legs, and rocking back and forth on his male member caused Ray to be aroused. The contact between my pantyhose and his flesh did not take long to awaken his hardness between my legs.

I continued 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 my nipples. He got my nipples erect; I got his limp member erect.

He told me to sprawl on the bed on my hands and knees facing him. I did as ordered. I saw his erection for the first time and could see a cut phallic about six inches. He stood in front of me, placed his hands on each side of my head, pulled my head forward and down, directed me to give him oral. I opened my mouth; accepted his hardness into my warm wet mouth. I heard him moan and tell me how that feels good. He kept his hands on my head moving his hips up into my mouth, using his hands to restrict my moving.

Ray used my mouth for his pleasure for a few minutes, he stops and ordered me to stand. He slid my panties down to my ankles. He turned me around, forced me onto the bed, so my knees were on the edge, my hands starched in front; I am in the doggy position. He rubs his cock along my crack and tries to rip the pantyhose, but no luck. Ray rips hole in the pantyhose at a location in line with my anus. I did not expect to receive anal intercourse that night; I was only hoping for oral.

As he rubbed his erection on my pantyhose, aroused, he grabbed my hips and dry humped me. Ray forced me on my elbows, pulled my hips up. He positioned himself with his cock aimed at the hole in my pantyhose. He slides his cock through the pantyhose and touches my rosebud. I have had been anal a few times, and I know I need to relax and let him do what he was going to do.

I needed to relax for his shaft and gland head to slip pass my anal sphincter muscle. I relaxed more with Ray being able to insert his erection halfway into my man-cunt. I was tight and there was no lube; I had to reach behind me and spread my cheeks. With a last push, he was all the way in. Ray started to thrust in deep then slowly withdrawal.

He grabbed my bra began to squeeze, pinching my nipple at the same time. I tighten on his member inside me, gave him pleasure. The speed picked up; the thrusts were deeper, and each time I cried a moan of pleasure. Ray held my hips, so I could not move, and he climaxed was way up inside me. Everything happened so fast that I did not realize Ray did not wear a condom.

I collapse on my side, Ray rolling with me, his manhood still inside me. We lie there for a few minutes, when his relaxed cock slipped out of my now dripping wet anus. He patted me on my butt and said I was hot in pantyhose. He started to dress, mentioning that he had nothing to eat. He told me to stay dressed. I went to the bathroom to go clean up. I kept the stocking on, put the panties back on and wore the bra; I was dressed as a sissy under and a guy’s clothes outside.

We drove to a restaurant with my sissy thing under my clothes. We had a pre dinner drink, another dinner drink during dinner, and an after-dinner drink. Ray made comments about being able to see my red bra through my shirt, and the man at the bar was looking at me. Ray was joking, but I still felt humiliated and self-conscious about being dressed. Ray would say I was dressed in sissy clothes, and that it suited me. During dinner, Ray went on how sexy I was; he said I was an enjoyable lay.
After dinner, I was thinking I would go home, but Ray asked, "Do you want to come back to the motel room?"

Well, the story continues; we returned to the room; we did what we did before. I fell asleep and may be I felt Ray in me one more time, or it might have been a dream. The next morning Ray woke me with his morning woody; he used me again. I left the motel tardily in the morning, went to my place, cleaned up, and was two hours late arriving at work.

I received a text message from Ray, I have extended my stay another night, I want to meet you tonight.
I sent a text message back; sure, what do you want me to wear for you this time?