I am not sure if I should be embarrassed, ashamed, depressed about my condition. I do not look unwell; does it show? I look normal to my wife, family and co-workers. I wonder if they know about my disorder. If they do, why did they not tell me? Like most illness, they start slow and build up and suddenly, bang; right between the eyes it hits you. Maybe for years I suspected, but not wanting to admit that to me. I did not think my condition was serious, but I wanted to keep it a secret.
My secret is I am bisexual. Bing bisexual is not a mental disorder or illness in itself. How can cock sucking or eating pussy be illness? My bisexuality developed a little fetish; I like to dress in woman clothes when I meet a man for sex. For the last five years, I believed I was just a normal cross-dresser. An article on line about the psychology of cross-dressing stating anyone who dresses in the clothes of the opposite sex is classified as a transvestite. Transvestite is sexual disorder as describe in the Diagnostic and Statistical Manual of Mental Disorders DSM-IV.
Admit tingly I am a Transvestite, because I achieve sexual excitement by cross-dressing. Transvestite can dress for two different reasons; First reason would be to seek to intensify sexual excitement in intercourse. This is the reasons I dress. The second reason someone dresses as a woman if the person show signs of gender identity problem.
Transvestites are not necessarily homosexual, with many straight men only meeting females. Many straight men who dress have no desire to meet a bisexual or gay man. My fetish did not start until I was an adult and in my 50s. I dressed for the first time when I met a stranger for sex. Craigslist is an excellent place to post a personal advertisement to meet someone. My post was to the personal for Orlando, Fl under the erotic encounters, and meeting male for male. My post was short and to the point, 53married white male seeks male to give head, nothing in return. A few days pasted when I received an email from a stranger from San Diego.
His email stated, "Hi my name is Ray 35 straight white married, and will be visiting Orlando in a few weeks. I saw your post in Craigslist and wanted to know if you would like to meet. I am a straight man and not looking to give a blowjob, just appreciate my cock sucked. Hope that you would like to meet."
When meeting strangers from the Internet I like to exchange a few emails to make sure the man is serious about meeting, and that he is not a wacko person. Exchanging a few emails and asking a few questions, you should be able to decide if you like-minded and should meet. Wanting to make sure you are what the other person is seeking, making sure there will be no disappointment.
I responded, "Ray's thanks for your email and interest. I am interested in meeting you. I am fifty-three years old, 5'-10" and 210 pounds, about twenty-five pounds heavy but not fat. I am clean-shaven, short gray hair, glasses. I would like to make sure you are OK with my age and my height to weight, Roger." I have talked to many men on-line and, some had an issue with age and with the overweight. Some men are seeking a 'Ten' to let them suck their cock. I like to think I am a 'Three' to 'Five', on a 'Ten' scale. I might not stand out with admirable looks; many men said I gave excellent oral service.
I like meeting men and being their fantasy. Many straight, married men like to receive oral intercourse. With their eyes shut, they do not mind if it is a male or female giving them head. I am also a man and think I know what men like, a fantastic blowjob and then cumming in a warm, wet mouth, having the other person swallow your load. I offer a man a service, free of charge. I will suck their cocks, and they climax in my mouth then tell me to swallow.
Rays next email back said, "Roger, I do not care about your age or your weight; I need someone to suck my cock. My motel room will be available on Friday evening. Do you know any transvestite? I always had a fantasy about meeting a chick with a dick." Asking if I knew a Tranny was a strange question. It sounded that Ray wanted a threesome.
My next email to Ray, "Ray I do not know any she-males, but I can check around and will let you know. I had this need to suck a chick with a dick, or even maybe bend over and fucked by one."
Ray responded, "Roger did not know you were a bottom. It would be hot to fuck the. She-male while she blows you then watch her fuck you as you blow."
Ray and I were exchanging several emails daily. After exchanging phone numbers, my phone rings at work. It is Ray; I steeped outside for some privacy. First question after hello, Ray said, "Do you swallow or spit?" That was a direct question from Ray, but I understood why he is asking.
I responded boastfully, "I like letting a man shoot off in my mouth and having him tell me to swallow his load." By the sound of his voice, he seemed please with my answer.
Ray continued, "Good; I am a straight man, and not interested in sucking any cock. I like the sound of your posting you are what I need." Ray continued his questions; he asked, "Did you find a chick with a dick yet?" I received his email last late last night and had not started looking for a Tranny.
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 fancy seeing the Tranny sucking your cock; I take her from the rear. Then I would like to see her cock fucking your man-cunt." Ray was graphic about what he wanted. From our conservation, it appeared the sight of a man in woman clothes turned on Ray.
Remembering a few years back, I met a man and a Tranny for some wild, passionate sex. If Ray wanted a threesome, I was going make that happen. After Ray's phone call, I started my search on Craigslist for a chick with a dick. I found several in the local area, sending them all an email. The next day, I received an email 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; so nice of you to call. What can I do for you?"
Not wanting 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 fixed 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; both of my holes loved to be filled."
I began to be excited about having a threesome with Ray and Crystal, but needed to check one thing, not sure how to ask I blurted, "Crystal, do you charge when you meet someone?"
Crystal replied, "Oh no sweetie; I am always free."
Glad that Crystal was not a professional, and that she was what Ray was seeking, I replied, "Great Crystal, Ray and I are not looking for a professional, just someone who likes to meet men and indulge in some fun."
Crystal responded, "I love having 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 keep 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 head?"
I responded, "Yes that sums it up and I also like to give head."
The meeting scheduled 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 has 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 called saying, "Roger, bad news, my meeting has been postponed. I now will be arriving on 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 likes is going to be, you and me."
Ray, in an upset and loud voice, said, "Roger, you will come up with another She-male."
Taken aback from his outburst and demand, I said, "I have tried, I can not find one available. I did find one, but she wants two hundred dollars an hour.
Ray retorted, "I am not paying for anyone's service; I desire 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 asking 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; I was not inclined to play dress up for anyone, not even Ray. I tried to talk my way out of his demands. I said in protest, "Right, What are you kidding? I have never dressed, ever. You have to be crazy to see me in pantyhose. Ray, I don't own 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 need 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 the Saturday. I walked around the woman's department, spying at the panties and bras' sets. My heart was pounding. I was self-conscious about the thought of buying woman clothes. Someone from work or my church would see me with a large woman garments when they know my wife is small. I know that husband's shop for their wives, so why anyone would 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 picking up several pantyhose; I made sure they were large. I raced to the automatic checkout; I did need a cashier 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 emails and phone calls with Ray, we talked him receiving a blowjob from me. He directed me to be 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 his 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?"
Replying with an excited voice, "Sure, I'm ready to meet you and can be there at seven."
Ray continued, "Are you wearing your 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 insist you to arrive with you wearing your sissy things."
I tried to offer my objection by saying, "No way; I do not care for 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, "You arrive wearing your sissy things. No sissy things, I will cancel our meeting."
Not wanting 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 ordering me, Ray directs, "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 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 could not tell if there was a front or back to the pantyhose. I looked for instructions, there was none? The pantyhoses were black and sheer. I rolled the stocking up one leg, sliding my foot into the tip, then pull and unroll the stocking to the knee. I did the same for the other leg. Standing pulled on each side, so the pantyhose pulled over my thigh. Wiggling my bottom and doing a little dance with my hips, pulling the pantyhose over my butt to my waist. Smoothing 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 look feminine to Ray because I shaved my legs. 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 wear 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 be in 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 like to be late, and arrived at Ray's motel before the scheduled time. Sitting in my car, I could feel how smooth and silky the pantyhoses were against my shaven legs. The bra was still tight and restricting my breathing, or maybe I was excited about dressing dressed. At seven o' clock, I was 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 sport large breast, but the bra did giving the appearance that I had small breasts.
A stranger walks 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 pantyhoses were sheer and black, but you could see my moderate erection bulging off to one side. He undid the towel exposing his genitals. His dick 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 change the pace. I switched to a revolving motion; I was simulating riding him in reverse cowgirl position. Looking back at Ray as I grind 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 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 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. Standing in front of me, he placed his hands on each side of my head, pulls forward and down, so directing me to give him head. I open my mouth; accept his hardness into my warm, wet mouth. I hear him moan and tell me how that feels good. He keeps his hands on my head moving his hips up into my mouth, using his hands to restrict my moving. After a few minutes of Ray using my mouth for his pleasure, he stops and orders me to stand. He slides my panties down to my ankles. Standing, he turns me, forcing me onto the bed, so my knees are on the edge, my hands starched in front; I am in the doggy position. He rubs his dick along my crack and tries to rip the pantyhose, but no luck. He reaches for a pen and pokes a hole in the pantyhose at a location in line with my anus. I did not expect to receive anal intercourse tonight; I was only hoping to give head. As he rubs his erection on my pantyhose, aroused, he grabs my hips and dry humps me. He forces me on my elbows, pulls my hips up, and slides the gland head in the hold of the pantyhose up to my rose bud. I had 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 to help his shaft and gland head to slip past my anal sphincter muscle. I had to relax to allow Ray 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, giving him pleasure. The speed of his thrusts picked up, each time I cried a moan of pleasure. Ray held my hips, so I could not move, and his climax 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 dick still inside me. We lie there for a few minutes. His relaxed dick slipped out of my now dripping wet anus. He patted me on my butt and said I was hot in pantyhose. He told me to stay dressed. I went to the bathroom to go clean up. I kept the stocking on, putting the panties back on and wearing the bra; I finished dressing.
When I stepped out of the bathroom, Ray said with a smile, "Be careful out there, your red bra show through your white shirt."
I moved to the mirror on the wall saying, "No shit," but I could not see the red bra.
Ray laughed saying, "Do not worry Roger, I was just kidding. However, you are a real turn on with your sissy things. You are a good cocksucker not you are a good cock sucking bitch." The humiliating words stung. Ray continued, "The feeling of your nylon clad legs rubbing my cock, and that lap-dance, wow. I just needed that sweet ass of yours. I hope you did not mind, slut." I looked a Ray; he had a silly smile on his face. I responded, "Yes that was kind of hot. That was my first time to give a lap dancing. You felt good inside me, but you did not use a condom." Ray admitted, "Yes, I brought one and intended to use it, but you were so hot in the panty hose I just could not wait to fuck your ass. I hope you do not mind, I am clean."
I scolded, "You should have used a condom if you were going to shoot in me. But I am clean too." As I said this, I could feel his man juice ooze out, and entered the bathroom to clean up again.
I received a text message from Ray, "I want to meet you tonight."
I sent a text message back, "Sure, what do you fancy me to wear this time."