X.S.X Experiment

All characters are over the age of 18 years old.

*****

Hello. My name is Justine, and I'm a 25 year old single male whose fetish curiosity had finally gotten the best of me. My owner granted me permission to recount my story.

I started collecting Playboy magazines at an early age. When I had my first computer at the age of 18, the world of porn opened up to me. I visited different websites from straight to various fetishes.

My curiosity led me to explore being a cross-dresser. I found a place that specialized in transforming men into women. The owner was named Brenda. A TG that was 45 years old with 22 years in her field.

I spent about four hours with her. The first hour was spent removing all of my body hair by using Nair. After that, she did my make-up and then dressed me up as a school girl. When I looked in the mirror, I was in shock at what I saw. I could not believe how attractive I looked as a female.

Brenda asked if I wanted to be photographed, which I happily agreed. Casual poses soon led to erotic poses, which excited me. As I laid on the bed, panties around my knees, skirt lifted up; Brenda soon dropped her sweatpants, revealing her big cock. She climbed on the bed and soon I found myself sucking her cock. Naturally each time she slid her cock down my throat I would gag.

She took several photos of me sucking her cock. Eventually, I came all over my stomach yet Brenda still had not shot her load. When she was done sliding her cock out of my mouth, Brenda started stroking it in front of my face, without having to say anything, I kept my mouth open.

Brenda shot her load into my mouth and covered my face with her cum. She told me not to swallow. She took some more photos of me. She finally gave me permission to swallow, which was thick and salty. Yet I enjoyed swallowing it.

After changing back into a boy and taking a shower I sat with Brenda and chatted briefly with her. She complimented me on my cock sucking skills and was surprised to learn that it was my first time doing so. I told her that I watched a lot of porn and I tried to imagine myself being one of those girls.

After giving me a copy of the photos, she asked if I would be coming back. My response was "of course" and added that I would love to try on other outfits. We kissed each other goodbye and I went home and looked over the photos. I was still shocked, yet impressed with how I looked as a female.

A month later I made another appointment with Brenda. I inquired about the possibility of dressing as a bride. She stated that it was possible, but because it was an elaborate and expensive outfit, there were certain conditions that came with it.

The conditions were a non-refundable deposit, must wear outfit for minimum of four hours. The last condition was for the individual to have had a thorough enema cleansing. I accepted her conditions and would see her at the appointed date and time.

On the appointed date and time, I arrived at Brenda's home. She was dressed in casual clothing with a salon jacket. After we kissed and said hello, I went through the same process of removing my body hair. The make-up took longer than usually, then Brenda started to dress me up as a bride. Even though I had a slim figure, Brenda insisted I wear a bridal corset.

Then I put on a pair of white floral stockings that were held up by the corset straps; followed by putting on white lace panties.

After I put on a pair of 6 inch white platform heels, I was ready to wear the bridal gown. Once Brenda zipped up the back part, a bridal veil was placed on my head.

Brenda explained how I should lift the front part of the bridal gown when walking. We headed to the patio and started taking some eloquent photos, then we went outside.

Brenda had a lovely garden which she felt was perfect for taking photos. Standing on the grass in heels was difficult, but Brenda was within arms reach to catch me if I were to fall. She would often check my make-up, and do some touch-ups as needed. We also took some photos in front of the house. She assured me that the neighbors were okay with this. We even did a few photos of me walking across the street.

Finally, we headed inside and took some more photos of me heading upstairs. Once we were in the bedroom, Brenda started to take some pictures of me in sexy poses.

Having removed the bridal gown, I posed on the bed in various provocative positions. As I laid on the bed, with the veil covering my face, Brenda undressed then climbed on top of the bed. She took off my panties and laid on top of me. Her erect cock gently rubbed against mine. As she kissed my neck several times, I started to get more aroused, but my cock still could not measure up to hers.

Brenda asked me if I wanted to lose my anal virginity to her since I was already dressed as a bride. After saying yes, she had me turn around and had me get on my knees with my ass in the air.

Once I was in this position, she spread my legs further apart. Then she grabbed my arms and tied them behind my back. I felt a cool gel being rubbed against my asshole, then what felt like a finger was inserted, then two and then three. When Brenda felt confident that I was slightly loose, she grabbed my ass with both hands and slowly started to penetrate me. As she started to penetrate me, the feeling was both painful and pleasurable.

Eventually, Brenda inserted her entire cock inside me. At first, she started to fuck me slowly and softly. She then started to go faster and harder. The sound of our skin slapping against each other echoed in the bedroom.

Brenda told me how she hasn't cum in a month. I yelled out for her to cum inside me. She continued fucking me fast and hard, then Brenda finally came inside me. She continued to fuck me, but this time soft and slow.

As she slowly pulled out, I felt empty, like her cock belonged inside of me. When I relaxed my ass, her cum started oozing out of my ass and continued down to my balls. Brenda untied my hands then turned me over onto my back.

Laying on my back exhausted, Brenda started to jerk me off. Her rhythm was slow at first then picked up to a faster pace. I yelled out that I was cumming yet she continued stroking me faster. As I came, she still was stroking my cock.

When my cock went limp, she released her grip. As I laid on the bed almost passed out, Brenda snapped a few more pictures of me. After coming to, Brenda helped me change back into Justin. We sat on the couch and chatted a bit. She hoped that she was not too rough with me. I told her no and that I actually enjoyed it.

Due to lack of coverage at work, I was not able to visit Brenda for about two months. I did chat with her by email and by phone when I had the time.

During my breaks and commute to work, I gave some thought about being a girl full-time but also as to what type of girl. My feelings were mixed, was cross-dressing just a sexual fantasy to satisfy my sexual urges or was this something I would be happy doing full-time? When coverage returned to normal, I asked Brenda about spending a full week with her: dressing and acting as different girls.

I asked if we could agree on a price. Her offer was $1,000 with some conditions similar to the bridal session; particularly, giving myself an enema. I agreed and made an appointment with her.

I arrived early Sunday with just the clothes on my back. Brenda greeted me at the door as she usually does wearing a bathroom robe.

We performed the same ritual of removing my body hair. Then I followed her to a small room. Upon entering the room, it looked like an examination room. I got on the examination table and she secured my legs to the leg spurs, then spread my legs as far apart as they could go.

She removed her robe to reveal her latex fetish nursing outfit. Without saying a word, Brenda had attached a chastity cage to my cock. She explained that wearing a chastity cage for a week was part of the condition to spend a week as a girl. Then she inserted a large butt plug inside my ass.

Brenda mentioned that when I agreed to lose my anal virginity, she knew that I was submissive and was confident that I will be just as submissive for the rest of the week. She was right, I was submissive.

Brenda told me to remember two phrases. the first one: "The yellow bus slowed down at the yellow light." This phrase was to be used if I needed to pause or get her attention.

The second phrase: "The zebra walked into the red sunset" was if I wished to completely stop the session. She also mentioned that there was no refund. I still agreed to her terms.

After helping me off the examination table, I was made to dress up as a maid. Brenda attached ankle cuffs with a short chain, which forced me to take short steps. A gag was placed in my mouth, Brenda said maids should be seen not heard.

Finally, I was made to wear ankle cuffs with a very short chain which forced me to take very short steps, half steps if you would. From Sunday to Tuesday, I learned the basics of being a maid for Brenda and served her. Late Tuesday evening, Brenda had me change from being a maid to being a slut. I was made to wear a micro-mini skirt, a small white tank-top, a pink garter belt to hold up my white stockings and red 6-inch platform heels.

Brenda placed a collar around my neck and locked it. With a large purse in her hand, I followed her to her car.

She took me to an adult bookstore. As we walked in, she chatted with the store clerk who then pointed to the back of the store. Once we reached the back of the store, Brenda opened the door to a small room. Inside the room was a sink, toilet bowel, and an old mattress.

From her purse, she took out a chain; on one end she attached it to my collar, then on the other end attached it to a hook which was attached to the wall. The chain was just long enough for me to lay on the mattress but not enough to leave the room. Brenda handed me a bottle of perfume and a stick of red lipstick before leaving the room.

For the time Brenda left the room, I had been servicing various men that came in and out of the room. There were times where I was servicing two at a time. After a while, I lost track of the numerous men I was servicing. I also lost all grasp of time from the lack of a clock and any windows. There were brief periods where no one had entered the room. I could only have assumed that it was because the store was closed.

As I laid on the mattress with ripped stockings, makeup practically non-existent, face covered in dry come and a gaping asshole with cum still oozing out, Brenda walked in. She laughed as she called me a filthy little sissy whore. After being freed by Brenda, I had a hard time standing up and walking. As I tried to follow Brenda, stumbling to try and keep up, I noticed the clerk hand her a thick envelope. When we reached Brenda's home, I was given a thorough enema cleansing, then she allowed me to take a long hot bath.

I got out of the bathtub as the hot water started to cool down. After drying myself and putting on a robe, I searched for Brenda. I found her and we discussed what had happened the past few days. She explained to me that these are the two most common requests other girls seek her out for. Brenda explained that I still had three more days left, but also offered me the option to leave without any consequences.

Four Months Later

It was four months ago when I had finished my week with Brenda, that I decided cross-dressing would be my calling. Sadly, I would not be able to travel on the path that I had chosen. An accident at work caused severe scarring on the right side of my face along with temporary blindness in my right eye. Having recovered as best as I could, I no longer felt confident that I would look passable. Brenda understood and accepted my decision.

I began my search for a lifestyle that would or could accommodate my injuries; which brought me to pony play. I continue my search for an owner/trainer to accept a new person but also one who understands and accepts my injuries.

The first few weeks were difficult because several have turned me down. Then sadly, no one replied to any of my requests. I was about to give up hope when I received a reply from a trainer named Ingrid, a 40 year old trainer. As I read her email she requested that before proceeding further I provide at least one reference. I sent her Brenda's contact and waited.

Two weeks later Ingrid replied back that my reference checked out and even highly recommended me to her. On the appointed date, I drove 2 hours to meet with Ingrid. As I pulled up to the gate I rang the doorbell and announced myself over the intercom. As I parked my car in front of the house and started walking towards the entrance, she walked out dressed in what appeared to be riding gear. After a brief introduction, I followed her into the house and we sat in her office and discussed my previous experience with Brenda.

Ingrid was satisfied with questions of my past experience, then she explained the expectation of me if I wish to pursue being her pony boy.

She stated that anyone who comes to her, seeking to be a pony boy, must spend a minimum of four days being pony boy.

I agreed to her conditions then inquired if it was possible to start today. Ingrid smiled then told me to follow her out to the back of the house. In the backyard I noticed a medium sized barn; inside were six stables that typically are used for horses. Then I was ordered to get into stable number three and undress.

Once undressed, Ingrid secured my arms behind my back with an armbinder. Then slid my feet into a pair of thigh-high pony boots which almost felt like wearing a pair of platform shoes but without the heels. A thick leather waist cincher was wrapped around my waist and strap; which had various rings on it. Ingrid secured a posture collar around my neck, followed by a leather head harness with blinders and bit gag.

She told me the safe phrase "the ponyboy left the barn" if I wanted to be free. Naturally the bit gag hindered my ability to speak clearly, so I nodded yes.

Over the next four days, Ingrid had me attached to some type of device that forced me to walk around in circles. At night, I slept in my stall on top of a pile of hay. My legs were in pain from the constant walking, especially in these pony boots where walking on the balls of my feet hurt the most.

By the fourth day, I waited to be freed by Ingrid, but I was sadly mistaken. Ingrid walked into the stable with another woman called Zelda. Zelda came into the stall and after briefly looking me over, handed her some cash.

Zelda attached a leash to the ring on the posture collar and led me to a small trailer. After being secured inside this small trailer, Zelda got into the truck and drove off. It was a very long drive, the various chains, kept me from falling over.

We arrived at some destination. As Zelda took me out of the trailer, I tried to utter the safe phrase. She laughed as she placed her hand on my face. She said that the safe phrase is no longer valid. Then took me inside her stable.

Once inside there were other ponyboys and even ponygirls in various stalls. After reaching my stall, I noticed a strange bench. After securing my legs on each of the leg portions of this bench, the rest of my body was bent over. My legs were spread as far apart as they could go.

Zelda told me to try and escape, but I could barely move or get up.

She crouched down and told me that I was attached to a breeding bench. After getting up, she snapped her finger and her stable girls escorted in about ten well hung stallions.

Each of them took turns mounting me, ramming their huge cocks in my ass deep and hard. They were rougher than the guys fucking me in the room at the adult bookstore. When each of these stallions finally shot their load inside me, it felt as if they had not cummed in months.

After the last stallion pulled out, my ass was gapping as cum started to ooze out of me. Zelda and the stable girls clapped their hands. I heard someone say they got over two thousands like from the live streaming. I was left in this position over-night.

In the morning a stable girl hosed me down with cold water, then left me to dry. Zelda came into my stall a few minutes later and released me from the breeding bench. Then took me to another stall where there were another set of stallions. After being forced to get on my knees, Zelda removed the bit gag and before I could say a word, the first stallion shoved his cock down my throat. He began throat fucking me, as I tried to free myself, Zelda held my head down.

I managed to gasp for some air between each stallion shoving their cocks down my throat. My mouth was filled with so much of their cum that it started oozing from my nose. When they were finally done, I was left on the floor alone throwing up. When I stopped throwing up, I tried to stand up, after getting my sense of balance I tried walking back to my stall. A few of the stable girls caught up with me then took me back to my stall and started to remove what I was wearing. I stated the phrase "the ponyboy left the barn" the girls started laughing, telling me that there are no safe words or safe phrases with Zelda.

Once naked, they gave me a sponge bath, hosed me down. After they dried me, they lightly coated my body in oil and had me put in a bright pink leather bodysuit followed by pink thigh-high pony boots, a pink head harness with a ring gag. Then my arms were secured in a black leather arm binder behind my back.

After double checking to make sure that everything was on and secured, one of them unzipped the back part of the leather suit. I then felt a very large butt plug with a pink tail, being inserted into my ass. I was then led to the far back of the stable and out into a large stall. As I was led inside, I saw the same breeding bench from before. They secured me to the bench, this time my upper body was leveled.

A short time later Zelda returned. She briefly told me of the lengthy conversations she had with Brenda. She continued stating that having me as a sissy pony has opened new doors for her to explore. Zelda mentioned how she notified all of the other pony trainers about me; her newly acquired sissy pony. She continued stating that as her sissy pony, I must be made available to service the ponyboys of other trainers.

Which is why I was made to wear a pink leather body suit and tied to a breeding bench. Zelda stated that my services are free of charge, as long as trainers are okay with their ponyboys being videotaped breeding me.

She snapped her fingers and soon one of the stable girls returned with a strange device that looked like clamps. Then it sounded like Zelda was talking to a camera as she gave a brief introduction I heard her mention me as her newly acquired sissy pony and as such, that I am to be gelded.

Before I knew it, the clamps were pressing hard above my balls; after holding down on them for what felt like five minutes, she released her grip.

Later that day, various trainers started to bring their ponyboys into the stall and let them mount me. At times I was even servicing two ponyboys at a time. I was reliving the days in the room at the adult bookstore all over again. It felt like days since I had last seen Zelda or any of her stable girls.

I was awakened by the blast of cold water from a hose. One of the stable girls was hosing me down, even my mouth. I tried to yell but the ring gag has left my mouth numb. Then I heard a brief exchange of words before hearing, "it's all yours."

And the process of being fucked by ponyboys continued, and then I passed out from exhaustion. The few times that I barely came to, I recall seeing a cock going into my mouth and feeling another in my ass. I finally woke up laying in bed staring at a ceiling, as I looked around it appeared that I was in a small room. When I tried to get up, a set of straps held me down as well as my arms.