It had been three months since my wife went away for four days giving me the opportunity to be a free woman. I was missing that wonderful weekend of unbridled sex and cross-dressing. There were no more opportunities on the horizon leaving me quite hopeless. In my despair, I surfed the internet for porn and cross-dressing sites when I came across a site called “Joann’s Shop”. It had the greatest selection of clothing, wigs, undergarments, and breast forms I had ever seen before. They also had articles on hair care, skin care, dressing tips, nails, eyebrows, make-up, and many other items for cross-dressers along with a question-and-answer section and chat room.

As I looked through the articles, I found a link to “Joann’s Club Paradise.” I clicked on the link and was amazed. It described a place dedicated to cross-dressers. They could transform almost anyone into a woman and then stay at their motel, as a woman, with other cross-dressers. It seemed too good to be true. They had a complete video of the club, its activities, and the staff. There were also some before-and-after transformation pictures that were unbelievable.

One of the pages described how it could be visited in total discretion, using yet another link. I could go there under the guise of a fishing trip completely supported by “JCP, LLC.” I clicked on the link and found a site that had no trace of its true intention. It required a password that had to be created on the “Joann’s Club Paradise” site to prevent an accidental booking.

That evening during dinner, I asked my wife if she would mind me taking five days to go on a fishing trip. I showed her the “JCP” site. Without the password entered, it appeared as a fishing excursion. She said I should get away and enjoy myself, especially since she did not like fishing at all. I told her I would book it tonight.

I took my lap-top to our study and went to the “Joann’s Club Paradise” site. I created a password as instructed, then viewed the information on visiting. There were many options such as bringing my own girly clothes, buying them there, renting them, transformation services, and others. A $200.00 per day deposit was required for each day reserved. Everything would be charged to “JCP,LLC” on my credit card. I clicked on the link to the fishing site. There was a box for a promotional code where I entered the password. A calendar appeared with their open days. They were solidly booked for ten weeks. I selected the first available Monday-to-Friday block in the second week of September. There were a few options for transportation. I decided to fly there since it was at least a twenty-hour drive. It was going to be a long wait.

I continued to visit the bookstore, whenever possible, but it was often dead in the summer and I was becoming frustrated. September couldn’t come soon enough. At the end of August, I got a brochure from JCP showing the dates of my ‘fishing trip’ with some pictures of a cabin, boat, and people holding fish. There was a map of the regional airport indicating where to be picked up by their shuttle.

The night before my flight, I packed a bag with my normal clothes. I had an early flight to Atlanta, where I connected with a local airline to a regional airport. I was so excited. Less than five hours later, I was walking out of the small airport toward a van. A beautiful woman stepped out of the van and greeted me, introducing herself as Joann. I asked her, “Thee Joann?”

She answered with a chuckle, “Yes, thee Joann. Please, take a seat and read this brochure. We have one more passenger before we leave. It’s only a twenty-minute ride.” She put my bag in the back of the van. A few minutes later, a second man came, and she did the same. The brochure had a picture of Joann on the front with a history of her transformation. I couldn’t help but stare at her. I couldn’t believe she wasn’t a natural-born woman. The second page of the brochure had a check-off list of services to be offered by Joann’s Club Paradise. We arrived at the club before I could finish reading the brochure. Joann opened the door and led us to the check-in desk.

There were two women at the desk. The first greeted me, asking for my credit card and feminine name. I had used the name Jean at the motel room gang-bang six months ago, so I used that name, again. We discussed the various rates and I chose the all-inclusive option. She came back with a card which she explained was to be kept with me at all times. The name on it was Jean. Then she told me to follow her so she could give me a tour of the facility.

She showed me the reception area next to the check-in counter. There was a big fireplace surrounded by comfortable couches and tables. Then, we walked into the dining room where there were tables, a small dance floor, and a bar. From there, we walked outside. There was a large pool with lounge chairs around it, an outside bar connected to the inside bar, a fire pit, and a pavilion. We walked further back where there were two small secluded hot springs. Continuing back further there was a sandy volleyball court, bocce ball court, and bean bag tossing areas. It was a beautiful place. My guide explained that all of the women we’d seen, so far, were cross-dressers. It was unbelievable.

Our last stop was the salon on the second floor, located directly above the lobby, at the beginning of the hallway to the rooms. There were two women (I think) attending to two customers. She told me to check off my salon choices and leave it in the basket on the counter. She said Monday was one of the busiest days, so it could take a few hours for my appointment. I checked off the full-service option and left the brochure in the basket as instructed. Finally, she took me to my room in which my card was used to open the door. She told me the salon would call me on my phone shortly with my appointment time before she left.

I walked around the room. My suitcase must have been delivered during our tour and was sitting on the bed. There was a flat-screen television in the sitting area that could be watched from the bed. A channel guide was sitting on the table that listed several porn channels, a local station, and an internal Joann’s Club Paradise channel. I turned on the Joann’s channel. Joann, herself, hosted the channel which alternated between activities, rules, testimonials, salon options, clothing selections, and other segments of the club.

As I was watching, the phone rang. It was the salon. I had a two o’clock appointment. Since it was only noon, I decided to walk down to the dining room and get some lunch. The hostess sat me at a table with a middle-aged woman, or so I thought. When she responded to my introduction, her voice immediately gave away her true identity.

She asked, “How do I look? I just came from the salon a few minutes ago.”

I said, “You look beautiful, I thought you were a woman.”

“Let me guess, my voice gave me away.”

“Yes, it did. I guess I’m going to have the same problem.”

She asked, “What time is your appointment?”

I answered, “Two o’clock”

“Would you like to get together afterward? My name is Gail. We could practice on our voices and walking. I really want to get more comfortable as a woman.”

I agreed to meet her at five o’clock in the reception area. We ate lunch together and talked until I left for the salon.

At the salon, a woman greeted me at the counter. I showed her my Joann’s card and she swiped it in her terminal. Her name tag indicated her name was Amanda. She told me to come through the door into the salon. She handed me a box and instructed me to go into a small room, remove all of my clothing, put it in the box, and put on the robe hanging on the inside of the door. When I came out of the room, she took the box, marked it with my room number, and put it on a table. We walked into another room where there was a shower with no door, a toilet with a swinging door, a padded table, and a long counter against one wall.

She instructed me to remove my robe and hang it up on the wall. Then, she put on a pair of latex gloves and started rubbing some lotion over much of my body, explaining it was hair remover. She used another lotion on my face that she explained was a more sensitive facial hair remover. I was told to raise both of my arms straight up, as she applied some lather under my arms, before shaving them clean. Next, she had me stand in the shower while she wet some small towels and wrung them out. They were used to remove the lotion from my skin. As she wiped, all of my hair came off. Finally, she turned on the shower and told me to rinse off. My skin was smooth everywhere when I stepped out. She helped me dry off and had me lie on my back on the table.

“How would you like your pubic hair trimmed? Here are some pictures of the most common examples.”

I paged through the pictures before choosing a heart. She said it was the most popular choice. First, she used a pair of scissors to cut all of my pubic hair short. Then she used shaving cream and a disposable razor to shave my bush into a heart with the point just over my dick. Next, she trimmed my eyebrows, ears, and nose hair, before sending me back to the shower, again. She washed my hair twice and then used conditioner. After she helped me dry off, she instructed me to put on my robe and follow her to the hot tub room.

She started filling the one-person tub with water, adding some type of bath beads that smelled heavenly. When the tub was full, she turned on the water jets and had me sit and relax in the tub, as she went back into the main salon room to another customer.

Almost an hour later, Amanda came back asking, “How does that feel? It’s time to dry off and put your robe back on.”

I replied, “That felt great, my skin feels so soft.” She shut off the tub and let it drain as we went into the main salon room. I sat down in a styling chair in one of the three cubicles. A woman named Michelle was working on another person in the next cubicle. Amanda showed me some samples of nail polish colors, suggesting I choose a hot pink. I agreed and she did my toenails first, followed by my fingernails next. She told me I didn’t have long enough hair to style, so we would have to choose a wig. We walked to the big table in the center of the salon. There were over a dozen Styrofoam heads with different wigs on them. She suggested a simple short straight hair that would be easy to manage. It was great the way she helped me with every decision.

We went back to the chair where she fitted the wig on me. Then, she applied my make-up, eyeliner, eyebrows, and lipstick. The transformation was amazing; even I was looking like a woman. Next, we went into the clothing room to pick out my wardrobe. Amanda explained I could rent all of the clothing, except bras, panties, bathing suits, and breast forms. Those I had to buy, but I could keep them in storage if I planned to return again in the future. There was a twenty-dollar refundable fee for the storage service.

She suggested 38-C asymmetrical breast forms. Since she hadn’t steered me wrong yet, I agreed to her suggestion. Then, like a kid in a candy store, I picked out the clothes and intimates for my stay, setting and hanging them on a small cart as Amanda scanned them with a small gun. Then, we rolled the cart to the original dressing room where I started. I took off my robe as instructed and lay on the table. Amanda sprayed my chest and breast forms with some kind of spray adhesive. After a few minutes, she set my breast forms in place and told me to lie still for a few minutes.

She picked out my clothes for the evening while I waited. Then she told me to sit up and pulled a bra over the front of me from behind, clasping it in the back. She handed me a pair of the thong panties I picked out, saying, “From now on, you have to dress yourself. Let’s see how you look when you’re finished.” As I dressed, she explained that if I had any problems with my breast forms, wig, make-up, or anything, to come to the salon desk anytime from eight to eight for help. I put on the tight stretch jeans, white blouse, and flat shoes. I could see my red bra through the light blouse. It made me feel quite sexy. She said I should stick to the basics while I acclimated to being a woman. She suggested I wait until tomorrow to wear a dress.

I looked into the full-length angled mirrors after dressing. I couldn’t believe it was me. Amanda asked, “What do you think?”

I could only answer one way, “You’re the most amazing person in the world. I love you.”

“Save that for the boys,” she said. “You will need to practice walking, talking, and moving as much as possible. It’s a good idea to hook up with another CD, if you can.”

I told her I was meeting a gurl from lunch at five o’clock. She took me to the counter where she printed out a receipt for the salon and clothing. She told me to take the cart to my room, put my clothes away, and leave the cart in the hallway. I gave her a hug before asking, “I hope you don’t mind me asking this, but are you a woman?”

“Yes, I’m a natural-born woman. I’m Joann’s sister. I’ll give you a tip. Everyone’s card is color-coded. If it is pink, then the person is a natural-born female. If it is blue, the person has male genitals. If it is red, the person has had gender reassignment. Oh, by the way, don’t ask Michelle that question unless you want to get embarrassed. I will be seeing you around.”

I rolled my cart to my room and arranged my clothes in the closet. The box with my male clothes was also on the cart. I put them in the bottom of the closet. When the cart was empty, I noticed a coupon on it for an enema at the salon. I put it on the end table. It was almost five o’clock. I looked at myself in the mirror one more time before leaving the cart in the hallway and walking down the stairs to the reception area. Gail was sitting on a couch with her legs crossed tightly.

I said, “Hi,” realizing immediately that my voice did not match my new look.

She laughed, “It looks like we both need voice lessons,” in a poor attempt at raising her voice an octave or so. I sat next to her, leaning slightly, crossing my legs to the point that both my feet touched the floor. I felt so much like a woman sitting that way. Gail took my hand and we practiced talking for a while. A waiter offered us a glass of wine from his tray, which we both accepted. It was so exciting sitting and talking like women.

Around seven o’clock, one of the staff sat with us. She was another beautiful woman with a name tag with a blue background identifying her as Chrissy. She asked us how we were doing and if we wanted to meet some men tonight or if we wanted to spend some time getting more comfortable. Gail immediately answered that she wanted to wait until tomorrow to meet a man. While at first disappointed with her decision, I decided she was probably making a good move and agreed with her choice. Chrissy reminded us that the last seating for dinner was in fifteen minutes. She said she would check on us again a little later.

Gail and I went to the dining room, requesting a table for two. We had a light dinner and several drinks as we continued to practice our talking and movement. Afterward, we walked around outside to practice our walking. There were several gurls in the hot springs wearing bikinis. I so wanted to reach that level of exposure. Reaching the game area in the back, we decided to play a round of bocce ball on the lighted court. Halfway through our game, two men walked up and asked if they could get us a drink. I told them we were drinking wine.

They came back ten minutes later with a bottle and glasses. They introduced themselves as Tom and Vince. We asked them if they wanted to play a round of bocce ball, men against women. They accepted. Vince and I took the first play. I declared, “I will take red balls and you can have blue balls.”

He immediately responded, “Not if all goes well tonight.” We all laughed as we realized what I said. Vince threw the small white ball first. Then, I threw one of my red balls. Vince gave me some pointers on throwing the ball, followed by putting his arms around me from the back to show me how to move. We continued to touch and feel each other through the game. Tom was putting similar moves on Gail. I could see she was enjoying it as much as I was.

Toward the end of the game, Gail whispered to me, “Would you mind if I invited Tom up to my room?”

I replied, “Are you kidding me, of course not. I think Vince might just carry me to my room.”

Gail said, “I’ll meet you for breakfast at nine.”

When we finished the game, Gail and Tom said good night as they walked away arm in arm. Vince said he and Tom drove there this afternoon and could not get a room. I invited him to stay with me tonight, so we walked back to my room. As soon as we closed the door in my room, he gave me a big hug and a kiss on the lips. I started to unbuckle his belt, unbutton his pants, and pull them down. His dick was already hard, pushing the front of his boxers out. I couldn’t believe how big he was when I pulled his boxers down. My expression must have given away my surprise, prompting him to ask, “Do you like what you see?”

I answered, “Very much.” I put both of my hands on his huge shaft, moving them up and down it, trying to absorb the sheer size of it. When I looked into his eyes, I realized I was smiling from ear to ear. I never had such a wonderful feeling of anticipation in all of my life. There was no doubt in my mind this night was going to be monumental. I wanted to savor each step like the most expensive wine in the world.

Vince suggested I slip into something more comfortable. I pulled out a negligee from my top drawer and went into the bathroom. I removed my blouse and jeans first, concerned that my breast forms would fall out of my bra. The lacy matching bra with the negligee seemed to be pretty firm, probably made for cross-dressers. As it turned out, the adhesive kept my breast forms intact, probably to the point where I could have gone braless. Of course, I wouldn’t take the chance of anything going wrong at this golden moment. I put on the bra and changed my panties to the thin light lacy ones that came with the negligee, followed by the negligee itself. I was in heaven as I sashayed to the bed.

Vince was lying on his back in the bed. I got on the end of the bed, pushing his feet apart, making a space to kneel between his legs. Again, I held his giant dick with both of my hands, moving them up and down his shaft. I softly circled the head of his dick with my index finger, before moving it across his slit, hoping he would ooze out some pre-cum. It was dry, so I continued to stroke his dick with my left hand as I softly rubbed the bottom of his balls with two of my fingers on my right hand. I finally got a little sigh. After a few more minutes of the soft touch, he started to ooze a little pre-cum.

I moved my head down and put my tongue on the tip of his dick, licking the pre-cum. It was thick and sweet, just the way I like it. I licked around the entire tip, like I was licking a lollipop. I still couldn’t get over its size. I wasn’t sure if I was going to be able to get it into my mouth without my teeth rubbing it.

I opened my mouth wide and pushed my head down on him until I could feel the head against the back of my mouth. Normally, at this point, I would push hard, forcing it into my throat. Not this time. I tried using his dick like a tongue suppressor. Then, I tried to say ‘ahhhhh’. It was just too big and stiff to fit into my throat. I couldn’t get half of it in my mouth.

Sensing my frustration, Vince said, “I don’t think you’re going to go any further than that. Maybe we should try something else.”

Suddenly, I thought to myself: Am I going to be able to take this in my ass? This could be the fuck of a lifetime or a total failure. As I reached over to my night table, Vince intercepted my hand and slipped an individually packaged condom into it.

He said, “You’re going to need this.”

It was an extra-large size magnum condom. I ripped it open, removed it, and rolled it down his extra-large cock. It didn’t quite reach all the way to the base. I got out a tube of lubrication and squeezed a generous amount of it up and down his monster member. Then I pulled my panties down in the back and put the tube up to my ass, squeezing some into my asshole.

I lifted one leg over his body, straddling him, then I pushed back. I had to use my two hands to spread my cheeks to get him lined up for entry. There was an enormous pressure all around my anal ring causing some pain. Vince used his hands to help spread my cheeks. This helped. I slowly pushed back, feeling a sharp pain as his large hard head began to open my anal ring. I pulled forward a little, then back again. I wanted him in me in the worse way, but I knew it was going to take some time. I pushed and pulled for a few minutes, working him in a little more each time. He was still holding my cheeks apart.

I decided to try the slow steady approach again. I held my breath, closed my eyes, and pushed back slowly. The pain steadily increased. I could feel the slow stretching of my anal ring as the giant shaft pushed inside me. I felt like it was going to split me in two. Since I was pushing back, I could have stopped the intrusion at any time, yet I kept the pressure on, determined to tame this monster and claim victory. Just as the pain became almost unbearable, the head of his cock passed through my ring and into my colon. The intense pain turned into intense pleasure. There was a prolonged period of pure ecstasy as his shaft seemed to endlessly push up my ass. I could not only feel it sliding through my sphincter, I could feel it sliding along the walls of my colon. I never felt so fulfilled, or maybe just filled.

I let out a long moan as my eyes were still closed and my lips were pursed. When I finally opened my eyes, they met Vince’s eyes. He was smiling as he said, “Are you alright?”

I responded, “I am now. This is the biggest cock I’ve ever had inside me.”

Vince replied, “This is my first anal sex. A lot of women don’t like anal, and those who do are afraid to let me fuck them in the ass. You’re so hot.”

I lifted myself up slightly, pulling him out a little. Then I relaxed my legs, allowing the weight of my body to bury his beautiful cock deep in my ass, once again. I leaned backward, driving it in a little further, before leaning forward, pulling it out a little. I decided the best position was leaning forward, using my thigh muscles and knees to rock back and forth. He put his hands on my breast forms like they were real. I bent my arms that were supporting my upper body, increasing his pressure on my chest. Every movement I made gave me a sensation somewhere on my body.

I continued rocking back and forth as we looked into each other’s eyes. It was the first time I felt something beyond sex with a man. We watched each other as our facial expressions were constantly changing in sync with our heightened passion. I started to let out small moans of pleasure. I couldn’t make up my mind if I wanted to continue the current pace of lovemaking or increase to a lust-filled frenzy.

I decided to stay with the sensual movement, but with one change. Each time I pushed back, I tightened the muscles in my ass as I began to withdraw. This drove both of us crazy. It felt equally good moving in and out. My own dick started to harden, causing the tip of it to rub against Vince through my panties and negligee. I was terrified that this would turn him off.

I watched his facial expressions for a clue to his response when he smiled and said, “It looks like I’m not the only one turned on here.”

I thought to myself: how lucky was I to find this man tonight. He pulled me closer with his arms around my neck, forcing my dick tighter between us. He gave me a consenting look. I increased the speed of my back and forth motion. I could feel the temperature rise from the friction of his huge dick in my tight ass. Both of us were beginning to pant. I clenched my muscles gripping his cock tightly inside me. His hips started to push up and his arms forced me downward as he drove it up my ass with a steady force. He tensed up as he cried out, “I’m...I’m…I’m cumming!” I could feel him pumping inside me. My colon began to spasm, causing my own dick to shoot its load into my panties.

We both lay motionless for several minutes. I could feel him soften inside me. He was as big soft, as most men were when they were hard. Finally, I shifted forward, pulling him out of me. With the fullest feeling I ever had, came the emptiest feeling I ever had. I’m sure my asshole was still dilated as it felt cold as though it was exposed to the night air. I swung my one leg over Vince, lying with my back to his face. I knew some of my cum must have leaked through and I wanted to clean it off of him as quickly as possible. I licked his abdomen with my tongue, tasting a small amount of my cum.

Then, I saw the condom on his dick. There were some feces on the upper portion. He was deeper in my ass than anyone had ever been before. I grabbed the condom at the base and pulled it up, turning it inside out before he could see it. I rolled off the bed, stood up, and threw the condom in the toilet. I thought to myself, I should have gotten the enema, if only I’d known I was going to get fucked by the largest cock I ever had.

Vince was still lying on his back with his dick almost completely soft, covered with his cum. I couldn’t resist putting it in my mouth. Although soft, it still filled my mouth. It was slippery, wet, and tasty. I continued to treat myself to this oral dessert until his cock was completely clean. Finally, I asked, “How long are you going to be staying here at Joann’s?”

He replied, “I guess it depends on whether Tom and I can get a room. I don’t have to be back home until Friday.”

I quickly offered, “Oh please, stay with me. I’m meeting Gail for breakfast; let’s see how she and Tom got along.”

He replied, “Okay, if Tom can stay with her, I’ll stay here with you.” He went into the bathroom before returning and cuddling up with me. We both fell asleep.

In the morning, I woke up first and took a shower. I picked out a brief girdle panty that would allow me to wear a tight pair of short shorts with a halter bra and halter top. I put on a pair of sandals that exposed my toes. The bright pink color of my toenails and fingernails constantly reminded me I looked like a woman, which helped make me feel like a woman. I was reveling in my femininity.

Vince got up and took a shower as I fixed my hair and make-up. He came out of the bathroom with a towel wrapped around him saying, “I’m going to have to go to my car to get my suitcase so I can put on some clean clothes. I’ll have to put on my clothes from last night to go to the car.” He took off his towel as he picked up his pants from the floor.

I couldn’t stand there without touching his beautiful dick. I put both my hands around it and started lightly jerking him off. He put his hands on my shoulders as I looked into his eyes. I tightened my grip as I continued moving my hands up and down his shaft. After several minutes, I could see the pre-cum forming on the tip of his cock. I dropped down to my knees, licking the tip of its tasty syrup before taking him into my mouth. His hands were now on my head, holding it still, as he pushed his meat as far into my mouth as he could. I started gagging and choking. He pulled back, giving me a little apology. With my hands still wrapped around the base of his cock, I pulled him back in, to try again, only to gag some more. While I couldn’t get it in my throat, I was starting to work up quite a bit of slobber. As I repeatedly tried, I started making a familiar “gluck…gluck…gluck” noise that I often heard on the porn videos at the bookstore.

I think I was giving him a ‘sloppy blow job’. My mouth and his dick were wet and there were strings of slobber everywhere. His hands were still on my head, prompting me to keep going. I increased my pace, taking him in as far as possible. Then, I changed up and began sucking the head of his cock as I wagged my tongue up and down his vein. I could feel his grip starting to tighten on my head. He began to gasp.

Finally, he cried out, “Ugh, ugh, ugh, I’m cumming!!!” His vein pulsated as he shot the first load into my mouth. I couldn’t believe how warm it was. As I instinctively swallowed, I felt like I was taking a gulp of coffee. I could feel the warmth in my throat working its way down toward my stomach. My mouth was filling again. I had to swallow a second time to keep it from escaping. It was even hotter than the first mouthful.

As he subsided, I tightened my hands at the base of his cock and pulled them up his shaft to squeeze him dry of any remaining cum. I licked it as I pulled it free. The taste of his cum was all through my mouth and throat. This was better than my morning coffee.

He helped me to my feet. I stood there dazed and smiling. He went to the bathroom and peed, before putting on his pants, shirt, and shoes to go to the car. When he returned, he changed into some clean clothes. We went down to the dining room and sat with Gail and Tom. I asked Gail if she could go to the ladies' room with me. I asked how it went with Tom and told her my plan to share our rooms with them. She told me Tom fucked her brains out last night and she would love to spend the week with him.

She gave me a little kiss on the lips before saying, “I’m really having fun here. I’m so glad I came and I’m so glad I met you. By the way, your mouth tastes like cum.” I smiled at her. That was only our first night. We still had three more nights to go. I love Joann’s Club Paradise and know I’ll be coming back there many more times.