Wendy and Clair The New Gurl
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How I Became A Gurl free porn video
This story is totally fiction, however, I wish it wasn't!.
I had been living with Candy for about a year when first I noticed it. I had never been what I would call hung, but felt like I was pretty average among men as far as cock size goes at about 6 or 7 inches.
Early in the second year of our relationship, I began to notice it getting smaller and smaller. This was a rather slow process at first, but by mid year it seemed to accelerate. By December it was down to nothing more than a nub. I had mentioned this to Candy on several occasions and finally, she said, “ I don't think it's anything to worry about, but if you are concerned why don't you see the doctor. Well, I was concerned so I made a doctor's appointment for the next day. Candy seemed very supportive of my plight and even volunteered to go to the doctor with me.
My doctor was at a loss as to why I was shrinking so much and so rapidly but speculated that it might be low testosterone so he gave me a prescription for a testosterone booster. Candy insisted that I let her go to the pharmacy and get the prescription filled and wanted me to just sit there and rest saying I had a rough day. In about half an hour she came back with a big bottle of pills and the instructions said to take one tablet night and morning.
I began taking my testosterone booster as my doctor had instructed and for a few weeks, I saw little to no change in the size of my cock. About a month into taking the meds, not only did I notice my cock was still getting smaller but my tits seemed to be growing, and growing rather fast. I then thought it time I needed to make another visit to my doctor before this go out of hand.
He examined me and agreed that my penis was still shrinking and my boobs were growing He added another prescription and when Candy came back with them. They looked a lot like aspirin.
By the end of winter of that year, my cock had shrunk to the point it was nonexistent, actually looked more like a deformed pussy than a cock and my tits had grown to the point I was having trouble hiding them. A few weeks earlier I had gone as far as buying a couple of pairs of overalls thinking the bib would help conceal my boobs.
I had been lucky in life and had a great job and was able to put away some money and retire at 50. Candy worked 3 days a week in a pharmacy, not because we needed the money but she said she just wanted to get out of the house. At that time we lived in Lenexa Ks but was planning to move to the Chicago Illinois area where Candy grew up as soon as we found a house we liked.
Our Realtor in the Chicago are called and told us she thought she had found the exact house we were looking for. This was a planned move and since Candy had grown up only a couple of blocks from where this house was she was super excited, so we decided to make the trip to Chicago and look the house over. The Realtor had all the inspections already done and everything checked out fine. We both agreed that we loved the house so we bought it and planned on putting our house in Kansas on the market as soon as we got back home.
Candy always slept naked but we hadn't had any kind of sex in close to a year other than me eating her pussy. That night she had laid her bra and panties on the foot of the bed when she got undressed. After laying there for a few minutes she asked, “Honey, would you do something for me”? Without thinking, I said” Sure, what is it”? I had noticed when she got undressed that the thong she was wearing looked a little big on her, and she replied “Put my panties on, pleeease”! With some hesitation, I got up and picked them up and put them on. I had no more got them on and straightened up when she said Those look great on you! Will you put my bra on too? I bet you can fill it nicely, I did as she asked and she complimented me on how well I filled out her bra and how sexy I looked.
At this time the real estate market in Lenexa was a bit on the slow side and the Realtor speculated that it could take between 8 to 10 months to find a buyer and close the deal.
We had discussed it and decided to stay there until it sold, then hire a moving company. She had friends who lived next door to our new house and they said they would check on it a couple of times a week for us until we could move in.
Over the next few weeks, she kept asking me to put on her panties and bra, and after about three weeks she even bought me two bras and 4 or 5 pairs of panties. As the days went by she was asking me to wear panties and a bra for longer periods each day. After about a month I was wearing them all day and even under my male clothing when I went out for something.
To be honest, I have been curious about wearing women's clothing for a long time but just too chicken to actually do it. About two months into waiting on our home's sale she dropped a bombshell on me. I knew she had went shopping that day but never asked any questions as to what she had purchased. Candy was pretty level headed on that and she didn't buy anything she couldn't put to use. She looked at me with a half evil smile and said the shopping trip I had today was for you! Wanna see what I got for you? I said Sure!
She went into the other room and came back with two big bags and what looked like two shoe boxes. She reached in the bag and pulled out a lady's top, which had lots of lace around the neckline. It was purple which she knew was one of my favorite colors. As she handed it to me, she said slip this on and let's see if it fits. By this time my boobs had grown to a D cup at least and it was near impossible to hide them. Once I slipped on the top, I was surprised just how well I looked in it. It fit just tight enough to show off my tits in a major way, but not so tight that it was uncomfortable. She reached in the bag again and came out with a pair of pantyhose. She said she would help me put them on for the first time so I didn't get a run in them and tomorrow she would help me shave my legs. Thankfully, I don't have a lot of body hair like some men, and it seemed that a lot of what I did have had disappeared along with my cock. That fact would make things much easier. Once I got the pantyhose on and looking okay she again reached in the bag and pulled out a black skirt. Once I got the skirt on she told me she had me a pair of lady's slacks, a pair of shorts, and a robe just like hers. She then reached for the second bag and pulled out this big box and handed it to me and told me to open it. When I did I found a wig with hair color very close to mine, a very dark brown almost black. She then informed me she had a makeup case and all the makeup we needed to transform me from male to female, and she even had a pair of flats and a pair of 2 inch heels.
Candy explained that she thought it would be much easier for me when we moved to just go through life as a woman. She said she knew it had to be embarrassing to have tits as big as mine had gotten as a man and I could actually flaunt them as a woman. Though I wasn't wild about the idea, what she said did make perfect sense.
Over the next few weeks, she would help me with my makeup each morning, giving me pointers and showing me what I did wrong and how to fix it. About six weeks or so before our house sold, we got up one Saturday morning and she said, Get ready and do your makeup, we are going to have a girl's day out. Up until that point I hadn't been out of the house much as a woman but had noticed Candy referring to me as Desiree more and more often.
We did have a great time shopping and even stopped at the food court and had lunch, something we hadn't done since my boobs began growing so much. We bought several new outfits for me and I remarked how happy I was that she came up with the idea of me being a woman full time
She said, Honey, I know how much you used to love sex, and just because your cock has shrunk to nothing is no reason you can't still enjoy sex, you just need to rethink things and do it more as a woman would. I was really hoping that when we moved you would agree to live as Desiree on a full time basis. I could get you a butt plug and I have this strap on dildo to help break in your gurl pussy before we move. Would you like that?
Once we move Steve and Sherry have agreed to help us. Steve has a small production company and produces porn movies. If we would like to be in one we can make as much as $10,000 each. For the last few weeks we lived in Kansas I wore a butt plug constantly and went up in size each Monday morning.
Finally, the big day had arrived and the moving company showed up right on schedule. Candy packed up two bags each and said she thought that would be enough to last until we got in the new house and found our other clothes. It was about 575 miles from our house in Lenexa to the new house in Chicago, so we decided it best to stop at a hotel in Springfield Il. for the night and make the remainder of the drive the next day. When we arrived at the new house Steve was there waiting and said why didn't we come to their house as Sherry had been cooking all day and since we would have no beds set up, we could just spend the night there.
When we arrived and went in I was a bit taken back when I saw Sherry. She was standing at the stove wearing nothing but a tiny white thong. Steve quickly excused himself and when he came back he just had on a pair of skimpy men's underwear. Candy had packed the purple robe that I always wore around the house. It came to just about mid thigh and was very sheer. My white g string panties and white lacy bra was very visible even when the robe was on and tied. Candy took off her dress, pantyhose, and bra leaving her in just a black g string. I wasn't too keen on us going out of our bedroom like that but Candy assured me it was okay. When we sat down to eat I got another surprise. Their table was just big enough for 4 people and instead of seating me beside Candy, I was seated between the two of them. Throughout the meal both, Steve and Sherry had their hands all over me, and what's more, I found that I loved every second of it! Once we all finished eating, Steve chimed in and said, I know you two have had a long day, but would you like to have a little fun before calling it a night? Sherry is just dying to get in Desiree's panties! Up to this point, no one had ever fucked me except Candy, and I found it strangely erotic that I was about to be fucked by the lady next door. Steve asked, do you two mind if I film this. Nothing will be released publicly unless both of you give the okay, it will be for the eyes of us 4 only, so we said Okay. After about 20 minutes of Sherry drilling my gurl pussy with her strap on, Steve said, Okay Sherry you have had enough for now, I need some of Desiree's pussy too. I had only had a dildo in my pussy up to then but when Steve's hard cock entered me. I thought I was going to pass out from the pleasure. As good as Sherry's strap on felt, Steve's cock felt even better! It felt so good that the little nub, which now was less than an inch erect, began to ooze cum.
Sherry looked at Candy and winked and said, Why don't you fuck Desiree and Steve can give her a mouth full of cock. I think she would look super sexy with both her holes filled, don't you?
As Candy pounded my gurl pussy she noticed cum was beginning to run down my legs from when Steve fucked me a few minutes earlier, so she subtly pointed this out to Sherry who was running the camera. About the time Sherry zoomed in on the cum running down my legs Steve exploded in my mouth. It felt as though he came a gallon as it was running out both sides of my mouth and dripping off my chin. I tried my best to swallow it all but there was just so much I couldn't. About this time Candy pulled out of me and I stood up straight. A little more cum escaped from my mouth and began running down my chest and between my titties.
Steve said, Why don't you two hit the bed, you are going to have a long day tomorrow with the movers getting here with all your furniture. If you still have some energy left tomorrow night Sherry and I will show you our playroom.
The movers showed up right at 9 AM and they got everything unloaded and all the bigger pieces put in place. Candy and I had talked during the day and decided to make it a point to call it a day early with all the moving as we both wanted to see this “playroom” Steve and Sherry had told us about. Candy had bought us several matching outfits on one of her earlier shopping trips. I took a shower and found a very skimpy pair of black g string panties and a black bra and over that, I put on a red tank top and black mini skirt and added a pair of 2” inch heels. Candy wore the same except she chose a white bra and panty set to wear underneath. With help from the movers, we had found most of our clothing and were able to take our shower and get dressed in our new house before going over to Steve and Sherry's.
We made it to Steve and Sherry's house just before 5 PM and rang the bell. Steve answered and invited us in. Wouldn't you know it, the first thing Candy said was, May we see the playroom now, Desiree is just dying to see it and so am I. Steve called to Sherry and told her we were going to the playroom and to come and join us as soon as she could.
The playroom was in their basement. It was a full basement just the size of their house. I am guessing around 2500 to 3000 square feet but was just one huge room except one partitioned off area next to the staircase which I presumed to be a closet. To the left of the staircase, I saw a St. Andrews Cross and some kind of St Andrews Cross modification. It looked like a St Andrew Cross attached to a huge wheel. There were sex swings, cuffs attached to metal bars suspended from the ceiling, stocks, and just about any dungeon device you can think of was in that room. What's more, there was a camera in the center of the room on all 4 sides and one in each corner. There was also a camera focused on each piece of equipment and some of them had more than one. Steve said, Would you two like to watch the film we shot last night? Before either of us could say yes, Sherry asked if we would mind if a couple of their friends joined us? She said I know we said this was for our eyes only and it can be if you want, but was just wondering if you two would mind some company. Candy and I looked at each other a bit perplexed but both said Okay to inviting them. Steve said they can be here in just a few minutes as they just live a few houses down from us. We all walked over to the opposite corner of the basement. There, they had a big screen tv, at least 65 inch and about 2 dozen theater chairs complete with drink holders. There was a soda fountain and popcorn machine just off to our right as well. It was no more than 15 minutes before the doorbell rang and Sherry went to answer the door. When Sherry returned she had a couple with her. They looked to be in the mid to late '40s. Ken, who was a dead ringer for Eric Estrada, and Jo Ann, was a really cute blond with a killer body and only wore a pair of Hooters shorts and a crop top. Sherry introduced everyone and asked them if they would like to sit in and watch a little movie the 4 of us made the night before They eagerly said okay!
I knew immediately things was about to start up again and that was fine by me. What tipped me off first was the seating arrangement. Candy, Jo Ann, and Sherry were seated on the front row, and me in the center on the second row with Steve to my left and Ken to my right. The movie hadn't been playing for 3 minutes when I felt a hand coming from my left inching it's way up my tiny little skirt. I opened my legs to give him a little better access. About the time I did that I felt another hand coming from the other direction going up under my top. About the time the hand under my top slipped my bra up exposing my bare titties Steve whispered in a very low voice, Aren't you the little whore? Inviting guests over to see you get your gurl pussy pounded and your mouth filled with cock! Then Ken said to Steve, Do you think we need to punish the little whore? Maybe she needs to be put on the wheel or maybe even put in the stock and then see how she likes the fucking machine. Steve said, yeah, that's a great idea, she can even take turns sucking us off as she takes that big dildo. All 3 of the girls are bisexual and they had their own thing going on the front row, but I couldn't concentrate on them for Ken and Steve. One of them, I am not 100% sure which finally got his hand positioned in such a way as to get a finger in my gurl pussy and that was all it took to send me over the edge and I lost all track of time.
The next thing I knew the movie was over and Ken grabbed me by the arm and said, Okay Slut, let's go. The big wheel was sitting on a spot where there looked to be a drain in the floor right underneath it. Steve had me step up on the two pedestals at the bottom of the wheel, but not before he told me to strip to my bra and panties. I am a very submissive gurl and find it near impossible to disobey a command from anyone. He strapped my ankles tightly to the wheel. This made my legs spread open wide. Ken took my left arm and strapped it and then did my right. This positioned my arms wide and above my head. This wheel was mounted on bearings so it spun easily and would turn on its own for a long time. The last strap Ken added went around my waist. Ken had no more than got the last strap buckled when Steve reached up high on the wheel and gave it a nice hard spin. It seems as though I was strapped to a car tire and the car running 55 mph! By this time both Steve and Ken had dropped their pants and underwear and had their cock in hand. About the time I thought what are they going to do, two streams of water began hitting me! Oh, My goodness, they are pissing on me. By the time they finished, I had piss in my mouth, my ears, and even up my nose. Steve stepped on a pedal to the left side of the wheel and it began slowing down, and finally came to a stop with me upside down. Ken turned the wheel so I was back right side up and began unbuckling the straps. I was drenched in piss and so dizzy I couldn't even stand without assistance from both Steve and Ken.
Ken looked at Steve with an evil smile and said, should we give her a taste of the machine? Steven and Ken walked me over to this thing that looked like a small table and at the end, it had cutouts for my neck, and wrists and when I placed my neck and wrists in the cutouts, with their assistance there was another part with matching cutouts that came down and latched so it was impossible for me to get my head or arms free. Once in this position, I could only see things directly in front of me but felt someone grab my panties and pull them down to my ankles. Next, I felt a hand on my ass and near my gurl pussy, then felt something cold on my pussy, and then what felt like two fingers enter me. I then felt something cold touch my pussy for a few seconds then push its way inside me. By this time both Steve and Ken were only semi dressed, neither had anything on from the waist down. Steve was nicely hung with around 7 inches but Ken had closer to 9 or 10. I assumed whatever I felt enter my pussy was the machine they were talking about as it began to pump my tight hole. It pumped me very slowly at first but after a time began to gradually gain speed. Ken walked around in front of me and put that big thing near my mouth. I struggled to reach it but couldn't quite get it in my mouth. Finally, he gave it to me and I sucked him as the machine pumped my horny hole. It didn't take too long before I could tell Ken was on the edge of cumming. I was so excited thinking he was going to fill my mouth with his jizz, but just about then he pulled his cock from my mouth and filled my face full. Just a few moments later Steve stepped in front of me and his cock looked rock hard too. I sucked him off as well and got another splash in my face for my efforts. The fucking machine they were using on me dispensed lube ever so often and kept my pussy nice and lubed but it had been going for a time now and my little hole was beginning to get sore when Steve stopped the machine and pulled the dildo out of me.
While all this had been taking place the 3 girls had their own fun, fucking sucking and eating each other. Jo Ann came over to me and said, why don't you and Candy call it a night, you have a lot to do tomorrow to get things all squared away in your new house. I will give you something to look forward to though. Be back here tomorrow night at 6 PM sharp, we have a big surprise for the two of you that we are sure you will love! We said our goodbyes and headed back to our house. I am not sure if any of our new neighbors were watching but I am quite sure I was walking a little bit funny after the pounding my gurl pussy took from the machine and both the guys.
The next morning came too quickly but we got up and began our task of getting the
the house in order. About 4 Candy said let's call it a day, and get ready to go over to Steve and Sherry's. I am just dying to find out what kind of surprise they have for us. Sherry took her shower and while she was getting dressed I took mine. I sometimes still needed a little help with my makeup to make it look like I want it to look, and that way she was able to help me. We opted to wear some Hooters style shorts and a purple top. My shorts were white and had SLUT written across the ass and Candy's was black and had Bitch written on them. Since our shorts were rather risque, we decided to go out our back door and go a couple of hundred feet over to their house since that area wasn't as well lit. We rang the bell and this time Jo Ann answered the door and said, come in girls we have been waiting for you! As we started down the stairs to the playroom Jo Ann said, I know your pussy took an awful pounding last night, I hope it isn't too sore for some fun tonight as she grabbed a big handful of my left ass cheek. I replied, Of course, I am ready for some more fun
When we got to the bottom of the stairs I was aghast! Every seat in their theater, all 24 of them were filled and what's more, they were watching me get my pussy drilled by that machine. I could tell that they had seen everything that transpired the night before and were very near the part where we decided to call it a night. Within two or three minutes the movie ended and everyone got up and came over to us and seemed anxious to meet the star of the movie they just watched. None of the men had on anything more than very skimpy underwear and a couple was completely naked. None of the women had on more than a pair of G sting panties or a thong. Jo Ann said, Why don't you two take off your top and shorts, get comfortable and I will introduce you to everyone. Jo Ann introduced us, one couple at a time, and told me they were all members of The Bottoms Up Sex Club of GreaterChicago and all of them lived within a block or two of our house.
Now I had already had one shock when I came down the stairs and saw all those people but by far the biggest one was yet to come. Candy looked at me and said, Come over here sweetheart, we need to talk. I followed her to a table and she began by saying, As you know I grew up here and lived here up until shortly before you and I met. My mom and dad were co-founders of Bottoms Up. When we met, I thought I could give all this up but found it wasn't possible for me to do that. She then confessed to giving me estrogen instead of the testosterone I thought I was taking. I have known most of, these people since we were all k**s, and I knew in advance everything that has happened. That said, you have every right to leave me and never look back but I am hoping you don't. I was fighting mad for a few moments but then it hit me, why should I be angry? I have had the time of my life since all this started and told her so, and that I was okay with it all, just wished she had gone about it a bit differently. Once Candy raised her hand with the thumbs-up sign everyone let out a cheer that I am sure the whole neighborhood had to hear.!
Sherry came over and said, now that everything is out in the open, are you ready for your initiation ceremony to become a full member of Bottoms Up? Thinking I had come way too far to turn back now, I said yes. Sherry said, Well then, I'll let Miss Jo Ann explain everything to you.
Okay Desiree, let me first say every woman in this room has been through this process at one time or another, and yes, that includes your wife. Do you see the door over behind the staircase? In that room is a photo of each and every girl here except you taken just seconds after this process is complete. Yours will soon be there as well. Now I'll try to explain the process. All the male members will form a line. This is one reason I had you to take off your top and shorts. The first man in line will walk up to you and begin jacking his cock. As he stokes he will tell you where he wants to shoot his load, and what position he needs you in to do it. He is free to select any part of your body he wants as his target, ass, titties, face or where ever he chooses. You will do your best to get in the position he wants and then he shoots his cum where ever he stated he wanted to. Then the next man in line does likewise and this continues until you reach the end of the line. Once the end of the line is reached, Ken or I will come and take a photo of the cum drenched Desiree and we will frame it and it will assume it's it's rightful place alongside all the other girls. Do you understand all this? Do you have any questions?
I said I do understand, but I also have a question. Let's just say I was entering the club as a man, is there an initiation? Jo Ann looks over at Ken and says, You want to take this one? Ken says sure. Yes, there is an initiation for men too, and every man here has been through it just as the ladies have been through theirs. It goes like this. There is a hat in the room Jo Ann showed you earlier. Under it is strips of paper, each one identical to the other in every way. Each female here will write her name on a strip of paper then fold it in half three times and drop it in the hat. Once all the girls have their name in the hat, the male inductee draws one strip of paper and reads the name aloud, then strips completely naked. The inductee is then seated in the room and the door is closed. Whichever girl is selected by the name draw will then approach the room with a digital camera. She then opens the door, enters, and closes it behind her. She can then do anything she wants to make his cock hard, but can't touch him. At the end of ten minutes, a timer sounds and, she snaps a photo of the guy's cock. Now for the fun part. The photo is then judged by all the other members male and female and a vote is taken as to whether she made him sufficiently hard or not. If she fails to make his cock hard the guy is accepted and no further action is taken, but if she succeeds, the guy must then draw one more name from the hat. That girl approaches and has the inductee to bend over and grab his ankles. She is then given a leather belt and is instructed to strike his bare ass with the belt 5 times and do it as hard as she likes. There is one footnote to this, so far, no man here as made it without getting a smack on the ass with the belt.
My initiation went off smoothly, but I was a mess when they finished. There were 14 men total and 7 chose to cum on my face, 4 chose to cum on my titties, and 3 wanted to cum on my ass. When you enter the room and look at the back wall, my photo is 3rd from the left.
I had been living with Candy for about a year when first I noticed it. I had never been what I would call hung, but felt like I was pretty average among men as far as cock size goes at about 6 or 7 inches.
Early in the second year of our relationship, I began to notice it getting smaller and smaller. This was a rather slow process at first, but by mid year it seemed to accelerate. By December it was down to nothing more than a nub. I had mentioned this to Candy on several occasions and finally, she said, “ I don't think it's anything to worry about, but if you are concerned why don't you see the doctor. Well, I was concerned so I made a doctor's appointment for the next day. Candy seemed very supportive of my plight and even volunteered to go to the doctor with me.
My doctor was at a loss as to why I was shrinking so much and so rapidly but speculated that it might be low testosterone so he gave me a prescription for a testosterone booster. Candy insisted that I let her go to the pharmacy and get the prescription filled and wanted me to just sit there and rest saying I had a rough day. In about half an hour she came back with a big bottle of pills and the instructions said to take one tablet night and morning.
I began taking my testosterone booster as my doctor had instructed and for a few weeks, I saw little to no change in the size of my cock. About a month into taking the meds, not only did I notice my cock was still getting smaller but my tits seemed to be growing, and growing rather fast. I then thought it time I needed to make another visit to my doctor before this go out of hand.
He examined me and agreed that my penis was still shrinking and my boobs were growing He added another prescription and when Candy came back with them. They looked a lot like aspirin.
By the end of winter of that year, my cock had shrunk to the point it was nonexistent, actually looked more like a deformed pussy than a cock and my tits had grown to the point I was having trouble hiding them. A few weeks earlier I had gone as far as buying a couple of pairs of overalls thinking the bib would help conceal my boobs.
I had been lucky in life and had a great job and was able to put away some money and retire at 50. Candy worked 3 days a week in a pharmacy, not because we needed the money but she said she just wanted to get out of the house. At that time we lived in Lenexa Ks but was planning to move to the Chicago Illinois area where Candy grew up as soon as we found a house we liked.
Our Realtor in the Chicago are called and told us she thought she had found the exact house we were looking for. This was a planned move and since Candy had grown up only a couple of blocks from where this house was she was super excited, so we decided to make the trip to Chicago and look the house over. The Realtor had all the inspections already done and everything checked out fine. We both agreed that we loved the house so we bought it and planned on putting our house in Kansas on the market as soon as we got back home.
Candy always slept naked but we hadn't had any kind of sex in close to a year other than me eating her pussy. That night she had laid her bra and panties on the foot of the bed when she got undressed. After laying there for a few minutes she asked, “Honey, would you do something for me”? Without thinking, I said” Sure, what is it”? I had noticed when she got undressed that the thong she was wearing looked a little big on her, and she replied “Put my panties on, pleeease”! With some hesitation, I got up and picked them up and put them on. I had no more got them on and straightened up when she said Those look great on you! Will you put my bra on too? I bet you can fill it nicely, I did as she asked and she complimented me on how well I filled out her bra and how sexy I looked.
At this time the real estate market in Lenexa was a bit on the slow side and the Realtor speculated that it could take between 8 to 10 months to find a buyer and close the deal.
We had discussed it and decided to stay there until it sold, then hire a moving company. She had friends who lived next door to our new house and they said they would check on it a couple of times a week for us until we could move in.
Over the next few weeks, she kept asking me to put on her panties and bra, and after about three weeks she even bought me two bras and 4 or 5 pairs of panties. As the days went by she was asking me to wear panties and a bra for longer periods each day. After about a month I was wearing them all day and even under my male clothing when I went out for something.
To be honest, I have been curious about wearing women's clothing for a long time but just too chicken to actually do it. About two months into waiting on our home's sale she dropped a bombshell on me. I knew she had went shopping that day but never asked any questions as to what she had purchased. Candy was pretty level headed on that and she didn't buy anything she couldn't put to use. She looked at me with a half evil smile and said the shopping trip I had today was for you! Wanna see what I got for you? I said Sure!
She went into the other room and came back with two big bags and what looked like two shoe boxes. She reached in the bag and pulled out a lady's top, which had lots of lace around the neckline. It was purple which she knew was one of my favorite colors. As she handed it to me, she said slip this on and let's see if it fits. By this time my boobs had grown to a D cup at least and it was near impossible to hide them. Once I slipped on the top, I was surprised just how well I looked in it. It fit just tight enough to show off my tits in a major way, but not so tight that it was uncomfortable. She reached in the bag again and came out with a pair of pantyhose. She said she would help me put them on for the first time so I didn't get a run in them and tomorrow she would help me shave my legs. Thankfully, I don't have a lot of body hair like some men, and it seemed that a lot of what I did have had disappeared along with my cock. That fact would make things much easier. Once I got the pantyhose on and looking okay she again reached in the bag and pulled out a black skirt. Once I got the skirt on she told me she had me a pair of lady's slacks, a pair of shorts, and a robe just like hers. She then reached for the second bag and pulled out this big box and handed it to me and told me to open it. When I did I found a wig with hair color very close to mine, a very dark brown almost black. She then informed me she had a makeup case and all the makeup we needed to transform me from male to female, and she even had a pair of flats and a pair of 2 inch heels.
Candy explained that she thought it would be much easier for me when we moved to just go through life as a woman. She said she knew it had to be embarrassing to have tits as big as mine had gotten as a man and I could actually flaunt them as a woman. Though I wasn't wild about the idea, what she said did make perfect sense.
Over the next few weeks, she would help me with my makeup each morning, giving me pointers and showing me what I did wrong and how to fix it. About six weeks or so before our house sold, we got up one Saturday morning and she said, Get ready and do your makeup, we are going to have a girl's day out. Up until that point I hadn't been out of the house much as a woman but had noticed Candy referring to me as Desiree more and more often.
We did have a great time shopping and even stopped at the food court and had lunch, something we hadn't done since my boobs began growing so much. We bought several new outfits for me and I remarked how happy I was that she came up with the idea of me being a woman full time
She said, Honey, I know how much you used to love sex, and just because your cock has shrunk to nothing is no reason you can't still enjoy sex, you just need to rethink things and do it more as a woman would. I was really hoping that when we moved you would agree to live as Desiree on a full time basis. I could get you a butt plug and I have this strap on dildo to help break in your gurl pussy before we move. Would you like that?
Once we move Steve and Sherry have agreed to help us. Steve has a small production company and produces porn movies. If we would like to be in one we can make as much as $10,000 each. For the last few weeks we lived in Kansas I wore a butt plug constantly and went up in size each Monday morning.
Finally, the big day had arrived and the moving company showed up right on schedule. Candy packed up two bags each and said she thought that would be enough to last until we got in the new house and found our other clothes. It was about 575 miles from our house in Lenexa to the new house in Chicago, so we decided it best to stop at a hotel in Springfield Il. for the night and make the remainder of the drive the next day. When we arrived at the new house Steve was there waiting and said why didn't we come to their house as Sherry had been cooking all day and since we would have no beds set up, we could just spend the night there.
When we arrived and went in I was a bit taken back when I saw Sherry. She was standing at the stove wearing nothing but a tiny white thong. Steve quickly excused himself and when he came back he just had on a pair of skimpy men's underwear. Candy had packed the purple robe that I always wore around the house. It came to just about mid thigh and was very sheer. My white g string panties and white lacy bra was very visible even when the robe was on and tied. Candy took off her dress, pantyhose, and bra leaving her in just a black g string. I wasn't too keen on us going out of our bedroom like that but Candy assured me it was okay. When we sat down to eat I got another surprise. Their table was just big enough for 4 people and instead of seating me beside Candy, I was seated between the two of them. Throughout the meal both, Steve and Sherry had their hands all over me, and what's more, I found that I loved every second of it! Once we all finished eating, Steve chimed in and said, I know you two have had a long day, but would you like to have a little fun before calling it a night? Sherry is just dying to get in Desiree's panties! Up to this point, no one had ever fucked me except Candy, and I found it strangely erotic that I was about to be fucked by the lady next door. Steve asked, do you two mind if I film this. Nothing will be released publicly unless both of you give the okay, it will be for the eyes of us 4 only, so we said Okay. After about 20 minutes of Sherry drilling my gurl pussy with her strap on, Steve said, Okay Sherry you have had enough for now, I need some of Desiree's pussy too. I had only had a dildo in my pussy up to then but when Steve's hard cock entered me. I thought I was going to pass out from the pleasure. As good as Sherry's strap on felt, Steve's cock felt even better! It felt so good that the little nub, which now was less than an inch erect, began to ooze cum.
Sherry looked at Candy and winked and said, Why don't you fuck Desiree and Steve can give her a mouth full of cock. I think she would look super sexy with both her holes filled, don't you?
As Candy pounded my gurl pussy she noticed cum was beginning to run down my legs from when Steve fucked me a few minutes earlier, so she subtly pointed this out to Sherry who was running the camera. About the time Sherry zoomed in on the cum running down my legs Steve exploded in my mouth. It felt as though he came a gallon as it was running out both sides of my mouth and dripping off my chin. I tried my best to swallow it all but there was just so much I couldn't. About this time Candy pulled out of me and I stood up straight. A little more cum escaped from my mouth and began running down my chest and between my titties.
Steve said, Why don't you two hit the bed, you are going to have a long day tomorrow with the movers getting here with all your furniture. If you still have some energy left tomorrow night Sherry and I will show you our playroom.
The movers showed up right at 9 AM and they got everything unloaded and all the bigger pieces put in place. Candy and I had talked during the day and decided to make it a point to call it a day early with all the moving as we both wanted to see this “playroom” Steve and Sherry had told us about. Candy had bought us several matching outfits on one of her earlier shopping trips. I took a shower and found a very skimpy pair of black g string panties and a black bra and over that, I put on a red tank top and black mini skirt and added a pair of 2” inch heels. Candy wore the same except she chose a white bra and panty set to wear underneath. With help from the movers, we had found most of our clothing and were able to take our shower and get dressed in our new house before going over to Steve and Sherry's.
We made it to Steve and Sherry's house just before 5 PM and rang the bell. Steve answered and invited us in. Wouldn't you know it, the first thing Candy said was, May we see the playroom now, Desiree is just dying to see it and so am I. Steve called to Sherry and told her we were going to the playroom and to come and join us as soon as she could.
The playroom was in their basement. It was a full basement just the size of their house. I am guessing around 2500 to 3000 square feet but was just one huge room except one partitioned off area next to the staircase which I presumed to be a closet. To the left of the staircase, I saw a St. Andrews Cross and some kind of St Andrews Cross modification. It looked like a St Andrew Cross attached to a huge wheel. There were sex swings, cuffs attached to metal bars suspended from the ceiling, stocks, and just about any dungeon device you can think of was in that room. What's more, there was a camera in the center of the room on all 4 sides and one in each corner. There was also a camera focused on each piece of equipment and some of them had more than one. Steve said, Would you two like to watch the film we shot last night? Before either of us could say yes, Sherry asked if we would mind if a couple of their friends joined us? She said I know we said this was for our eyes only and it can be if you want, but was just wondering if you two would mind some company. Candy and I looked at each other a bit perplexed but both said Okay to inviting them. Steve said they can be here in just a few minutes as they just live a few houses down from us. We all walked over to the opposite corner of the basement. There, they had a big screen tv, at least 65 inch and about 2 dozen theater chairs complete with drink holders. There was a soda fountain and popcorn machine just off to our right as well. It was no more than 15 minutes before the doorbell rang and Sherry went to answer the door. When Sherry returned she had a couple with her. They looked to be in the mid to late '40s. Ken, who was a dead ringer for Eric Estrada, and Jo Ann, was a really cute blond with a killer body and only wore a pair of Hooters shorts and a crop top. Sherry introduced everyone and asked them if they would like to sit in and watch a little movie the 4 of us made the night before They eagerly said okay!
I knew immediately things was about to start up again and that was fine by me. What tipped me off first was the seating arrangement. Candy, Jo Ann, and Sherry were seated on the front row, and me in the center on the second row with Steve to my left and Ken to my right. The movie hadn't been playing for 3 minutes when I felt a hand coming from my left inching it's way up my tiny little skirt. I opened my legs to give him a little better access. About the time I did that I felt another hand coming from the other direction going up under my top. About the time the hand under my top slipped my bra up exposing my bare titties Steve whispered in a very low voice, Aren't you the little whore? Inviting guests over to see you get your gurl pussy pounded and your mouth filled with cock! Then Ken said to Steve, Do you think we need to punish the little whore? Maybe she needs to be put on the wheel or maybe even put in the stock and then see how she likes the fucking machine. Steve said, yeah, that's a great idea, she can even take turns sucking us off as she takes that big dildo. All 3 of the girls are bisexual and they had their own thing going on the front row, but I couldn't concentrate on them for Ken and Steve. One of them, I am not 100% sure which finally got his hand positioned in such a way as to get a finger in my gurl pussy and that was all it took to send me over the edge and I lost all track of time.
The next thing I knew the movie was over and Ken grabbed me by the arm and said, Okay Slut, let's go. The big wheel was sitting on a spot where there looked to be a drain in the floor right underneath it. Steve had me step up on the two pedestals at the bottom of the wheel, but not before he told me to strip to my bra and panties. I am a very submissive gurl and find it near impossible to disobey a command from anyone. He strapped my ankles tightly to the wheel. This made my legs spread open wide. Ken took my left arm and strapped it and then did my right. This positioned my arms wide and above my head. This wheel was mounted on bearings so it spun easily and would turn on its own for a long time. The last strap Ken added went around my waist. Ken had no more than got the last strap buckled when Steve reached up high on the wheel and gave it a nice hard spin. It seems as though I was strapped to a car tire and the car running 55 mph! By this time both Steve and Ken had dropped their pants and underwear and had their cock in hand. About the time I thought what are they going to do, two streams of water began hitting me! Oh, My goodness, they are pissing on me. By the time they finished, I had piss in my mouth, my ears, and even up my nose. Steve stepped on a pedal to the left side of the wheel and it began slowing down, and finally came to a stop with me upside down. Ken turned the wheel so I was back right side up and began unbuckling the straps. I was drenched in piss and so dizzy I couldn't even stand without assistance from both Steve and Ken.
Ken looked at Steve with an evil smile and said, should we give her a taste of the machine? Steven and Ken walked me over to this thing that looked like a small table and at the end, it had cutouts for my neck, and wrists and when I placed my neck and wrists in the cutouts, with their assistance there was another part with matching cutouts that came down and latched so it was impossible for me to get my head or arms free. Once in this position, I could only see things directly in front of me but felt someone grab my panties and pull them down to my ankles. Next, I felt a hand on my ass and near my gurl pussy, then felt something cold on my pussy, and then what felt like two fingers enter me. I then felt something cold touch my pussy for a few seconds then push its way inside me. By this time both Steve and Ken were only semi dressed, neither had anything on from the waist down. Steve was nicely hung with around 7 inches but Ken had closer to 9 or 10. I assumed whatever I felt enter my pussy was the machine they were talking about as it began to pump my tight hole. It pumped me very slowly at first but after a time began to gradually gain speed. Ken walked around in front of me and put that big thing near my mouth. I struggled to reach it but couldn't quite get it in my mouth. Finally, he gave it to me and I sucked him as the machine pumped my horny hole. It didn't take too long before I could tell Ken was on the edge of cumming. I was so excited thinking he was going to fill my mouth with his jizz, but just about then he pulled his cock from my mouth and filled my face full. Just a few moments later Steve stepped in front of me and his cock looked rock hard too. I sucked him off as well and got another splash in my face for my efforts. The fucking machine they were using on me dispensed lube ever so often and kept my pussy nice and lubed but it had been going for a time now and my little hole was beginning to get sore when Steve stopped the machine and pulled the dildo out of me.
While all this had been taking place the 3 girls had their own fun, fucking sucking and eating each other. Jo Ann came over to me and said, why don't you and Candy call it a night, you have a lot to do tomorrow to get things all squared away in your new house. I will give you something to look forward to though. Be back here tomorrow night at 6 PM sharp, we have a big surprise for the two of you that we are sure you will love! We said our goodbyes and headed back to our house. I am not sure if any of our new neighbors were watching but I am quite sure I was walking a little bit funny after the pounding my gurl pussy took from the machine and both the guys.
The next morning came too quickly but we got up and began our task of getting the
the house in order. About 4 Candy said let's call it a day, and get ready to go over to Steve and Sherry's. I am just dying to find out what kind of surprise they have for us. Sherry took her shower and while she was getting dressed I took mine. I sometimes still needed a little help with my makeup to make it look like I want it to look, and that way she was able to help me. We opted to wear some Hooters style shorts and a purple top. My shorts were white and had SLUT written across the ass and Candy's was black and had Bitch written on them. Since our shorts were rather risque, we decided to go out our back door and go a couple of hundred feet over to their house since that area wasn't as well lit. We rang the bell and this time Jo Ann answered the door and said, come in girls we have been waiting for you! As we started down the stairs to the playroom Jo Ann said, I know your pussy took an awful pounding last night, I hope it isn't too sore for some fun tonight as she grabbed a big handful of my left ass cheek. I replied, Of course, I am ready for some more fun
When we got to the bottom of the stairs I was aghast! Every seat in their theater, all 24 of them were filled and what's more, they were watching me get my pussy drilled by that machine. I could tell that they had seen everything that transpired the night before and were very near the part where we decided to call it a night. Within two or three minutes the movie ended and everyone got up and came over to us and seemed anxious to meet the star of the movie they just watched. None of the men had on anything more than very skimpy underwear and a couple was completely naked. None of the women had on more than a pair of G sting panties or a thong. Jo Ann said, Why don't you two take off your top and shorts, get comfortable and I will introduce you to everyone. Jo Ann introduced us, one couple at a time, and told me they were all members of The Bottoms Up Sex Club of GreaterChicago and all of them lived within a block or two of our house.
Now I had already had one shock when I came down the stairs and saw all those people but by far the biggest one was yet to come. Candy looked at me and said, Come over here sweetheart, we need to talk. I followed her to a table and she began by saying, As you know I grew up here and lived here up until shortly before you and I met. My mom and dad were co-founders of Bottoms Up. When we met, I thought I could give all this up but found it wasn't possible for me to do that. She then confessed to giving me estrogen instead of the testosterone I thought I was taking. I have known most of, these people since we were all k**s, and I knew in advance everything that has happened. That said, you have every right to leave me and never look back but I am hoping you don't. I was fighting mad for a few moments but then it hit me, why should I be angry? I have had the time of my life since all this started and told her so, and that I was okay with it all, just wished she had gone about it a bit differently. Once Candy raised her hand with the thumbs-up sign everyone let out a cheer that I am sure the whole neighborhood had to hear.!
Sherry came over and said, now that everything is out in the open, are you ready for your initiation ceremony to become a full member of Bottoms Up? Thinking I had come way too far to turn back now, I said yes. Sherry said, Well then, I'll let Miss Jo Ann explain everything to you.
Okay Desiree, let me first say every woman in this room has been through this process at one time or another, and yes, that includes your wife. Do you see the door over behind the staircase? In that room is a photo of each and every girl here except you taken just seconds after this process is complete. Yours will soon be there as well. Now I'll try to explain the process. All the male members will form a line. This is one reason I had you to take off your top and shorts. The first man in line will walk up to you and begin jacking his cock. As he stokes he will tell you where he wants to shoot his load, and what position he needs you in to do it. He is free to select any part of your body he wants as his target, ass, titties, face or where ever he chooses. You will do your best to get in the position he wants and then he shoots his cum where ever he stated he wanted to. Then the next man in line does likewise and this continues until you reach the end of the line. Once the end of the line is reached, Ken or I will come and take a photo of the cum drenched Desiree and we will frame it and it will assume it's it's rightful place alongside all the other girls. Do you understand all this? Do you have any questions?
I said I do understand, but I also have a question. Let's just say I was entering the club as a man, is there an initiation? Jo Ann looks over at Ken and says, You want to take this one? Ken says sure. Yes, there is an initiation for men too, and every man here has been through it just as the ladies have been through theirs. It goes like this. There is a hat in the room Jo Ann showed you earlier. Under it is strips of paper, each one identical to the other in every way. Each female here will write her name on a strip of paper then fold it in half three times and drop it in the hat. Once all the girls have their name in the hat, the male inductee draws one strip of paper and reads the name aloud, then strips completely naked. The inductee is then seated in the room and the door is closed. Whichever girl is selected by the name draw will then approach the room with a digital camera. She then opens the door, enters, and closes it behind her. She can then do anything she wants to make his cock hard, but can't touch him. At the end of ten minutes, a timer sounds and, she snaps a photo of the guy's cock. Now for the fun part. The photo is then judged by all the other members male and female and a vote is taken as to whether she made him sufficiently hard or not. If she fails to make his cock hard the guy is accepted and no further action is taken, but if she succeeds, the guy must then draw one more name from the hat. That girl approaches and has the inductee to bend over and grab his ankles. She is then given a leather belt and is instructed to strike his bare ass with the belt 5 times and do it as hard as she likes. There is one footnote to this, so far, no man here as made it without getting a smack on the ass with the belt.
My initiation went off smoothly, but I was a mess when they finished. There were 14 men total and 7 chose to cum on my face, 4 chose to cum on my titties, and 3 wanted to cum on my ass. When you enter the room and look at the back wall, my photo is 3rd from the left.
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