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It is every crossdresser's dream to find a girlfriend who is really into helping him and sharing with him the joy of being a girl. I was lucky enough to find just such a girl. We had only been dating for about a month when we decided to live together. And it was only about another month before I opened up to her about my love of wearing beautiful lingerie and dresses, and using make-up and wigs to complete my look. Her reaction to my revelation surprised and delighted me.
"You mean you enjoy wearing a bra and panties?" Said my girlfriend Valerie.
"I do, but I don't stop there. I really enjoy adding a slip over my bra and panties plus a sexy garter belt and nylon stockings and wearing a pretty dress. Then I have learned how to apply make-up and a wig and the end result is I am completely feminized. It turns me on." I said directly.
"So is that why you have no body hair to speak of?" She asked.
"Yes, I shave myself on a regular basis." I replied.
"When you are dressed as a girl, do you have a female name?"
"Yes, it's Julie."
"That's a pretty name. And you may find this surprising, but I think it's kinda sexy. I like how kinky it is and I'm thinking of the fun I could have with you fully dressed." Said Valerie.
"You have no idea how happy I am to hear you say that. I really love hearing you say it." Was all I could say.
That night I pulled out my extensive wardrobe of vintage lingerie, dresses, make-up, and several wigs. Valerie loved my taste in women's clothing. Over the next several weeks together she assisted me when I dressed and she wanted me to fuck her when I was in my wedding night lingerie. I tried to do this on more than one occasion but was never able to get my smaller than normal penis hard enough to really turn her on. Each time I had to pull my half-hard erection out of her and hand stroke myself for several minutes before I managed a very weak ejaculation. When I was fully into girl mode, trying to have intercourse as a male was basically impossible.
The solution we came up with was to have me eat out her pussy and use my tongue on her clit to bring her to orgasm. I became very good at it and every time I pulled down her panties to do this her pussy lips were very wet and very swollen. After she climaxed from me sucking on her clit I would then suck on her large, erect nipples while I slid my fingers up inside her cunt. It did not take long for her to gently slide my face back between her legs where I again sucked on her clit giving her a second full orgasm. We had sex with me on top of her like this and then we had me lie on my back and she would sit on my face and grind her wet pussy into my waiting tongue and lips. She enjoyed the idea of another girl having sex with her even if the other girl had a penis. From this point forward we never engaged in sex unless I was fully dressed as a girl.
"I think I'd like it going forward if we stopped trying to have male/female intercourse. I've been reading and thinking about this, and when we have sex together I want you to be in full girl mode. I also think we should explore locking up your little penis in a male chastity cage before I let you eat me out." Smiled Valerie.
"If that's what you want, I'll do it. I have about four different chastity cages already and I'd love to have you help lock me up." I smiled.
"Look at you, you sexy thing." Smiled Valerie.
I got out my smallest cage and Valerie lubed up my ball sack and pulled my little balls through the metal ring. The ultra-small cage on the front held my little penis head tightly as she locked the device and held on to the key.
"Oh yes. You are really my little sissy now aren't you? Not only do I want you to look feminine, I want you to act feminine." Smiled Valerie as she leaned in to kiss me.
"I am your sissy, and I love being your sissy. I will do anything you tell me to do because I love being a girl with you." I replied.
"Oh good, that's what I wanted to hear. Now that you are locked and caged, if you start to have an erection it will really be painful and your body should get the message in no time that erections are something a girl like you should just not have." Said Valerie.
"I know you are aware that my erections before were not very hard." I said softly.
"No they were not, and now, you won't be having any at all unless I let you. I'm going to leave you locked and caged for a very long time. During that time I want you to control any sort of ejaculation you may feel the need to have. You are a sissy girl now and girls do not ejaculate, so promise me now you will stop any sort of ejaculation you feel coming on. Locked down as tight as you are should help you a lot, but I know you can control things to the point that you can stop ejaculating since I told you to." Directed Valerie.
"My ejaculations are messy and dirty and as a girl I really hate it when they happen. I now have a reason to stop them and I will. I will not ejaculate from this day forward." I assured her.
"Good. As long as you are going to do as I say, I'll take over paying the bills. I want you to quit your job and live here full-time as my sissy girl. Bra, panties, a slip, garter belt and stockings under your dress every day. Make-up is a must. I'll allow a wig for now, but you're going to grow your hair out until we can get you a feminine hairdo." Directed Valerie.
I was so deeply into being a girl, and I did present myself as a very pretty girl, I could not say no to Valerie's direction. All of my remaining male clothing was disposed of. My lingerie collection was now into our bedroom dresser and my dresses lined up in the closet. Before I realized it, six months had passed and not once during that time had my chastity cage been unlocked. I was actually proud of the fact I had not ejaculated. My hair had grown to almost half-way to my shoulders but I still looked better wearing a wig. Valerie was still directing me to perform oral sex on her and I did it every time she asked. My tightly locked chastity cage prevented any sort of erection feelings, and my body was being trained to feel an erection as something painful and something to be avoided.
I didn't want to tell Valerie that after more than six months of sucking her clit and sticking my tongue into her pussy followed by sucking her nipples, I was beginning to feel this sexual activity was more a chore than it was a pleasure. It was around this time that Valerie came home with a few sex toys and things became interesting again.
The first toy she showed me was a set of four butt plugs in various sizes from smaller to larger.
"I've read where sissy's wear butt plugs on a more than regular basis. Some of their girlfriends have their sissy wear the plug all day. I'm going to start you with the smallest plug and then I'm going to over time graduate you to larger and larger plugs. In the beginning I'll only have you insert the plug when we have sex. Later we'll see if I want you to wear it for an extended period of time. Although, I must say, you have been a very good girl wearing your chastity cage for as long as you have. You haven't ejaculated when you were with me, have you ejaculated at all since I locked you up?" Asked Valerie.
"Oh no! Not at all! I'm a girl; you know I'm a girl and girls don't ejaculate. Before you locked me up I told you how much I hated ejaculating. The cage prevents me from getting hard or even plump so ejaculation is out of the question. I never have even a hint of semen in my panties. I know, because I check every night." I said with conviction.
"That's my good little sissy. I knew I could depend on you." Said Valerie.
The second sex toy she produced was a dildo molded in the shape of a thick male erection, complete with raised veins and looking very realistic.
"Since we don't have intercourse, I'm going to fulfill my need for a real man's cock with this dildo and I'm going to insist you watch when I use it so you can learn how a woman has an orgasm when a man is fucking her." Said Valerie.
"I always do as you ask." I replied.
"Good. Because I want you to put your face in my pussy, but first, I want to start you on the smallest butt plug and I want it to stay inside you the entire time you are giving me oral sex. Now be my good sissy and lift up your dress and your slip and pull down your panties so I can insert your plug." Smiled Valerie.
I got on the bed on my hands and knees and lifted my dress over my waist, then I pulled my full slip up above my waist and then pulled my full-cut panties down to my knees exposing my hairless butt and genitals. Valerie took control from this point and put a large amount of lube on the plug and spread a little on my hole.
"Okay Julie honey, take a deep breath; I'm going to slide the butt plug up inside you. Let me know if I'm hurting you. I'm going to go real slow and I have read if you totally relax it will make the insertion much easier." Said Valerie as she slowly pushed the pointed end into me.
I did everything I could to relax back there and I took in a breath and to my surprise the butt plug slid up inside me without pain and very effortlessly.
"There, it's all the way in. How does it feel?" Asked Valerie.
"It actually feels really good. I'm surprised how easy it was. I can probably take bigger plugs in the future without much problem." I replied.
"Oh that's good to hear. I hadn't looked at your locked cage in a couple of months, but seeing it now it looks like your little ball sack is a very deep red color, almost purple. I've had you locked for over six months and I know you sit down to pee. Do you think the cage is doing serious damage to your balls?" Asked Valerie.
"You know what? If I'm being honest, I really don't care if it is. Valerie honey, I've gone past just being a sissy. I am mentally very deep into being a girl. And the girl in me actually wants to damage her little balls and penis. I would like nothing better than to have my balls stop pumping testosterone into me. I have a mostly numb feeling between my legs now after being locked up so long. I fairly sure I have lost the ability to have an erection. If my little balls shrivel up and stop working I would be a very happy girl." I replied.
"Okay then, I hear you. Pull up your panties tightly to keep the butt plug in and pull your slip and dress back down. I'm going to strip completely nude and I want you fully dressed as you suck my clit and tongue my pussy." Said Valerie as she took off all her clothes in front of me.
My full cut panties kept the butt plug snugly in place as I began my task of sucking on Valerie's clit and licking her wet pussy. Her pussy lips seemed extra-large and wet as I did what I normally did for her. Also, her nipples seemed extra-large as she was breathing deeply. All of a sudden Valerie began talking dirty about us as I keep pulling on her clit with my lips.
"Oh my God Julie! I find it so hot that I have kept you locked up tight and I might be destroying your little dick and balls! I love it when you suck on my clit, and I really love it that it's impossible for you to fuck me. Only a real man can fuck me and you are most definitely a woman. Keep pulling on my clit, I can feel it getting longer. I'm really horny tonight baby."
I took a break from sucking on her to answer;
"You're right, I'm really a girl. I'm not a man and I'm not a sissy, I'm a girl. It's impossible for me to ejaculate and my little dick is the size of a clit. I look and act like a girl all the time and I love it. I want to stay locked as long as I can and I never want to fuck another woman, ever."
"That's what I want to hear my good little girl, now suck on my nipples and then finish me off on my clit." Gasped Valerie.
I sucked each of Valerie's bulging, erect nipples and I fingered her soaking wet pussy. She delicately pushed my face off her chest and onto her cunt. Her pussy lips were fully engorged and swollen open to the point I could see into her vagina. As a man I would have wanted to fuck her deeply, but as a girl I had no desire to do this at all. Instead I sucked on her rock hard clit that had stuck up so big, it looked like the tiny head of a penis. I put my lips tightly around her wet clit and sucked as hard as I could and Valerie's body began to shake violently as she was not in control of her orgasm.
"Oh fuck yes! Fuck yes! I'm being fucked by a girl and I'm cumming so hard I almost can't breathe!" Shouted Valerie as love juice poured out of her pussy and onto my face.
As Valerie orgasmed a second time and more violently than the first, I was very proud of the fact my tightly locked down genitals had no movement in them at all. No trace of a wet ejaculation and no attempt at plumpness. I was a girl between my legs and had worked very long to be one. I did however begin to notice a sensation I never had before with the butt plug firmly inserted inside me. My panties held it in tightly and without any ability to control it, I suddenly felt what I later found was an anal orgasm. My butt lips clinched and released the plug several times and I had a very pleasing sensation in my rear. I had cum with most of the sensation internally. I was really, really experiencing sex as a girl and it was wonderful.
It had been over ten months of me living full-time as a girl and there was no chance or way I was going back now. My hair had been growing and was just touching my shoulders and was long enough to have a pretty, feminine hair-do. I had graduated slowly to the largest butt plug Valerie had for me and I liked the sensation so much I found myself begging for her to insert it into me. She always inserted the plug before I did my duty of oral sex with her, and then once, I was able to leave it in all day which I found very erotic and very pleasing.
As the one year mark approached of me living as a girl I got the courage to ask Valerie if she would help me.
"Valerie honey, don't take this the wrong way, but I would like it if you would help me find a man who would like a girl like me, you know, a Daddy. I'm a girl and I would like to have a man take care of me, love me, and make love to me. And I would like to do the same to him." I said with conviction.
"I knew this was just a matter of time Julie. You are such a pretty girl. There is nothing at all about you that is male except for your tiny locked up penis and ball sack. I know you haven't ejaculated in almost a year now, and I'm not sure you ever will." Said Valerie.
"I really don't want to ejaculate! I just hate the idea of doing it." I said quickly.
"I know honey. I think I have a way for me to assist in finding you a Daddy. I've seen dating websites for girls like you and some of them are specifically for girls looking for Daddies. Why don't we post some of your pretty photos and build a profile for you and see who responds. I'll go with you for your first meetings and we'll see what you like. I'm sure men will love to be your Daddy." Smiled Valerie.
It only took less than a week before I had responses from several different men interested in my profile and photos. With the help of Valerie we narrowed the list down to a man named Ron who lived fairly close to our place. We arraigned to meet Ron at a bar that was open to girls like me and Valerie went with me on my first "date."
When Ron came up to us at the bar, I was shocked at my internal reaction to how handsome he was. I was still tightly locked between my legs, but I felt my nipples immediately rise to attention in my bra. I'm sure my eyes dilated too as I saw him in person for the first time. I was praying to myself that Ron was a good and decent man, and in just a few moments, my prayers were answered.
"Hi, I'm Ron, you must be Julie, and you must be Valerie." He said in a smooth voice.
"It's so nice to meet you Ron, I'm Valerie and I can tell from Julie's reactions she is very happy to meet you too."
"Hello Ron. You look just as you described yourself in your photos, and I must confess, you are very handsome." I said in a soft voice, extending my hand that Ron gently kissed.
The three of us spent a little over two hours talking and getting to know one another when I felt Valerie touch my leg under the table letting me know that she approved of Ron. I had approved of him ten minutes into our conversation, and in a bold move, we invited Ron back to our place for the evening.
When the three of us got home we all knew what was about to happen. I had worn a very feminine knee length white dress that was covered in lace. I had on a six strap garter belt holding up my white nylon stockings. I had intentionally put my garter belt on first and then pulled up my full-cut panties so if things became sexual I would not need to take off my garter belt to pull down my panties. All of my lingerie was a virginal white with lots of lace.
"Would you like to follow us to the bedroom for some intimate fun?" Asked Valerie.
"If you two would, I'd be happy to." Replied Ron.
"Julie has asked me to stay in the room with the two of you if that's alright." Said Valerie.
"I'm up for whatever makes you comfortable." Said Ron.
I could see the front of Ron's pants and he was indeed "up." He was sporting a fairly healthy erection pushing his pants forward.
"Ron, I don't want to lie to you, I am a complete virgin at this, but I am really attracted to you and I'm hoping you feel the same toward me." I said in a shaky voice.
"Julie honey, you are more beautiful in person than your photos and I am really turned on by you." Replied Ron.
"Why don't you take off all your clothes Ron and I'll help you get Julie ready." Said Valerie.
Ron shed his clothes so quickly it was startling, but not as startling as the size and shape of his erection. His cock was perfectly straight and was so hard it looked as if it was straining to become bigger. I found it to be a perfect length, and to my relief it wasn't overly thick. It was just as hard as a rock.
"Julie sweetheart, why don't you lift up your dress over your waist and then lay back on the bed." Asked Valerie.
I did as she asked and Ron's cock wiggled when he saw my full-cut nylon and lace panties with lace all across my butt.
"Now Ron, Julie has been locked tightly between her legs for almost a year now. We think the locking cage has atrophied her tiny genitals, but tonight, I'm going to give you the key to unlock her. We're fairly sure she will have no sexually physical responses down there. I'd like you to pull down her panties and I'll get the key to the lock." Said Valerie as Ron did as she asked.
With me on the bed on my back and Ron between my legs he gently pulled at my panties and slid them completely off. When he saw this he leaned over and lowered his face to mine to kiss me and I willingly accepted his lips and his tongue into my mouth.
"Here's Julie's key. It's the first time she's been out of her cage in almost a year so be gentle." Said Valerie.
Ron unlocked my cage and slowly pushed my always numb ball sack through the ring and I was totally free, but nothing at all happened, much to my relief. The cage had immobilized my dick and balls for so long that they did not at all move when unlocked.
"Do you have any cotton love ropes?" Asked Ron.
"We do. What do you have in mind?" Asked Valerie.
"Nothing intense. I'd just like to tie Julie's wrists to her ankles so it will be easier on her and on me when I push her legs back up." Said Ron smiling.
Valerie returned with some pink cotton rope we had used before and my wrists were gently, but tightly tied to my ankles. And thankfully my little dick and balls remained lifeless.
"Your erection is beautiful Ron, but please remember, I'm a virgin with a man." I said sweetly.
"I know honey and I'll go slow. Just let me know if I'm hurting you in any way." Replied Ron.
We did not tell Ron I had been stretched several times with a butt plug and we allowed him to put as much lube as he wanted on his erection. Ron gently pushed my legs back up over my head forcing my arms with them and I knew that my hole was fully exposed to his erection. With that, Ron pushed himself forward and playfully slid the helmet of his cock up and down my waiting hole and then I felt the head of his manly cock begin to enter me.
"Oh my God!" I gasped.
"Am I hurting you?" Replied Ron quickly.
"Not at all! You have no idea how long I've wanted to do this! Keep pushing, all the way inside. Fuck me Ron! Fuck me till you cum!" I said breathlessly.
Ron did as I asked pushing in and out of me and I clinched my butt lips around his rock hard cock.
"Julie baby, you are so tight around my cock, it feels wonderful!" Gasped Ron.
I felt Ron's pubic hair touch against my bottom and I knew he was fully inside of me. I was still wearing my white lace dress and bra and slip and garter belt with my stockings. Everything but my stockings was pulled up over my waist. Ron then began to turn me over on my side and then on my stomach with my butt sticking up in the air. My wrists were still tied to my ankles as he again entered me from behind as deep as he had when I was on my back.
"Oh God Ron! It feels so good! You're fucking me so good! Please don't pull out! Please cum inside me! I want your sperm inside me! Oh fuck! I'm a girl!" I shouted as I felt Ron's cock swell quickly followed by hot shots of semen. He was ejaculating inside of me just as I had hoped he would. My lifeless cock had not moved and showed no signs of anything coming out of it, but my ass began to squeeze and shake around Ron's exploding cock and I experienced an anal orgasm. I had never had sex so intense and so physical. I was in heaven; in girl heaven, as I had managed to excite a man to ejaculate inside my body.
Valerie stood silent next to the bed as she watched Ron fuck me. She could tell my sexual encounter was over the top pleasing to me. As Ron's cock softened he let it naturally slide out of me. Then both Ron and Valerie untied my wrists from my ankles and Ron, still fully nude leaned into me and gave me a long, deep tongue kiss on the mouth. My little penis and ball sack still fully limp for which I was very proud.
As Ron and I lay on the bed catching our breath, Valerie handed me my panties and I pulled them on happy in the knowledge I had a real man's semen and sperm deep inside my body. Ron again kissed me and got up and got dressed and told us he would call me in the morning.
After Ron left and Valerie had shown him to the door she came back into the bedroom and quickly stripped herself totally nude. She climbed on the bed and straddled her soaking wet pussy over my face and lowered herself to my mouth for me to suck on her which I did. I put my lips around her hard clit and pulled gently as she started to cum. My lifeless cock and balls remained soft in my panties even though they had been unlocked for the first time in almost a year. It was fairly obvious to me I had damaged my male sexual responses with the lengthy caging and I could not have been happier. Valerie came very quickly and then rolled over next to me on the bed.
"It looked like you really enjoyed losing your virginity to Ron tonight." Smiled Valerie.
"I sure did. It was much easier than I thought, and the feeling was much more enjoyable than I thought. And I was really taken by how handsome I thought Ron was. He was so good looking it really turned me on. I find it exciting that I get turned on by men. I'm really enjoying life as a girl." I replied.
"Ron seemed to be very gentle with you when he first entered you, then he became more physical as he plunged deeper and faster and then he seemed to really have a strong orgasm." Said Valerie.
"Oh he did. I really hope he enjoyed it. He gave me an anal orgasm as I really enjoyed it. I hope he calls us again and wants to take me to bed again. I'm feeling very lucky that we found such a nice and caring man with him." I smiled.
"You mean you could see yourself in a long-term relationship with him?" Asked Valerie.
"The sexual glow of him is still with me at this moment, but yeah, I could see myself as his live-in girl, and maybe even his wife." I said with surprise.
I was very pleased that Ron did call us back the next day and we scheduled another evening together at our place the next night. This time I was on my knees in front of him and willingly took his erection into my mouth. I loved the feel of his hard cock and the taste of his pre-cum. I was the one who provided the lube with my mouth before he had me on my back again with my panties off and legs over my head as he fucked me with Valerie watching everything. This time Ron pulled on my limp little penis as he penetrated me and there was no sexual response at all. He only needed two fingers to pull on my lifeless little cock and no semen came out, not even pre-cum and no hint of any plumpness or hardness. I was truly a girl when it came to sex. It had only been a couple of days but Ron shot a huge load of semen and sperm deep inside me and it was more than wonderful.
"Oh my God, Julie! You are so feminine! I'm in love with fucking you." Gasped Ron as he came.
"I'm a girl Ron. I'm your girl and you are my man. Do you want me as your girl?" I asked in a coy voice.
"Julie honey, enjoying sex with you is wonderful. I've never had such an emotionally intense experience as I have had with you. I just want to understand what you are asking." Said Ron as he was still naked and getting soft.
"If you would allow me, I think I can speak for Julie and fill you in on what Julie is asking." Said Valerie.
"Thank you Valerie, I would really appreciate that." I said as I pulled my panties back on again filled with joy and Ron's semen.
"Julie has asked me to help her find a 'Daddy' who would accept her for who she is. She is looking for a man to love her and she in return wants to give her love to that man. We've been talking about it and we believe we have found that man with you Ron." Said Valerie.
"Go on, I'm listening, because I believe we are both wanting the same thing." Said Ron.
"Julie and I have lived together for well over a year now. She has lived as a girl almost all of that time. She is not capable of any sexual act as a male, she is only sexually active as the girl you see she has become. She wants you Ron, if you would be willing to have her as your girl," Continued Valerie.
"Is that true Julie?" Asked Ron.
"It's more than true Ron." I replied.
"Would I need to lock your little genitals into chastity again?" Asked Ron.
"I will do anything you want honey. I want to be your girl and I want to please you, but just so you know, I haven't ejaculated in almost a year and a half. I haven't had any form of an erection in that time too. I'm convinced my male sexual response days are well behind me and the only sexual responses I am capable of having are female. And I want to be your female partner if you will have me." I said in an emotional way.
"So you're sure about this?" Said Ron.
"Ron baby, I love you and I want to live with you full-time as your girl. I want to do what makes you happy, because that is what will make me happy. And I want our sex life to be full. I love tongue kissing you and hugging you too." I said smiling.
"I have to admit, I have never had such intense orgasms as I have had with you baby. And I love that your penis is so tiny. If it ever starts to get bigger you'll let me lock it down tight won't you?" Asked Ron.
"You can lock me up any time you want honey. But I'm pretty sure you won't have to I'm deeply, deeply, into being a girl and I have no use for a my penis. But I love having a use for your penis." I smiled.
"Okay then. You found me on a site that said I wanted a partner, and I want you as my partner. I'm really taken with your femininity and I had no idea I would find a partner as feminine as you Julie. I know we can make a good pairing and an ever better couple." Smiled Ron as he leaned in to kiss me.
"And if things go well for us, I would like you to know, it would be a very happy and sexy day for me to be able to wear a beautiful satin and lace wedding gown and become your bride." I said returning Ron's kiss.
"We'll take things one step at a time and I'm sure things will work out the way we want them to." Replied Ron.
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