Sissy Date Turns Serious

Sissy Cindy had been a sissy for as long as she could remember. In her middle twenties she began looking for dates with men who liked having sex with a girl like her. Even though she was physically in her prime as a male sexually, she had no interest at all in having sexual experiences with biological females. She had a very tiny "clitty" between her legs and it rarely, if ever, expelled anything close to what could be called semen. At 25 years old she had ejaculated only once and found she was not a fan of the tiny mess it made.

Cindy was a very feminine and very pretty sissy. She wore only the most feminine lingerie she could find on a daily basis. She had a pair of full size 38C silicone external breast forms that filled out her figure in a most natural female way. When she began posting profiles on sissy websites looking for men who wanted to date her she had more than enough offers.

To screen her potential male dates she would develop a rather lengthy email correspondence with the men and after about three months or so, if she felt comfortable with the man, she would consent to going out on a date. Following this type of procedure she had never had any kind of a problem with a man at all. In fact, most of the men she dated were kind and very caring.

When Cindy prepared for a date she always spent several hours making sure her make-up, hair, finger and toe nails, lingerie, and dress were just right and put her in the best light as the real girl she was. All of the men she dated were always taken aback by how pretty she was and they all told her so. Passing in public as the pretty female date of a handsome man was never a problem at all.

Cindy had a few second dates with a handful of men, but it was her date named Jack that really excited her. When Jack asked her out she was always more than willing to go. Jack was a nursing assistant at a local hospital and he was every bit the total gentleman. Cindy and Jack had communicated by email for several months before their first date and she felt they really had a strong bond. She felt she could tell Jack anything and he would understand. They had shared well over two dozen dates that all finished with the two of them in bed making gentle and passionate love.

During their email correspondence and in bed sharing "pillow talk," Cindy had more than once shared with Jack her disappointment that she had to deal with the little mound and two testicles she had below her "clitty." Jack had always told her he did not mind and found how tiny they were to be a real turn on for him.

Cindy and Jack always met each other at a nice hotel room that Jack always rented. As the two of them had sex together on a more and more regular basis they began to push the bounds of sexual activity. Cindy allowed Jack to slowly insert a small butt plug into her and she also allowed Jack to tie her up sometimes before he lowered his manly erect cock into her mouth for her to suck him to orgasm. Cindy could not get enough of swallowing semen from her male lover. She loved the feel and taste of Jack's ejaculate.

It was the consensual pushing of sex play boundaries that led Jack to do something to Cindy that would change her life forever. Everything started as their dates always did, meeting in a nice hotel room. Cindy was in bed with Jack in her long pink nylon and lace nightgown as she kissed, licked, and sucked on his long thick cock. She was soon rewarded with an extra heavy load of semen and sperm that shot into her mouth as Jack gasped and came. Cindy took her time swallowing Jack's load and then the two of them cuddled together in bed.

"Jack honey...That's the biggest load of semen I've ever seen you ejaculate. You must have been extra turned on today." Said Cindy.

"I am sweetheart. I have been thinking about enjoying a little extended sex play and it really has me excited." Replied Jack.

"Ohhhh, that sounds like fun. What would you like me to do?" Said Cindy in an excited way.

"I think it would be fun for us to play a little tie up game and then I want to give you something you have told me you have always wanted." Said Jack.

"I'm all in. What do you want to do first?" Asked Cindy.

"Well first I would like to tie your wrists to the headboard spread eagle."

Still nude with his manly cock now fully limp, but still long, Jack got up from the bed and went to a bag to get some cotton rope. Cindy still had her nightgown, panties, and bra on as she watched her handsome man come back to the bed. She raised her hands over her head and Jack used slip knots on her wrists and he tied her to the headboard. The knots were tied so as she pulled on them they only became tighter. Jack teased her a little as he allowed his limp cock to dangle in front of her mouth as he adjusted the ropes.

"I'd like to try something new honey...I like to put a ball gag on you, but it's the kind with holes in the ball so you can breathe heavily if you need to." Said Jack as he again went to his bag.

Cindy was silent as Jack put the ball in her mouth and gently lifted her head off the bed to tie the gag firmly in place.

"Are you okay honey?" Asked Jack.

Cindy could only grunt as she nodded her head that she was fine. Jack then again went to his bag and came back with a butt plug that was about twice the size of any he had ever inserted into Cindy before. Cindy's eyes grew wide as Jack showed her the plug as he put some lube on the tip of the plug. Jack then lifted Cindy's long nightgown up to her waist exposing her heavily lacy full cut panties. Slowly he pulled her panties off her legs exposing her tiny clitty that was extra small as she began to become a little nervous. Jack gently pushed her legs apart and looking her straight in the eyes he began to ease the butt plug inside of her. The feeling made Cindy gasp at first and then she relaxed as the entire length of the plug eased inside her body.

"I knew if you relaxed you could take that." Said Jack. Cindy just nodded her head in agreement.

"One more new thing for me honey..." Jack said as he went to his bag and came back with a black full head covering.

"This will be better for you if you are not able to see for a few minutes." Said Jack as he quickly pulled the black nylon hood completely over Cindy's head. She could not see a thing and she began to thrash her still untied legs around as she grunted through her ball gag.

"No...No...honey. You are just fine...No need to thrash, everything is okay." Said Jack quietly.

Cindy's nightgown was still pulled up in front exposing her nakedness from the waist down. Her butt plug was firmly inside of her and her tiny clitty was getting even smaller. She could hear Jack going over to his bag and when he returned he began to fondle the tiny mound under her clitty. He was feeling around for her testicles and when he could feel them he was gently pulling them down to put some space between her ball sack and her body.

"This is something you have always told me you wanted. You want your testicles to stop working so you can become a complete woman. I've got the stretchy kind of rubber they pull tight around your arm when you have a blood test and I'm going to stretch it tight on top of your little ball sack. It should come close to stopping the blood flow to your little balls and they will stop working and dissolve in your body." Whispered Jack.

Cindy began to thrash some more but Jack held her down and she could feel the thick rubber band being wrapped between her legs. It was very tight and she felt a little pain almost immediately.

"There we go...All done. It will be difficult for blood to get through that." Said Jack as Cindy was huffing and puffing through her ball gag inside her hood. Jack removed Cindy's hood as she looked a little scared.

"Don't be scared honey. This is what you have wanted. I have a shot to give you that will dull any pain, but it shouldn't be long before that area goes numb and you won't feel anything." Smiled Jack.

Jack gave Cindy an injection in her naked butt cheek of what he told her was a pain killer, but it was really her first shot of testosterone blocker. Next, Jack showed Cindy a full size female pull-on diaper. He put her legs into the diaper and pulled it up all the way. This was followed by him putting her lacy panties back on and pulling them up fully and then he pulled her long nightgown down all the way to cover her up.

"You want to be a girl don't you?" Asked Jack.

Cindy nodded yes. With her nightgown pulled down Jack then proceeded to tie each of Cindy's ankles spread eagle to the bed. Loop knots were again used and the more she pulled against the ropes the tighter they became. Cindy was completely spread eagle on her back and tied tightly to the bed. Jack then leaned over her and began to untie the ball gag. He was about to add another bit of fun to the moment.

"I'm going to take off the ball gag just for a little bit as I want you to drink some water." Said Jack.

"How much?" Asked Cindy.

"I'm going to help you drink an entire pitcher of it." Replied Jack.

"Why so much? It's going to make me pee." Said Cindy.

"It will...That's why I put you in the extra absorbent diaper. I have to go to work in about 30 minutes and you're going to stay here tied up. You can just pee into your diaper while I'm gone. If I get a break at work I may be able to come back and change you if you need it. But for at least the next eight hours you need to stay tied to the bed so the rubber band under your clitty can do what it needs to do." Smiled Jack.

"It is feeling a little numb under my clitty and it feels as if I have some swelling down there." Said Cindy.

Jack lifted up Cindy's nightgown and slid his hands up into her panties and diaper and felt for her little balls. Her ball sack was indeed swollen and getting bigger and it was turning a dark purple color. He did not share this with Cindy.

"You're doing fine honey. Everything is working just right. Don't worry about a thing." Said Jack as he gently pulled her nightgown back into position.

Jack got dressed as Cindy watched and then he leaned down and gave Cindy a deep and lengthy tongue kiss. When he pulled back he looked into her eyes and apologized.

"I'm sorry to do this honey, but I need to tie your ball gag back in place before I leave. You'll be feeling the need to pee fairly soon...All you need to do is relax and let it flow out your clitty. The more you relax the easier it will be. Try to relax and sleep while I'm at work. In about six hours your balls will become useless, and if they die, your body will naturally absorb them. You'll be the girl you always wanted to be."

Before Cindy could say anything the ball gag was back in her mouth and tied behind her head. Jack left her tied to the bed on her back spread eagle as she heard the sound of the door locking. She was alone and could not move or make a sound and she was feeling her balls slowly being destroyed forever.

Cindy tried to close her eyes and snooze and dream about making love to Jack. She felt a growing need to pee that became stronger and stronger. To her relief, her ball sack was fully numb and she felt no pain at all. She opened her eyes and began to concentrate on peeing into her diaper. Laying down on the bed made it difficult to pee but she really had to go and with a small bit of relaxation she felt herself begin to go. At first it was a small warm squirt. Then it was quickly followed by a more steady stream and finally she felt herself filling her diaper with very warm urine. The female extra absorbent diapers did what they were supposed to do and kept her skin from being soaked in pee. She was really relieved she could pee so much just about an hour and a half after she had been tied up.

Jack did not return half way through his work shift as he said he might. Cindy peed her diaper four more times before Jack came back about nine hours after he had tied off her ball sack. Her ball sack had lost feeling many hours ago, and without proper blood flow, it was all but certain her little balls had been permanently damaged. When Jack returned he untied Cindy's ball gag but kept her tied spread eagle on the bed.

"Oh Jack, it's so good to see you. My diaper is soaked and I have no feeling at all in my ball sack." Said Cindy.

Jack gave Cindy a deep tongue kiss and then pulled back and lifted her nightgown up to take a look. Cindy's diaper was indeed soaked but had not leaked at all. Her ball sack was twice the size as it was when Jack left earlier and it had turned a very dark color.

"Baby...I think you are finished with your balls. They should have stopped working after six hours being tied as tight as I tied them. It's been three hours past that and it looks to me as a nurse, your testicles are completely dead." Said Jack as he peeked into her panties and diaper.

"You mean I'm going to physically be a girl from now on?" Asked Cindy.

"Well, you're not going to be producing any sperm, that's for sure, and I'd be surprised if your body produced any testosterone. I'm fairly sure your body will dissolve what's left of your tiny balls and your sack will be an empty flap of skin. It looks to me it will be impossible for you to ever fuck a biological female." Answered Jack.

"I don't ever want to do that! I never want to experience sex as a male. I never have fucked a biological female and I never want to. I want to be a girl when I have sex, because that's what I am; a girl. I'm so excited that you have castrated my balls. I wish my little clitty would disappear too." Replied Cindy.

"Then we're going to need to keep you injected with testosterone blocker and then I'm going to have to start injecting you with estrogen. You have so many naturally female physical traits it should be very easy for you to transition into a natural female." Said Jack.

Cindy took this opportunity to ask Jack if he would help her find a doctor to have her balls surgically removed. She did not like the feel of them between her legs.

"Jack honey, I don't ever want to experience sex as a male again. I don't ever want to ejaculate and I want to do everything I can not to have even a tiny erection in my panties. And I really don't want any testicles below my clitty. Can you help me?" Asked Cindy.

"I do know of a doctor at the hospital who can help you. But to stop your ejaculations you'll need to have your prostate removed in addition to your balls. Without your prostate and testicles you will have nothing left sexually that will make you a male. You will have to be a female." Replied Jack.

"That's exactly what I want! I love being a girl and I love having you as my boyfriend." Said Cindy.

The two of them met with the doctor and a date for the final surgery was arraigned. Cindy was a little bit nervous but she was so quickly in the operating room and under anesthetic that she did not have time to change her mind. Before she knew it, she was waking up in the hospital with her prostate and testicles completely removed. All that was left between her legs was a very tiny bump that was the head of her penis. In the next three months, as she healed from the surgery, the already tiny shaft of her penis shrank away to almost nothing. She had no choice but to sit down to pee and she never again had any sensation at all of an erection.

While Cindy recuperated from her surgery she engaged nightly in oral sex with Jack. She perfected licking and sucking his cock into a full, rock hard, erection and willingly swallowed every drop of semen he ejaculated into her mouth. She really became good at bringing Jack to climax in a way that he enjoyed. She swallowed so much semen she had way more sperm inside her body than she ever did when she had balls.

It was almost seven months after her surgery and Cindy had healed very rapidly. When she was naked and spread her legs open there was nothing between them except for a tiny bump that was the head of her penis. The surgeon had removed all of her ball sack and she was totally smooth between her legs. Cindy started asking Jack if he would have intercourse with her by inserting his erect cock up her ass.

"I've been looking forward to this moment for a long time honey, but first we're going to have to stretch you out with a couple of butt plugs so I'll be able to get all of me inside you." Said Jack.

"How long will that take?" Asked Cindy.

"At least a month. Then if we have intercourse on a regular basis it will be easy and pleasurable for both of us." Replied Jack.

"Can we start now?" Asked Cindy.

"Of course; I've got the smaller of the plugs already in anticipation of this moment." Said Jack as he went to his dresser drawer.

"Take off your panties and lie on your back." Instructed Jack.

When Cindy did as she was told, Jack put lube in her ass and on the butt plug. He then slowly inserted the plug into Cindy as she gave a soft moan. When the plug was fully inserted Jack told Cindy to pull on her panties and keep the plug in place for a least a couple of hours. This exercise went on for about a week and then Jack used a larger butt plug with Cindy. As Jack inserted the plug Cindy moaned in pleasure and easily took the larger plug as she had learned how to relax on insertion.

Another week went by with the larger plug as Cindy kept it inserted at least 3 hours every evening. Cindy never missed a night of oral sex with Jack feeling extra pleasure in her butt when Jack ejaculated into her mouth. Cindy was ready to complete her transition to complete femininity.

"Jack, instead of my butt plug tonight, I want to put on my delicate baby doll nighty you like so much and I want you to fuck me like the girl I am. I want you to pull off my baby doll bloomers and lay me on the bed on my back and I will lift my legs into the air and have you insert your sexy, hard, cock inside of me as deep as you can. Then I want you to thrust back and forth as hard as you can until you ejaculate your manly load as deep inside my body as possible."

Jack was more than happy to do this to Cindy and the two of them were surprised how easy it was for Jack to insert his hard, thick penis deep inside Cindy with nothing to get in the way. When the two of them were deeply joined together Jack stopped for a moment and looked into Cindy's eyes and leaned down to tongue kiss her in a way he never had before. Cindy felt the full length of his erect cock inside her body and she could sense his cock throbbing with every beat of his heart.

"It's time for me to fuck you little girl." Said Jack.

"Oh my God honey...I am so ready for you! Fuck me baby! Fill me with your seed! Fuck me as hard as you can. You have no idea how much I wish I had an egg inside me so I could have your baby! I'm your girl, and I want to be your wife! Fuck me honey...Fuck me now." Gasped Cindy.

With that, Jack plunged in and out of Cindy with his dick and in only a few moments he began to gasp for breath and Cindy felt his hot semen shooting deep inside her body.

"Oh my God baby! I've never cum this hard before! I'm so in love with you I can't stand it! I want to fuck only you the rest of my life!" Shouted Jack.

"I do too Jack! I had surgery to make me your girl and I want to be your wife...I love you so!" Squealed Cindy.

Cindy and Jack were married in a church in front of a group of mostly Jack's family and friends. Cindy looked beautiful in a satin and lace white gown which concealed beautifully feminine lingerie. Cindy was at the height of her femininity and it was impossible to tell she had a tiny, shaft less, little penis in her panties.

Cindy assumed her role as a loving housewife and she and Jack have been married for over ten years. Their married sex life is as hot today as it was on their wedding night with Cindy filled inside her body with Jack's sperm at all times and loving it.