Getting Nailed

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"We are going to have a series of events today and tomorrow that will test your limits Jacquelyn, but you will not be hurt physically or professionally. Just follow instructions and all will be fine."

I trusted Sarah completely and started following her directions. First I got my shower with Sarah watching to make sure I didn't masturbate and then I shaved twice. Sarah cleaned my cock and balls with the cold alcohol and using the surgical tape, she flattened my sex into the body recess again. I was now a sexless being with only my mouth and ass/cunt for sexual pleasure. It hurt a bit getting my balls shoved up into my abdomen, since Sarah had been giving be the blue balls chastity treatment all week, but she was satisfied with the flat look when she finished. Next she had me put on the pink silk panties and matching camisole, garter belt and hose and when that was all finished, she had me sit at the dressing table and put on bright red lipstick to her satisfaction.

Sarah put mouse in my hair, which was getting a bit long for work since I had not been able to get it cut with my busy schedule, then she combed it and blow- dried it into a sweeping feminine style. I looked into the mirror and wondered how much sexier Sarah could make a man look!?

Sarah helped me into the bedroom slippers and had me put on my silk robe.

"We are going over to Frank and Lori's house to get something very special Lori made for you".

"I can't let them see me like this, please don't humiliate me like this!"

"You do not have any choice and Lori is very excited to meet Sissy Jacquelyn and if you don't get moving, I am going to get my switch".

The switch was not even a possible choice for me so I got up and followed Sarah out our back door. Our back lots were connected and we had put a gate in the fence so we could go back and forth without walking around the block. The patio door was open and we let ourselves in.

"Lori, where are you?"

"I am in the bedroom Sarah, bring Sissy Jacquelyn back to meet me!"

Sarah took my hand and pulled me to Frank and Lori's bedroom. I knew Frank was not home, because I had cancelled out of our golf round and he had teased me all week about being "pussy whipped" for staying home with Sarah. Frank and Lori both had a very tough childhood. Lori was born is South Korea to a poor young Korean woman and an American GI. When she was about 8, Lori and her mom moved to the states with the help of an uncle. By the time she was 10 her mom had died in a car wreck. Her aunt and uncle raised her after that. As we got to know Lori (she goes by Lori because it sounds a lot like her Korean name) she told how her uncle has sexually abused her and threatened her with being sent back to Korea as an orphan if she complained. She had to work in his clothing sweat shop everyday sewing and he kept her around till late when he could use her for his sexual needs. As soon as she graduated from High School she took off and went to college with scholarships and work- study. She has never gone back to her uncle's house again and talks with her aunt rarely.

Frank was born to a Mexican girl and a Black kid who took off and never saw his son. Frank got beat up constantly growing up and his mothers family called him a "half-breed" until he got so tough that nobody wanted to tangle with him. By the time he was 16, he was sent to the juvenile home for boys who had run out of options. He never told me what he did to get sent there, but he said he was a real bad ass for a 16-year-old. When he was in juvenile lockup, he connected with a teacher who convinced him that he could turn his life around if he wanted to. With the teacher's help, Frank got his HS diploma and was admitted to college by the time he turned 18 and left juvenile. The teacher kept in touch with him and encouraged him to stay away from his old life and stay clean. Frank never looked back and cut off all contact to his alcoholic mother and the rest of his family. He said he never missed them and could not think of a reason to see them.

Frank and Lori met in college and because of their backgrounds, felt like soul mates from the start. They fell in love and got married their senior year. Now we were there only "Family" and Lori and Sarah were like sisters. Frank was very macho at times and he didn't let himself get very close to anybody besides Lori, but I was as close to Frank as anyone could be. Lori tells Sarah everything and she told Sarah that her uncle made her give him blowjobs at the factory. She learned to hate it and even though she loved Frank in made her sick to go down on Frank's big dick. I had seen his cock in the locker room and it was bigger flaccid than my dick was hard. I had no idea how big, but Lori had described it to Sarah as a real monster.

"Come closer Sissy Jacquelyn and let me see you."

Lori looked beautiful with her face framed by her long dark hair on the satin pillowcase. Frank and Lori were both gorgeous. They had that mixed race exotic look and I swear they had the best features of all the mixed race genes in their background. When they were in college, them both did some modeling to earn money.

"Don't be shy Sissy Jacquelyn, Lori has already seen you."

Now I knew who owned the other hands.

"I have a present for Sissy Jacquelyn." Lori told me.

"Thank you I muttered"

Lori handled me a wrapped package that was too nice to open.

I just stood there in shame and humiliation till Sarah spoke and told me to open it. I worked the wrapping off carefully and when I got past all the layers of tissue I found a very fancy corset. It was made of silk, had heavy boning and had been hand made. The corset had half cups for tits and ended with garters to hold up a pair of hose.

"You better thank Lori for such a fine handmade gift."

I made my best effort to thank Lori for the corset, but when I finished Sarah said that it was not good enough and that words alone could not show my appreciation.

"Why don't you offer Lori something special in return for such a fine gift?" Sara prodded me.

I had nothing to give Lori and I did not know what she could possibly want in return.

"Lori, thank you very much for such a sweet gift and if there is something I can do in return I would be more than happy to try giving you something as wonderful."

"Well Sissy Jacquelyn there is something you can give me that would be just as nice a gift. You see Frank does not like to go down on me and lick my clit because in the world he grew up in that was just the nastiest thing. We are quite a pair, I can't stand to give Frank head and he can't stand eating pussy. Sarah says you are an expert at cunt licking and she has promised that I can borrow Sissy Jacquelyn for cunt eating when she knows about it. So, would you give me my first real cunt licking Jacquelyn?"

I looked at Sarah and she nodded her approval and left the room. I was standing there holding a corset and being asked to eat the pussy of one of the most beautiful women I know.

"Yes Lori, I would be happy to eat you pussy. I don't think it is as nice a gift as your gift, but if that is what you want from me I will be happy to give it to you."

Lori pulled the sheets back and I saw her naked form under an expensive silk and lace bedroom gown. She slowly pulled up the gown until I could see her pubic hair peaking out. I could not take my eyes off her pussy as she slid her hips to the edge of the bed.

"Kneel down and make me happy with your mouth, but just your mouth. You can not touch me with any other part of your body." Lori told me.

I was on my knees in a flash and as I leaned forward I saw her cunt up close. It was strange looking and seemed to have an unusual odor. I started kissing her feet and legs on my way to her pussy and as I got closer I was looking right into her cunt. Then it hit me, Frank had just fucked her before we came over and she had been laying in bed with his sperm in her pussy just for my humiliation. I looked up and Lori just smiled.

"Sarah says that Sissy Jacquelyn loves to eat sperm so I saved you some. I told Frank all week that my stomach was upset and that I didn't feel well enough for sex. It was a hard week for Frank because I never made him go without for more than 2 days before. I have 5 days of sperm in me and Frank came twice before he quite. Now beg me like Sarah says you do!"

I started begging for Lori to let me suck Frank's cum from her pussy.

"Please Mistress Lori, let me lick your sweat pussy and clean Frank's sperm from your cunt."

I must have learned to beg well, because Lori grabbed my hair and pulled my mouth to her cunt. It was a mess. Frank's big dick had left her hole wide open and it was full of his sperm. The more I licked it up, the more excited Lori got and the more her cunt flowed with her pussy juice. As she responded to my tongue, her clit was swelling with excitement. Her clit is the biggest I have ever seen. It poked out from her pussy lips like a miniature cock. The end of her clit was like the tip of my little finger. Sarah's clit is only a small little nub, but this clit was big enough to suck into my mouth like a tiny cock. I sucked her clit between my lips and ran my tongue over the tip until her body went rigid with orgasm. I went back to licking her pussy lips but I could not clean her up fast enough and the combined love juices were running out of her cunt and down her ass.

"Lay on your back on the floor!" Lori told me.

Lori got up and sat her gaping hole right down on my mouth. I just had to swallow as Frank's sperm and Lori's pussy juice fell out and into my mouth. A big glob of Frank's cum slid down my throat and made me gag. I managed to keep from throwing up and Lori was starting to rock her pussy back and forth on my face. Her wide-open cunt was smearing slime from the tip of my chin to the tip of my nose. I could only make brief contact with her clit as it slid up my face and again when it came back down to my chin. She kept up her pelvis motions for several minutes while she built for a grand orgasm. When she came, I thought she was going to break my jaw and nose. As she came down I gently licked her pussy lips and avoided her very sensitive clit. She slowly relaxed her leg muscles and pulled herself off my face and crawled back into bed. I couldn't quit thinking about the girl's clits, very different in size but both are very sensitive.

"How did you like Sissy Jacquelyn's tongue Lori?"

I looked at Sarah to see that she had been recording a video of the whole thing.

"It was fantastic, Frank will never eat me out. All he will do is kiss me lightly on my pussy mound and no more! I know you told me how good Jacquelyn can eat pussy, but that was fantastic, almost as good as fucking Frank's big dick."

"Thank Lori for letting you eat Frank's sperm from her pussy Sissy Jacquelyn!"

"Thank you for feeding Frank's sperm to me, eating sperm makes a sissy slut like me horny! Thank you for letting me taste you pretty pussy Mistress Lori it was very sweet!"

It was true, eating a strange pussy and being made to eat another man's sperm was making my dick hurt in its surgical tape prison. There was no room for me to get an erection, but my dick was trying as hard as it could. My crotch was throbbing and twitching and it had no stimulation at all.

"Time to try on your new corset Jacquelyn!" Sarah informed us.

Sarah and Lori led the way to the family room with the beams and vaulted ceiling. Sarah quickly put the cuffs on me and hoisted my up tight using one of the beams in the middle of the room. I was still in the high heel slippers and knew I was going to get uncomfortable quickly. Next, them put the cuffs on my ankles and pulled my legs out a bit and tied me to the furniture. I was again stretched tight and could only shift slightly.

"You are going to love having this corset on when you see how nice it makes you look Jacquelyn!"

Them started by unhooking the front of the corset. It took them several minutes because there were so many hooks.

"Lori wanted your corset to lay very flat, so she sewed in all the front hooks with no gaps. Isn't she a special friend to make your corset so well Sissy Jacquelyn?"

"Thank you Mistress Lori for making such a special corset for Sissy Jacquelyn!"

It too several more minutes to hook the front closed again. This thing fit me like a second skin. Lori could sew anything after working in the factory and she had taken my measurements for an exact fit.

"Now we can lace it up for you Sissy Jacquelyn! You may beg us to lace you into your silk and lace corset."

"Please Mistress Sarah and Mistress Lori, lace me into my corset and make me look like a real sissy slut!"

They started working the laces. It took 30 minutes to get me down in the waist like Sarah wanted. It hurt like hell as them pulled the laces tighter each time I let out my breath. By the time they were done, I must have lost 2 or 3 inches off my waist and it made my hips look bigger.

"It looks good, but it is missing something Sarah." Lori proclaimed.

"Not to worry, I have just the perfect items to complete the look."

Sarah went to her bag and brought out 2 breast forms that looked like perfect breasts.

"I got you a C cup Sissy Jacquelyn, I know a slut like you wants breasts as big as a cow, but Lori and I don't want to get jealous of your new tits!"

Lori placed each one in the empty cups, checked the fit and them took them back out.

"It is a perfect fit, but I want you to experience the feel of breasts attached to your chest, so I am going to attach them to you with a special liquid adhesive. It is made so women with mastectomies can go swimming without the breast form slipping out of the suit. It holds strong and is water proof!"

Sarah coated the back of each breast form with the glue and placed it back in the half cups of my corset. She positioned the artificial breasts carefully and made sure they were in balance. The glue felt cold, but quickly dried and set.

"These are the very best breast forms I could buy and they will jiggle and bounce just like real ones. The nipple is molded in the breast form and I selected your new tits with the largest erect nipple available. Mistress Lori made the cups on your corset to support your new tits but leave your nipples exposed. I want you to look hot and slutty all the time and these are perfect tits for Sissy Jacquelyn.

When they were convinced that the glue was completely dry, they released me from my suspension. It hurt like hell to lower my arms and put more pressure on my stomach. I walked around a few steps to get the kinks out of my legs and suddenly I saw myself in the mirror. I was shocked with the image with naturally jiggling breasts. I really had a woman's shape with the breasts and tightly laced waist. The heels made my legs look great and my hair was shaped quite nicely. My face was a mess.

Lori has smeared her and Frank's cum all over my face and my lipstick was smeared just as much. It made me look like a big whore who had fucked the whole navy. I was appalled with my face.

"Please can Sissy Jacquelyn clean her face so she doesn't look like such a whore?" I begged.

"Why yes Jacquelyn, I am glad to see you taking more of an interest in your appearance."

When I came back to the family room, they both looked like the cat that ate the canary.

"We have to go now Sissy Jacquelyn, so tell Lori ta-ta for now."

"Goodbye Mistress Lori and thank you for my pretty corset and for letting me eat Frank's sperm from you pussy. It made me very horny."

Sarah took me home and I almost fell over trying to keep up. When we got home, Sarah took me back to the bedroom and told me to finish dressing. She had out a simple nylon-jogging suit for me and after I got it on, you had to do a double take to tell if I was a man or woman.

"Don't worry, after we get you in makeup you will have no problem passing as a girl!"

I didn't want to pass as a girl, it was a lot of fun playing sex games with Sarah and Lori, but I did not want to go anywhere that required me to pass as a girl.

"Time to go, you don't want to miss your appointment do you Sissy Jacquelyn?"

"What appointment, I don't have any plans to go anywhere!"

"I got you a beauty appointment and lets go before you are late!"

I started to argue, but remembered the switch. Lori grabbed her purse and went to the garage with me close behind. Fifteen minutes later, we were in a beauty shop. It was still early and no other clients were there.

"To make you more comfortable in your first trip, I got Pauline to open early."

I took my first look at Pauline and after a few seconds I realized that Pauline was a very female looking guy.

"Yes darling, I am a sissy just like you and your lovely lady asked me to help you look your best for tonight." Pauline said in a rich low voice that gave just a hint of her gender.

I could think of nothing as Sarah and Pauline guided me into the chair. The two of them talked and discussed options, made their decisions and got started. My ears were pierced, my eyebrows were thinned a bit, and my hair was clipped and styled perfectly and then the nail girl came in and started working on my nails. She had her instructions and she got started putting on her longest nails with bright red polish. I thought Sarah did my nails great last week but this was even better. I was just amazed by the look she achieved, longer redder, brighter and perfectly shaped. I think there were 5 layers of polish and 3 layers of a shiny topcoat. I am sure any movement of my fingers would catch the eye of someone a mile away. This was exciting and humiliating at the same time. My heart was pounding and my poor abused waist was restricting my breathing.

Pauline came back to do my makeup and just finished as other customers started to come in. I didn't talk to anyone, but I could tell from the looks that they were impressed and not sure if I was a tall woman or one of Pauline's transgender friends. I looked at myself in the mirror and knew that if I didn't talk, nobody could tell for sure. Sarah was grinning ear to ear as we drove away.

"I knew Pauline would be perfect for you Sissy Jacquelyn! What do you have to say for yourself?"

"Thank you mistress Sarah, you have made me look very pretty and I am so horny being made to be your sissy slut!"

It was true, my whole body was charged with an energy like never before. I was driving around town looking like a good-looking woman out with her good-looking friend. We turned quite a few heads as we drove home. When we got home, Sarah fixed us a bite of lunch took off my tape so I could pee and told me that we were going to relax the rest of the afternoon and keep my pretty new look for tonight. When I asked why, she said that it was a surprise and I just had to wait.

Now that my dick was free again, I was able to get an erection again and my tits and look kept me hard and aroused in my panties all afternoon. Sarah got out a romance movie and gave me some lingerie catalogs to look at as she relaxed and I stayed charged with sexual tension. It was early evening when Sarah said we needed to eat a bite of soup to keep our stomachs from growling, but not spoil my appetite for later. I didn't know what she was saying but went along as requested. We had a little chicken soup and cleaned up the kitchen.

"Jacquelyn, I am going to ask your permission to do something later tonight and I want you to say yes, but if you don't want me to do this thing I am not going to. It will disappoint me greatly not to get to have this experience, but I will understand if you say no. One other thing you should keep in mind before you answer, I do not think we well play Sissy Jacquelyn again if you refuse me my pleasure."

"Ask me anything Mistress Sarah, I can deny you no pleasure after all the pleasure you have given me when we play Sissy Jacquelyn sex games!"

1...678910...14