Chapter Seven
On Friday Angie had an appointment at one down at the courthouse. Seeing it was more or less a social call she left me at the office. She told me I could leave at five and come right over. She knew I already had my suit in the car for Monday.
Believe me five o'clock couldn't come soon enough but of course the afternoon dragged on and on. I though about leaving early but that would have put me at Angie's house early, and if she wasn't at home I would have to wait outside. I'm sure that would have made me look desperate. So at exactly five o'clock I made a mad dash to my car.
When I pulled into her drive way Angie's car was already there. After getting my suit I walked up to the door and rang the door bell. I waited patently but there was no answer. After a few minutes I rang the door bell a second time. A minute or so later Angie opened the door.
She looked disheveled. Her hair was wild looking, like she had not brushed it all day. Her makeup was streaked and her lipstick was smudged. Even the robe she was wearing looked like she had thrown it on in haste.
"Sorry Jack I got home early and decided to take a nap. Please come in." She told me as she stepped aside to let me in.
As soon as I walked in the door Angie hugged me tight as if she was afraid of something. She also seemed like she was getting her bearings. After hanging on to me for a minute or so she said. "Let me pop dinner into the oven and we'll go up stairs." Still slightly out of it Angie staggered toward the kitchen. A few minutes later Angie came back in to the hall and led me up the stairs by wrapping her arm around my waist.
When we entered the bedroom I saw the room looked a mess. The bed spread was thrown on the floor and the sheets on bed were all bunched up. The top mattress was slightly askew. Before I could take in the rest of the room Angie started stripping off my suit.
When she pealed off my shirt her hands were all over me. She rubbed her hands over the red satin cami I was wearing making sure to rub the material over my chest and she playfully pinched my nipples. When she unbuckled my trouser and let them fall to the floor she rubbed her hand over my panty covered bottom while she kissed me passionately.
When she pulled her lips from mine she said. "You look so sexy in your lingerie I hate to take it all off, but we must get you in the shower as I'm sure you need your legs shaved." She reluctantly finished undressing me then took me in to the bathroom.
On the bathroom vanity I saw an empty disposable douche like the one she used last Sunday after we made love. I couldn't imagine it had been there that long so I assumed she had used it recently. Before I could noticed anything else about the bathroom Angie pulled me into the shower.
In the shower we kissed and washed each other. I made sure to get all the smeared makeup off Angie's face. We also made sure our private places were very, very clean. That was the first time Angie ever touched my ass hole. She rubbed the soapy washcloth over it for several minutes while she kissed me deeply. I can't say that wasn't pleasant though I wondered why it felt so good. I mean a straight guy isn't supposed to like that sort of thing.
After we were as clean as we could get Angie grabbed the pink disposable razor and her shave gel and went to her knees in front of me. After pulling me out of the direct spray of the shower head she applied shaving gel to my left leg before she slowly shaved my leg with long strokes. It was quite erotic to watch and it felt really good too. I could honestly say I could've gotten a hard on from it, but I had gotten hard on the drive over and my erection had not gone down since.
After the fronts of my legs were done she went after my genitals. At first she shaved the pubic bone area before she started on my balls. I don't mind saying having the razor that close to my scrotum was nerve racking, but Angie shaved me without nicking me in the slightest. She even had me raise my one leg so she could shave the area between my scrotum and my asshole.
Once my front was done Angie turned me around and started on the back of my legs. She even covered my butt with shave gel and shaved it as well. I had expected this but what she did next surprised me completely.
Once she was done shaving my bottom half Angie put down the razor and started kissing my ass cheeks. Her lips moved over both cheeks and I even felt her lick each cheek several times. What really shocked me was when I felt her tongue slip between my cheeks. I couldn't stop the moan from escaping my lips, which told Angie I liked how her tongue felt.
She didn't stop there either. Once she saw I like her tongue between my cheeks she went deeper and soon she was running her tongue over my anus. That felt wonderful and confusing at the same time. I was confused because I wasn't gay but was moaning as her tongue licked at my hole. God it felt so good and yet so wrong.
Angie kept up her assault on my anus as I moaned and yes even a squeal leaped from my lips. It felt so good I nearly melted from the pleasure her tongue was giving me. That was until I felt her tongue trying to pierce my hole.
When I felt her tongue try to push its way into my hole I clamped my anus shut to keep her out. That was just wrong, she shouldn't do that. Angie was persistent. After trying to push her tongue into me and finding no success she took my balls in hand and started playing with them. This caused me to relax enough to let her tongue slide into me. I can't tell you how good that felt and I squealed like a girl as her tongue pumped in and out of me.
When I thought I couldn't take any more and I was going to pop Angie pulled her tongue from my ass and spun me around. This time there was no licking of my balls or my shaft. This time Angie took my cock straight into her mouth and started sucking like there was no tomorrow. Her mouth moved like lighting as her left hand caressed my balls.
Her right hand, which had stayed on my ass cheek, slowly started sliding over toward the crack between my cheeks. Less than a second later her finger were touching my anus in a very sensuous way. I could actually feel my anus start to open for her finger.
When I felt her finger pierce my opening I groaned out as my orgasm hit me. Instantly I was pumping squirt after squirt into Angie mouth. She in turn started fucking my ass with her finger before adding a second one. I swear it was the strongest orgasm I ever had. It felt like I squirted a quart of semen into her mouth.
Before I could completely recover from my orgasm Angie was kissing me. When her tongue slid into my mouth the sperm load I had just pumped into her mouth flowed into mine. I guess I didn't cum a quart like I thought but it was a very generous amount.
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Literotica: Transsexuals & Crossdressers: Jackie Pt. 02
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index : Transsexuals & Crossdressers : Jackie Pt. 02
Jackie Pt. 02
by Scriblerc
Once we had swallowed my sperm Angie pulled her lips from mine and said. "I see you enjoyed have your ass played with. I think we should explore that in greater detail. Don't you honey?"
As she turned off the water to the shower and started pulling me out I said, "I don't think that's a good idea."
"Why on earth not baby. I could tell you liked it. I never heard you squeal before like you did in there. Surely you must have loved having my tongue and finger in your bottom?"
How could I possibly tell her I didn't like it when every thing point toward the fact I did? With no other argument I went for the logical argument. "It felt good but it's a gay thing. Only gay men find that kind of stimulation pleasurable."
Angie giggled as we toweled each other off. She then smiled down at me and said. "Honestly you say the funniest things. Do you actually believe a straight man's anatomy is any different than a gay man's anatomy?"
"Well I guess not but gay men are different." I told her even though I knew I was losing this argument.
"Of cause they're not honey. What a gay man finds pleasurable a straight man should also find pleasurable. It just depends on who they're seeking that pleasure from. Now please shave extra close so I don't feel any stubble. Mean while I'll get your clothes ready."
It took me about ten minutes to shave and dry my hair. In that time Angie not only got the clothes out she wanted me to wear but she also striped and remade the bed and got dressed herself.
When I came into the bedroom she was wearing a silk black dress that was extremely short. It had a loose fitting skirt and a plunging neck line that showed a lot of cleavage. She had on three inch stiletto heeled sandals. Her hair was brushed out like it normally is with plenty of curls cascading down her back. She was sitting at her makeup table making up her face.
When she noticed me in the room she said. "Have a seat on the bed love and I'll be with you in a few minutes. I need to take dinner out of the oven and let it cool then I'll be back to help you dress."
I sat on the bed like I was told and looked around to see what clothes she had in mind. As far as I could see there wasn't anything out that I could wear. But Angie didn't give me much time as she came back in only a few minutes carrying two glasses of wine.
After handing me a glass of wine she went to her makeup table and picked up something before coming back to sit on the bed next to me. She took my hand in her and said. "Jack honey I have a confession to make. As I told you before I like both sexes. As far as men are concerned I could take them or leave them.
"I don't like the way they always think they can tell me what to do or how to act. I like being the one in charge and most men can't handle that. Women on the other hand are different. They usually don't mind following my lead. Besides that, they are more fun to be around. I guess that's why I haven't married yet. I can't find the kind of man I'm looking for. The kind that has all the qualities I look for in a woman yet is still a man."
When Angie stopped talking I thought this was the brush off. I had seen it before and I knew she was telling me it was over. I didn't say anything, as I was afraid she would end it right then.
Angie was silent for a minute or two before she said. "What I'm trying to say is I like you a lot and I would like to continue our relationship. I think you could be just what I'm looking for in a man and girl. You very smart and you don't mind taking orders from me. You don't mind when I decided where we should eat or where we should go. You seem quite happy letting me lead you."
I saw this as an opening so I said. "I don't mind you telling me what to do or where we should go. I really like you to and I would hate if we ended our relationship."
She squeezed my hand and said, "I would hate it to love, but there are a few things I think you have a problem with. Like who pays for what. You always complain when I pay for dinner, when we both know you can't possible afford the restaurant we go to."
I was about to tell her I could live with that but she silenced me with her finger to my lips and said. "Also your reluctance to do things we both know you like because you think they're gay. Sweetheart I know you not gay and so do you but if you enjoy something and it doesn't hurt you, you should do it. Like earlier in the shower we both knew you loved having my tongue on your pretty asshole and you loved having me finger fuck you back there. But you had to say you're not gay and it spoiled the moment for me."
"I'm sorry I didn't want you thinking I was weird." I told her.
Angie giggled and said. "Honey if I thought that was weird I wouldn't have done it. I enjoy giving you pleasure as I know you enjoy giving me pleasure. You know I get turned on when you put on sexy girl's clothes for me, which was why you started wearing them. Now I'm sure you also like wearing them. Do you?"
This would be the first time I had to admit I like wearing them so I said. "I like wearing the lingerie you gave me. They feel good but I really like it that you want me to wear them."
Angie leaned over and kissed me for a second or two before she continued. "I know you do love now if we continue this relationship I want you to be as much a girlfriend as a boyfriend. That means when I want my girlfriend I want her every bit a girl. That means you have to do your nails, fingers as well as toes. Your face has to be made up like I make up my face. You also must act like a girl so no one can tell you're not a real girl.
"When I want a boyfriend then you must act like the man you are. If it bothers you I pay for our meals or what ever else we buy then I'll give you the money to pay but no more questioning who pays for what. Of cause you will do everything I tell you and at least try every thing I want you to try. That means no more telling me you're not gay, as I know you not. Doing things you think only a gay man would like, can be very pleasurable. Is this agreeable to you?"
I probable should have walked out at that point or at least told her no way do I agree with her. To prove how whipped I was I said. "I think I would like that."
Angie smiled her warm wonderful smile and said. "I was pretty sure you would love so let's get you dressed and then I'll teach you how to put on make up and do your nails"
Angie took my hand and pulled me gently to one of her dressers and said. "This dresser belongs to you. In it I have put all kinds of lingerie that you can wear. From this moment on you will only wear lingerie even under you male clothes."
She went though the draws showing me everything she had bought. There were panties galore, well over thirty pairs of them. There were camisoles and teddies as well as garter belts and stockings. There were also corsets bras and bustier. I wasn't sure about those, as I didn't have any breasts. Everything in the dresser was made of either satin lace or silk or a combination there of.
When she was done going though the draws she took me into a walk in closet. In there she showed me dresses skirts and tops to go with the skirts. There were a few jackets as well as a few coats. There were at least ten pairs of heels on the floor and she told me that the number of pairs of heels would grow once she learned my perfect size. Through all this I didn't see a single thing a man could wear. Obviously Angie was ready for this. "We will get to you male attire in due time I wanted my girlfriend to come first. You'll find that you will be my girlfriend far more than my boyfriend."
Angie picked out a red silk dress and a pair of two-inch heels and said. "Come along Jackie. Let's get you dressed for dinner. Oh by the way you girl name will be Jacqueline or Jackie for short. I think that will be easy to remember don't you?" Of cause I agreed with her how could I possible say no.
After laying the dress on the bed and the shoes on the floor she went over to the dresser, or should I say my dresser. She pulled out a pair of panties, stockings a bra and a waist cincher with garters attached.
She handed me the stockings and said. "You know how to put these on by now don't you." Of course she knew I did.
While I put on the stockings she went over to her dresser and pulled out a box plus a white tube. When I had the stocking on she said. "You don't have to glue these on all the time, but when you're going to be a girl for a few days I want you to glue them in place. Now watch what I do."
She opened the box and pulled out what looked like a breast. It had the same shape as a breast and there was even a nipple and an areola that was darker then the rest of the breast. She told me it was a breast form for women that lost their breast from cancer.
I watched as she applied glue to the back of the breast form before placing it on my chest. The glue was cold and so was the breast form but I was told that it should warm up with my body heat.
Once she had the first breast form where she wanted it she told me to hold it in place while the glue cured. She then applied the second form to my chest. While I held the breasts in place she wrapped the waist cincher around my middle and zipped up the front. She then went around back and started pulling on the laces till the cincher was quite tight.
Once she had the cincher as tight as she could make it she said. "That will pull you sides in and give you the hourglass figure all us girls want. I bought you several and I think you should wear one all the time, even at work. They will train you body to give you the shape without it, at least for a while."
By the time she had the waist cincher tighten the glue that held the breast forms in place was dried so I was able to attach my stockings to the garters. The panties came next and then she gave me the bra.
Seeing I never worn a bra before I wasn't sure on how to put it on. It looked simple enough but I couldn't get the clasps to connect with my arms bent around behind me. Angie giggled for a minute or two before showing me the easy way to put one on. Once she showed me to put it on backwards then once the clasps are connected turn it around and slide you arms though the straps it made more sense and it was a hell of a lot easier.
Once the bra was in place Angie put her hand on the satin covered breast forms and said, "MM very nice, they look so real once you're wearing your bra. I thought the B cup size would be too small, but on you they're just right. They're big enough to give you a womanly shape but not too big to draw unwanted attention to them."
After Angie massaged my breast for a minute or two she handed me my dress. I was going to pull it over my head like a shirt but Angie stopped me and told me a real girl would step into it so she didn't mess up her hair, as most all girls would have her make up and hair done before putting on her dress.
I put the dress on as instructed and Angie helped zipping up the zipper. The dress was rather short but no shorter then Angie's was. Instead of the plunging neckline like Angie's dress the front of mine came up and wrapped around my neck like a collar. Angie told me it hid my Adams apple that girls don't have. It actually felt extremely comfortable and I kind of liked it.
As I was putting on the heels Angie said. "We'll start you off with two inch heels until you get use to them. Then you can graduate to a three inch and then a four inch. I want you in heels for the next day or so and the rest of the week you should wear them when you at home. By next weekend I would like to see you parading around in heels like you've worn them your whole life."
The heels weren't that bad as I took my first steps. The wide heel gave plenty of support and seeing they really weren't that high I found walking in the rather easy. Of cause I took too long of a step and Angie quickly corrected me. Girls don't walk like truck drivers she said.
We went down stairs to eat dinner. Even though the lasagna had been out of the oven for almost an hour it was still quite warm. Angie said it was the perfect food to teach me how a girl should eat. She cautioned me to take tiny bites of food and to keep my napkin handy at all times. I never noticed how differently a girl eats compared to a guy. Even drinking a glass of wine was different from the way you held a glass to the way you sipped from it.
Seeing Angie had a glass top table she was able to see how I sat and she was constantly telling me to keep my legs together. I found this really difficult, as I never had to worry about it before.
After dinner I did the dishes while Angie watched. I guess she wanted to make sure I did them the way a girl would but I really didn't think there was a difference. That was until I bent over to put a pan away and found out a girl bends at the knee not at the waist.
Once I was done with the dishes Angie took me upstairs where she went to work on my hair. She told me everything she was doing so I could repeat it the next time. She then sat on my lap and started on my makeup. This she did with out me being able to see what she was doing.
First she took a pair of tweezers and started plucking my eye brows. She told me seeing I had blond hair no one would notice the new shape. This took quite some time before she picked up an eyebrow pencil to darken my eyebrows.
She put mascara on my eyelashes and then used eye shadow above my eyes. She applied a creme to my face and smoothed it on my cheeks and chin. She used rouge to highlight my cheek bones that I didn't have and ruby red lipstick on my lips.
Once my face was made up she took my hands and glued on press on nails. After shaping them she started applying nail polish. This I watched as I was sure I would have to do it again myself. This took quite some time, as we had to wait for the coats to dry before she put on another coat.
As a final touch Angie took out my small gold post and put in large hoop earrings in my ears. It was the heaviest thing I ever had in my ears and it felt like my earlobes were being pulled down by the weight.
When she was finally done she looked me over and said. "I knew you would be pretty. I knew it when I first saw you."
Before I could ask what she meant she took me over to a full length mirror. What I saw staring back at me actually surprised me. I had thought I would look the same as I did before just with make up. But what I saw staring back at me was quite pretty. My face looked so much different then it did without the makeup. It actually looked very feminine. I was sure somebody could tell I wasn't a real girl but I sure couldn't.
"Well what do you think Jackie?" Angie asked after I stared at myself for a while.
"I think you did a wonderful job I didn't think I could look this good." I told her unable to take my eyes off the mirror.
Angie slid her arm around my waist and said as she pulled me closer. "You look very pretty and I doubt anyone could tell you're not really a girl. But the real question is how do you feel about wearing a dress? If you're not comfortable in it I'm sure you'll give yourself away."
I looked at myself in the mirror once more. I couldn't get over how feminine I looked. Not only that but I felt really comfortable dressed. It was odd how natural it all felt. It all felt some how right.
"I know this is going to sound weird but I like how the dress feels on me. I like how I look and for some reason it feels right to me." I told her though I couldn't look her in the eye when I said it.
Angie pulled my chin up and said. "Sweet love I knew you would feel this way. That's why I was so attracted to you." Before she continued we started to kiss me.
We kissed for a long, long time and I was sure the lipstick we had on our lips was gone by the time our lips separated. As soon as Angie saw my lips needed repairing I was take back to the makeup table and shown how to put on lips stick.
After my makeup was repaired Angie gave me lessons in deportment. I was taught how to stand several different ways from demure and innocent to provocative and alluring. I was also taught how to sit and where I should put my hands. I even worked on my voice till my female voice sounded sexy and slightly smoky.
Through out the evening we kissed constantly and each time we were done kissing I had to repair my makeup. Not only my lips but also my eyes had to be redone, as did my cheeks
Now you might think this would have been tedious, but it wasn't anything of the sort. I had fun dong it and it seemed like Angie was enjoying herself as well. Before either of us knew it, it was nearly three in the morning.
Angie stretched and said with a slight yawn. "I guess it's bed time we can practice more tomorrow."
Going to bed didn't mean we were going to sleep. After changing into nightgowns we lay on the bed together and were kissing almost instantly. Angie was in charge as she guided me into what she wanted.
I made love to her breasts bring her to several orgasms with my lips and my tongue. She then had me go lower till I was licking her pussy and clit like it was my last meal. She even had me use my fingers to finger fuck her as I licked her clit to another orgasm.
After Angie had cum on my tongue several times she looked down at me and said. "Honey do you remember what I did in the shower to your bottom. I would really like it if you would do me the same way."
I was not surprised by her request. I would have bet money the moment she licked my ass I would be licking hers. To tell the truth I was looking forward to it as I had often thought her bottom looked so good and I had often thought it was made for kissing. Without the slightest hesitation I rolled Angie over on to her tummy and started kissing her perfect bottom.
Her ass cheeks were as smooth as, well as smooth as a baby's bottom and her skin felt as soft as velvet. Kissing and licking her sweet cheeks wasn't what I would call a chore and in minutes I had covered her bottom in kisses and licks.
After her cheeks were thoroughly licked and kissed I went after the crack between her cheeks. As soon as my tongue made contact with her butt cleavage Angie moaned so sweetly I just had to continue. My tongue slid from the bottom near her wet pussy to the top where her cheeks came together. On each pass Angie would moan and I would go a little deeper.
I thought her anus would have a foul odor but I was determined to give her the same pleasure she gave me. When my tongue touched her anal star for the first time I was surprised that it didn't have an odor of any sort. In fact it smelt and tasted slightly sweet like she had coated it with honey.
As soon as my tongue touched her anus Angie pushed back with her hips and said. "Oh god yes Jackie lick my hole, fuck my hole with your sweet tongue."
I really didn't think about putting my tongue inside her hole but I really didn't have much of a choice. As I was licking her tender opening it opened and practically swallowed my tongue. My tongue started going in and out of Angie's asshole while she squealed in delight and her finger danced on her clit.
It wasn't long before Angie was gasping as another orgasm racked her body. I didn't stop my tongue's assault on her rear entrance as she humped my face with her sweet ass.
Angie's orgasms seemed to hit her one right after the other for a good ten minutes while my tongue drilled into her hole. Finally she pulled off my face and begged. "Now Jackie give me your clit. Fuck my pussy with that sweet clit of yours."
With Angie kneeling on the bed and her bottom staring me in the face I could only imagine she wanted it from the rear. I knelt behind her and pulled down the panties I was wearing enough to get my dick out. A second or two later I slid my manhood into her and she gasped for the first time. Her pussy was hotter then I ever felt it and her juices were running like a river. At the same time her hand reached back and started rubbing her clit as if it was on fire.
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Literotica: Transsexuals & Crossdressers: Jackie Pt. 02
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index : Transsexuals & Crossdressers : Jackie Pt. 02
Jackie Pt. 02
by Scriblerc
I didn't last long as I stared down at Angie's beautiful bottom. With in a minute or two as my mind thought on how I would love to fuck her bottom I shot my load into her sweet pussy. With the aid of her fingers Angie came as well with an ear splitting squeal that seemed to shake the windows in the room.
Before my cock even started to soften Angie pulled off and fell flat on the bed. I stayed on my knees and watched as Angie came down from her orgasmic high. Her body shook and as it did so tiny little squeals would exited her lips.
When I had thought she had passed out she rolled onto her back and said. "Please Jackie lick me clean like you did last Sunday. I love it when you clean me." How could I possibly resist her pleas?
I cleaned out her pussy of the mixture of our love making. Each time my tongue entered her I felt her squeeze her muscles so another globule of pearly white cream would slide onto my tongue. This time Angie was far too exhausted to roll us over so she could sit on my face, I did my best to clean her love nest.
After cleaning her pussy to her satisfaction she pulled on my head till I crawled up and we kissed. When she broke the kiss she said. "You are wonderful I'm so lucky to have found my perfect lover." I can't tell you how proud I felt at that point. We kissed for a few minutes longer before we fell a sleep in each other's arms