tagTranssexuals & CrossdressersSister Mary-Margret and Jenna

Sister Mary-Margret and Jenna

bytgirl_Mary©

This is not another cliché Halloween story. The fact that it happened on Halloween is purely coincidental. It is a story about a night out with my friend Jenna. I first noticed Jenna on her online profile. It was a transgender and cross dresser website. I had my own profile on there for a number of years. I had just turned forty and had been actively cross-dressing for about ten years.

I started a bit later than I wished. I had only occasionally worn women's things when I was younger but I didn't know how big a world it was until the internet came along. I had been writing erotic stories to magazines before the web came along in the late nineties. After that I posted them on websites. I usually wrote fiction with trans characters which was my favourite topic. People started writing back with feedback and wanted to see pictures of me. That encouraged me to take the next big step and go all out. I bought the clothes, wigs, makeup, shoes and all the kit necessary to take the plunge. I bought a digital camera and soon had my own photos online for all to see. I chose the name Mary-Margret for myself which stuck.

That progressed to meeting others like me and sharing experiences. I would sometimes even go out to clubs dressed up in full drag. I was really enjoying it as a part time hobby. I still had my regular mundane life with a steady job as an engineer for a telecomm company where no one at work suspected me of my off hours activities. I continued writing and even set up my own blog page. Like I said, I had been active like this for about ten years when I met Jenna.

Jenna 's photos caught my eye. She was pretty, always smiling, with wavy, natural red hair. Her body was tight, athletic and her legs were dynamite. She dressed provocatively but classy. I admired that. I estimated her age to be early thirties, much like myself when I started out. She was new but her pictures showed her out there at the clubs and in the streets dressed up and not shy about it. After exchanging photo comments we progressed to online chatting. I soon discovered that Jenna was very intelligent and sharp. That was refreshing for me. We chatted many times and exchanged emails for a while. We had not met in person because she lived a couple hours' drive away in the big city. I didn't travel there very often. I had in the past a few times and had one negative experience which kept me from going back.

Finally Jenna challenged me to make the drive and meet up with her in person. I took her up on it. She suggested a private nightclub which catered to swingers. They were very friendly to all types and cross dressers were always welcome. It would be a slightly older crowd then the nightclubs of the gay district where I sometimes felt like a grandmother amongst all the twenty something kids that frequented them. It was a good choice.

The swingers club was like a dark lounge with a dance floor, bar, and some back rooms for privacy. When I met Jenna in person that first time, the two of us mostly talked a lot and got to know each other better. She was genuinely sweet and charming. She was also even better looking in person. She had a light sprinkle of freckles which I loved. Her bright blue eyes had me captured. Her outfit was quite sexy. She wore a tight black sweater and a black leather mini skirt. She wore fishnet stockings and red stiletto shoes. She looked hot. I made sure to tell her so too.

Jenna admitted that she found me attractive too. I did my best. I had worn a short black and white polka dot baby doll dress. I had black fully fashioned nylons that were held up by my black six suspender garter belt. I wore my favourite black suede calf high boots to go with the outfit. The outfit really showed off my shapely legs which were my best feature. I wore my long, redhead wig which was my go to choice. Jenna and I danced, drank, flirted and shared lots of girl talk. We got hit on by a several guys but we tried to devote our attention to each other. We did enjoy all the free drinks though. I also learned that Jenna was married and her wife not only knew about this side of her but was also supportive. Jenna said that her wife often joined her on her nights out as Jenna.

That night was just the beginning. When we got someone to take our picture together, both of us began posing provocatively and showing lots of leg. Our photographer suggested that we kiss. For a second, it felt like the rest of the world disappeared and all was silent as our soft red lips made contact. Jenna kissed very much like a woman. She was soft and yielding. Even though the kiss did not last a long time it was an eternal moment for me. The spark was lit. I wasn't expecting anything but the kiss we shared gave me hope for more. It was late and the club was closing and both had to get up early for work the next day so we left it at that on that night. Once we stepped out onto the street, we shared another soulful, sweet kiss before parting ways.

We chatted several times after that and we both remarked about the kiss. It was unexpected but very much enjoyed. I looked forward to another possible night out with my new friend. As it turned out, the next chance we both had to meet on the same night was Halloween. Luckily, it fell on a Friday and neither one of us had work the next day. We again agreed to meet at the same swingers club. Jenna didn't know what she would wear up until the last moment. I told her that I would be dressed as a sexy blonde nun and to look for me.

I had made a nun costume before. It was a long button up black dress with sheer black belle sleeves. I had the white collar which covered most of my upper chest. I wore a black latex, lace up corset on the outside of the outfit to make it naughty. I also had a black and white wimple for my head. It covered the back of my long, blonde hair but the front strands still framed my face. I wore sexy black fully fashion stockings with seams up the back and Cuban heels. Black pattern leather stiletto shoes with gold spike heels completed the outfit. To make it sexy, I unbuttoned the bottom of the dress from the hem up to the top of my thighs so that my stocking tops and garters would show when I walked or crossed my legs. I made sure to wear bright red slutty lipstick to make my plump lips look enticing.

After arriving at the club, I noticed Jenna at the bar. She had several people around her. She looked really hot. Jenna was dressed in a pink satin, truck stop diner's waitress costume. It was adorable and tiny. It really showed off her sexy bare legs. The hem barely covered her tight round ass. She even had the little white ankle socks and pink stiletto shoes. She was doing tequila shots that someone had bought her. She was surrounded by a Catwoman who was another cross dresser, a male vampire, a hot blonde policewoman with a huge rack, and some others that I fail to remember.

I made my way over to her and when she spotted me she embraced me with a drunken hug. I quickly caught up with a few shots myself. Jenna then pulled the busty blonde police woman over to her by the hand and said, "Honey, I would like you to meet Sister Mary-Margret. Sister Mary-Margret, this is my wife, Officer Angela."

I was surprised that Jenna brought along her wife. It was unexpected. Angela proved to be every bit as charming as Jenna. She seemed a bit shy which was odd because her costume was very revealing and sexy. The blue top was a halter and her very large boobs were spilling out of it. The little blue pleated skirt was micro size and she had black fishnets on her shapely legs. Angela was a real knockout. The three of us shared drinks and chatted. Most of the conversation was between Angela and myself as Jenna kept getting free shots from strangers. She drank them and would sometimes give a the patron a kiss. The vampire guy made out with her for a few minutes and was squeezing Jenna's ass. I tried to gleam a reaction from Angela. I was a bit jealous. I wondered how she must have felt.

Angela assured me that it was alright with her. So long as Jenna was up front and honest with her than she was cool with it. She told me that she knew all about the kiss that I shared with her husband from our first meeting. Instead of jealous feelings, she said that it excited her and she looked forward to witnessing a repeat performance. I was looking forward to it too but first I had to get Jenna away from her many admirers. Eventually, Jenna returned to Angela and myself who were becoming good friends.

I was sitting on a bar stool with my back to the bar and my legs crossed. My stocking clad leg was exposed up past the welt to show a bit of bare thigh. Angela was standing beside me. Jenna was standing in front of me. She heard her wife and me discussing the kiss. Jenna took a step forward and straddled my lap. I could feel her satin panty on my nylon covered leg. Jenna grabbed hold of my head and leaned forward. She said, "Your lips look delicious Sister." With that she licked her lips and pressed her saucy mouth against mine. She kissed me aggressively right away. Her mouth was open and her tongue was searching for mine. I responded to her kiss with passion. I put my hand around her neck and held her close to me and with my other hand I cupped her ass cheek through her tiny satin skirt. Jenna moaned into my mouth. She was obviously turned on by my response. My tongue touched hers inside of our lip lock. Jenna's body gyrated with pleasure as she kissed me. As she grinded on my thigh, I could feel her growing hardness through the satin panties. I let my hand reach up under her little skirt and grab hold of her sumptuous ass.

Meanwhile, I wondered what her wife was doing and thinking during our public exhibition. I could see her between us. She was petting Jenna's hair and her other hand glided along the back of mine. Angela's big breast was pressing up against the side of my arm. I reached around her waist to hang onto her. "Angela cooed, "You two look so beautiful. That's so hot!"

My kiss with Jenna was mind blowing. Our passion was heating us both up as we made out with abandon in front of the crowd of strangers. Jenna was forcefully humping my muscular thigh. Her erection had forced itself out of the confinement of her pink satin panties so that I could feel the hot, bare skin of her cock on my nylon covered leg. She bit my lip in her excitement. We broke our lip lock and I kissed the nape of Jenna's neck. She stuck her tongue into my ear. Angela could see that Jenna's cock was erect and out too. She kissed her husband on the cheek. I looked around and seen the large group of people surrounding us to watch our lewd display. I had never had an audience before. I whispered to Angela, "Maybe we should take this to a back room."

"What for, this so hot like this. I don't want to interrupt anything," Angela replied as she gave me a soft gentle kiss. As I sucked on Angela's lower lip, Jenna began softly kissing her cheek. Jenna grabbed hold of one of her wife's breasts and squeezed the soft flesh. Jenna tugged at Angela's halter top until her left boob popped out. Janna grabbed Angela away from my mouth and kissed her passionately. I felt Angela's exposed tit against my face. I turned and found her big pink nipple in front of me. I licked wet circles around it with my long wet tongue. I then took it into my mouth for a good suck. As I sucked on her big breast, Angela made out with Jenna. Jenna continued to hump my thigh. I lowered my hand to Angela's bum and began massaging the round cheek under her mini skirt. She was wearing a black thong underneath.

I could feel the warm, dampness in Angela's crotch. Her thigh was already wet. My other hand continued to explore Jenna's ass. I had found my way inside her panties and had one finger teasing her tight little back door. When my finger pressed up inside her bottom, Jenna stopped kissing her wife and pulled my face off of Angela's tit. Jenna planted her mouth back on mine and kissed me hard again. She moaned with ecstasy. She grinded and humped my leg harder and faster. Her tongue was down my throat. That inspired me to finger fuck her asshole faster. My other hand was busy massaging Angela's clit through her thin panty. Jenna's hips pumped faster and her red hot cock exploded in orgasm all over my leg.

From our action my dress had ridden up to my hips. My upper thighs were on display as were my silky black panties. I had grown a stiff erection myself from my actions with Jenna and Angela. Jenna's hot semen was sprayed all over my bare thigh and the top of my stocking welt. Some had splashed my black panties. As Jenna slowed down her humping, she broke our kiss to catch her breath. As she leaned back, the evidence of her orgasm was exposed for all the on lookers to see. I reached down and squeezed out the last drops of cum from Jenna's cock. I raised my fingers to my lips and greedily sucked them clean. Jenna watched me and was turned on by it. She kissed me hard again and we shared her tasty cum between us.

Angela was excited by it too. I could feel my fingers getting soaked by her overflowing love juices. Angela pulled Jenna's face to hers so that she get a taste too. As the two of them kissed, I returned to Angela's inviting breast for another taste. Jenna's cum was still dripping down my leg and reaching the bar stool. Angela finished her kiss with Jenna and instructed her husband to clean up the mess that she made. Obediently, Jenna detached herself from my leg and bent down to my crotch. That made me remove my finger from her bum. Jenna began licking up her hot cum from my nylons and thighs. She sucked it all up while smiling and putting on a lewd show. I parted my legs so that she could get in between them. Her tongue swirled around my thighs and licked along the surface of my panties. I could feel her tongue through the thin material. She outlined my thick erection.

As I licked Angela's breast and fingered her moist pussy, she ordered her husband, "Jenna, be a good girl and suck off Sister Mary-Margret." Jenna hooked the side of panties with her finger until my trapped penis sprung free into the open. I had never been that exposed in public before. I could see all the on lookers staring at my thick, needy cock. It took no time for it to disappear again. Jenna took it into her mouth in one big gulp. She sucked hard on the meaty head. I muffled my moan into Angela's cleavage. My fingers jammed up inside her pussy up to my knuckles. Jenna's tongue worked my shaft. She licked down to my balls and sucked them one at a time. Her tongue worked its way back up my shaft to the head before taking another big suck deep into her throat.

I fought the urge to come right away. Jenna's mouth was making it difficult on me. I looked out at the crowd of on lookers. There were so many of them. They were encouraging the action by clapping, cheering and whistling. The vampire guy was rubbing Jenna's ass as she sucked my stiff cock. I had my hand in her red curls, encouraging her mouth. I opened my mouth to Angela's tit again and nursed on her finger like nipple. After a few minutes of that, Angela pulled my face to hers again and we softly made out as her husband sucked me off. I was in a zone. It was beautiful.

Angela stopped our kiss for a moment. She pulled a condom out of her purse and suggested to me, "Would like to bend Jenna over and fuck her in the ass?" Jenna was licking my shaft at the moment. I pulled her by the hair up to my face. I planted a long soul kiss on her mouth.. I sucked on her greedy tongue that was just licking my cock.

I parted from our lip lock and said. "Angela, I want you to sit on the bar here. Jenna, You are going to eat your wife's pussy while I fuck you from behind." I said with authority. Angela, in her sexy cop outfit, snapped a salute and hopped up on the bar. She sat at the edge with her knees parted. Her soaking wet black panties were visible to the whole crowd. Her one tit was still hanging out of her blue halter top. I got up from my stool and stood on the floor. My knees were a bit wobbly but I stayed perched on my five inch stilettos. My angry, almost purple erection was sticking out lewdly from the front of my unbuttoned habit. Jenna slid forward and bent her face to her wife's waiting crotch. Jenna pulled the panties to the side and immediately latched onto Angela's clit.

I went around behind Jenna, who was wiggling her sassy little butt at me. I flipped up her pink skirt and pulled her pink panties down to her mid thighs. The crowd cheered at the naked display. Jenna's cock was already hard again in anticipation. I lowered my face to her smooth ass and the crowd cheered again as I shoved my long tongue right up her asshole. Jenna responded with a moan and reached back to pull my face in deeper. I rimmed her asshole out and made it all slippery and wet.

After making a meal out of Jenna's butt I stood up and took position behind her. She flinched a little I pressed the big, wide head of cock up against her back door. My rubber coated cock pressed in as I grabbed Jenna's hips and pulled her body back toward mine. She winced again as I broke through the tight muscle and glided deeper into her asshole. Angela muffled Jenna's moans by pressing her juicy vagina into her husband's face. I drove home until my smooth wet balls slapped against Jenna's. Jenna loosened up a little and began grinding her hips indicating that she was comfortable enough to fuck. I took hold of her hips and began thrusting in and out of sexy bum.

The club's bartender was sexy black woman named Clare who as equally as busty as Angela. Clare was dressed for the night as Cleopatra. She was enjoying the show too and with Angela sitting on her bar, Clare seized the opportunity and began kissing the hot blonde police woman and feeling her up. Angela accepted the flirtation and planted her mouth on Clare's. Clare worked her hands on Angela's breasts which were both out by then. The two women made out with passion as I fucked Jenna while she ate Angela's pussy. It was an amazing sight. The onlookers closed in and I felt a few hands caressing my hair and my bum. I could tell that one of them was the tall transvestite Catwoman. The other was likely the male vampire.

I continued to fuck harder and harder until I couldn't last any longer. Once I saw that Angela was coming on her husband's face, I let go and exploded in my own orgasm. The crowd around us erupted in applause. I took a moment to catch my breath and realized I was at the centre of all that attention. I disengaged and excused myself to go to the rest room. I cleaned up and refreshed myself. I then cleaned up my makeup to look presentable again. As I was leaving, the Catwoman met me at the door and handed me her card. She blew me a kiss and whispered, "Call me."

I returned to Jenna and Angela at the bar. We had one last drink. Angela said that they wanted to leave and get some food. It was close to closing time anyway. The three of left and went next door to the pizza joint. I don't think the older gentleman running the pizza place knew what hit him when the three of us walked in dressed like we were. Needless to say, we ate for free. Angela and Jenna told me that they had never done anything like that before. I admitted the same. They told me that I inspired them. I blushed at the compliment. They said that they had a lot to discuss together and to work out alone. They would be going home together and I would be going my way. They were grateful that I understood and thank me again for the crazy sex. I assured them that it was all my pleasure and we parted ways.

I sat down to write this because I was going through my purse and came across the business card of Catwoman. Maybe, I'll give her a call?

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by cdCindy103/02/17

can't wait for chapter 2 and more

This is one of the best stories on Literotica. It's exactly my fantasy. I'm a CD who sucks cock and gets fucked but my wife doesn't know. I would love to be like Jenna where my wife encourages my cross-dressingmore...

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