I had been seeing this woman through the summer. Her name was Bonnie. She had shoulder length black hair, blue eyes, curvy figure. She was coquettish as hell. We had done everything but fuck, as opportunities never presented for full sex. Halloween was coming and an invitation to a costume party. We were talking amongst friends and the subject of were we going and what to wear came up. She surprised me by asking what I thought of her going as something like a James Bond character, with full dress, boxers and all. I asked if that meant she expected me to follow suit. And one of my best friends volunteered I'd done that before. At thirteen I dressed as an old hooker with sagging breasts. But I wore shorts underneath. Not panties and that expectation was what I was hearing. Bonnie whispered in my ear that she would make sure I got laid that night if I did it. After everyone headed for home, I felt trapped. I told my friend Sam I didn't think I could do it even though I really wanted to get laid by Bonnie. He said he thought I could do it and his sister might help, she liked kinky stuff. I said if I did it. I didn't want the world to know it. He told me not to worry. We went to his sister's house to talk to her. She was divorced with two kids and an easy to remember, Sissy. Cute and bubbly, with a little extra weight though not really what I would call chubby. As soon as Sam asked her she was on board and excited to help. I already regretted asking. She said she had black garter belt and bra she could lend that would fit me perfect as I was slim. She also had shoes she was sure would fit. They had high heels but they were block heels not stiletto. I would understand later. I would need to buy black panties that I would be comfortable in and she would do make-up. And she had a wig. Damn she must have had a premonition I was coming. I looked at Sam and he just grinned at me and said, "See."
I guess I was set to get laid. I went to Goodwill. Sam and I headed out to find something to wear with Sam's girlfriend Sue for feminine perspective. We walked in to Goodwill and Sue went right to the women's section an picked out a suit. A grey plaid pleated skirt with a red jacket, Blazer, whatever. She held it against me and it hit me mid thigh.
Sue smiled and said, "Perfect, That's why you brought me."
I tried on the jacket. It seemed to fit. No way was I going to a dressing room with all the eyeballs on me already. I paid and beat it out of there. We stopped at a women's clothing store where Sue like to shop. She found a pair of black stretch nylon panties that "I'd look cute in".
Then to Sissy's to leave my costume there. Sissy insisted I try it on for fit. I reluctantly changed and the girl declared a perfect fit. So now I had assembled the outfit I waited for my introduction as a woman.
On the afternoon of the party I went to Sissy's to get ready. She said Sam said he would be there after he and Sue had gotten ready. Sissy had sent her kids to Grandma's so there would be no distractions. I went with to her bedroom and undressed. Sissy took one look and asked why I hadn't shaved. I rubbed my neck and insisted I had. She rubbed my legs and corrected my focus. So, to the bathroom as she shaved me. It feels funny not having hair on your legs. I went to the bedroom and picked up the panties. Sissy giggled and told me she would teach me how ladies got dressed. She picked up the garter belt. I was standing naked as a new born looking at a mass of straps. She walked over to me and reached around my waist hooking the garter belt. She stretch the garters out and "Ole Woody" stood up too see what was a foot embarrassing the hell out of me. Sissy shook her head and picked up a stocking rolling it up on her fingers she asked which one. I stuck out my right leg and she knelt and began sliding it up my leg. The feel of the nylon stocking was totally unexpected, maybe it because my shaved leg was so smooth the nylon just glided up. Sissy had me stand as she stretched the stocking up and hitched it to the garters. They went further up my leg than I expected. I don't have a name or an explanation for the feeling of the nylon against my skin but I loved it. She sat me down and did the other leg. Now I was feeling it on both legs and my cock was so hard. I stood there and felt the "Fuck Me" feeling.
I heard Sissy ask, "So what do you think?" I couldn't answer.
She reach out, wrapped her fingers around my cock and said, "You've got to get rid of this before we go any farther."
I my mind locked up without a clue. Sissy lowered her mouth on it and began to suck. I heard myself say lets lay down together on the bed. I lay one way a Sissy the other. As she sucked I pushed the denim skirt she was wearing up and discovered she wasn't wearing panties. I buried my face in her pussy. It was wet and sweet smelling and tasted a little salty but delicious. As I flicked my tongue around her clit making sure not to make direct contact yet, she sucked me all the way to my balls and could feel her breath in my pubic hair. I licked madly up and down her slit probing her hole. Pushing my tongue deep int her, I think I might have believed for a moment I could lick her uterus. I damn sure tried anyway. I could hear her moaning and feel her hand trying to help direct me. I was trying to follow her leads and lick everything flicking my tongue quickly over every inch. I slipped a finger inside her and she pushed her pelvis at it firmly clamping her legs tightly around my hand so I could hardly move it. When she relaxed her grip I wend back to fingering her. Then I slipped a second finger in. I began concentrating on her clit flicking my tongue over it and getting a favorable response. Once again she clamped around my hand and put her hand on the back of my head making it difficult to get a breath. She started to relax and I started sucking gently on her clit. I heard her moan again,and she clamped everything down again. I was ready for her this time and took a deep breath first. Then she really started sucking her head bobbing up and down. I exploded filling her mouth as she swallowed every drop. But now I needed to wash my soaked and saturated face. I really liked Sam's sister. So now the dressing could proceed. I don't know if sexy was what I felt in those nylon stockings. But it still felt great.
Sissy then handed me the panties and said, "Now you can put the panties on."
And I asked, Are you going give me a blow job first before I put panties on every time ?"
Sissy said, "I'll do my best. "
I'm going be wearing panties from now on. I looked at the panties and they didn't look like they would fit me. I put one leg in each leg hole slowly slipped the panties up, stretching them out and letting them settle into place. And as I felt the nylon stretch over my ass and i felt the nylon on my cock and balls I thought to myself this is what makes them move that way and act so sexy. Feeling these against their bodies. I loved the feeling.
Next came the bra. Sissy put a couple of fillers that kind of looked like breasts and hooked it around me. It was anti-climactic after nylon stockings and panties. But I did look more feminine. And then on to the make up. Sissy cautioned me not to move as she carefully applied eye shadow, lipstick, and mascara. Then She paused a moment to admire her work before putting a cap over my head and secured it with bobby pins.I asked what that was, she said for this.Reaching behind her to remove the lid of a tall round box. Reaching in she returned with hair. A wig that she set carefully and began to comb and brush moving hairs this way and that. When done it settled between my ears and shoulders. Sissy handed me the blouse to put on then the skirt. As I stepped into the skirt raising it into place Sissy helped to button, zip and square me. She directed me to a full length mirror. There before me appeared my slightly homely twin sister, if I had one. I was really surprised at the result. I would never have imagined. So I turned one way, then the other, I reached down and felt the garter clasps at the second knuckle of my middle finger when standing upright. Turning to see the rear the skirt it fit comfortably, was about mid thigh.
Sissy said, "You have great legs."
With every movement the stockings and panties teased as I shifted brushing the inside of the skirt and keeping me semi-erect. You may want to think only pure thoughts if you don't want a wet spot on the front of your skirt.
"You know?" I asked.
She said, "I dress like this often, you'll get use to it."
I stepped into the living room to the appraisal of Sam and Sue. They both stood up smiling wide eyed and declared me fit for the role. Everyone was now ready so we headed out.
October is a cool month so leading up to Halloween it can be cold. Sitting in the back seat of Sam's car in Nylon panties and stockings I became more aware of that than before. Nylon does not insulate from anything. I was wishing there was such a thing as flannel panties and I'd considered those. when we got to where the party was there weren't many people there yet. I went looking for Bonnie and she wasn't there. I saw one her friends and went to ask if Bonnie had arrived or did she know when she would arrive. As I approached I got an indication of the answer. She started looking for an escape route as I asked about Bonnie and was told she wasn't sure. They came together and she should be around somewhere. And then i thought she cringed. Just a bit. So I began my search. I hoped I hadn't gotten all dolled up for nothing wondering how many women had had that thought in similar situations. Then I reached down and checked myself, just to make sure Sissy wasn't a witch and I'd been converted. The equipment was safely stowed, but Bonnie was absent. I went into a family room where everyone seemed to have gathered. I sat down reminding myself knees together and waited for Bonnie. I waited for some time as I talked to others around me. I was at a party so I needed to socialize. After a couple of hours I got up to walk off some nervousness.There was a small group in another common room listening to two guys playing guitars. As I stood listening I was bumped by an unfamiliar woman who excused herself and gave me her name which I've already forgotten. I gave her mine and told her I was looking for Bonnie. She started laughing telling me how foolish Bonnie had left as soon she'd arrived to go to another party thinking she could bed some college hunk she was hot for who was home for the weekend and surrounded by babes. I told her I didn't know him. She told me if I did I'd laughing at her too. Well that made me feel like a fool. As I wandered off she followed me and asked if I'd been there before since I didn't look familiar. I told her no I was invited by Bonnie. She said she was sorry, asked if I minded some company and I said sure. She told me I made a convincing girl as long as I didn't say anything. I thanked her and she offered to show me around. It was a big house with many rooms full of partiers. And we talked about where we lived, who we knew, and what we liked to do. We came to the end of a hallway and she said she was going to show me a special place. We went outside and across a concrete pad. A driveway, patio or something. And some distance from the house a building she said was a barn but the owners turned it into a multi-car garage with offices and rooms upstairs. We went up a long staircase to a hallway, to another room about the size of a hotel room and furnished the same way.
"Now this is where you come to party.", She said.
And then she asked if I would like to party. She said she always wanted to know what it was like to be with a woman and that I might be the safest bet. I guess cause I was hurt and angry with Bonnie I barely considered before saying yes. We kissed and she walked me over to the bed. As we settled we began caressing each other. It felt like we were moving faster than normal as I unbuttoned her blouse. She was satisfied touching me through my blouse. She wasn't wearing a bra so I began to softly kiss her breasts and tease her nipples with my tongue. She arched her back and pulled me tight against her breasts. I sucked one deeply into my mouth and flicked my tongue over her nipples as I sucked her breast and fondled the other breast rolling the nipple between my thumb and finger, pulling on it. She pushed my skirt up and then began softly rubbing my cock through the panties. The sensation through the nylon panties intensified my already inflated erection. She stood up and dropped her skirt to the floor, so I did the same. Then she removed my blouse. She was naked and I was in bra panties and stockings. She looked me up and down, smiled and said I'm digging this. She pulled me back onto the bed, we stretched out, she kissed me deeply and asked if I was hungry. She flipped and pulled my panties off slinging them. She wrapped her lips around the end of my cock. I kissed her softly over her mound, when i came to her slit I ran my tongue up and down it. Finding the inner labia already peeking out I teased it with my tongue. I flicked my tongue over the lips quickly and she responded by raising her pelvis up almost as if presenting it to me and i accepted and gently dipped deeper trying to allow her vagina to open up naturally. But she was pressing more firmly and my face ended up buried in her. She smelled so intoxicating. I softly sucked over her lips drawing them into my mouth, teasing her by pulling at them with my lips. As she sucked my cock deeper into her mouth I could feel it brushing the opening of her throat and the suction as she teased at swallowing me. I began flicking very quickly over her small lips and clitoris as she wet a finger so she could slip it in my anus and massage my prostate. I slipped a finger in her pussy making come hither motions. We seemed to be in a battle to make the other cum first. By the sound of her moans I felt confident. When I slipped a second finger in I felt her press back onto them. Then she clamped down and shuddered as I felt her juices run down my hand. She sucked me into her throat and I felt the muscles squeeze around my cock. It was like receiving a blow job and a tight pussy inside with strong muscles that squeezed a nut out of me. It was very effective as i unloaded washing her throat with cum. I wasn't sure I could stop until she withdrew my cock from her throat and sucked the remainder of cum from my cock.
After I finished she looked at me and said, " I guess you won, I came first, huh."
And then smiled ear to ear.
I answered, "Right."
We cleaned up as I washed my face and dressed up my make up. So she walked me back before we separated at the main party area. I looked around for Bonnie and then, not seeing her I found a place to sit down, I was glad it was nearing the end of the night. It's hard remembering to keep your knees together. so I got up figuring standing was better. There was a bar like the active wet bar along an outside wall. This was along an inside wall to the right of the other. I couldn't see any fixtures but the lights were out behind it and it was dark. I leaned on the bar not caring if it wasn't ladylike. A man walked up and leaned on the bar next to me. He was well into middle age, wearing a gladiator suit putting him as much in the elements as me and introduced himself as Richard but my friends call me. I was waiting for him to say "Big Dick", but he said Ricky. I gave him my name expecting him to leave once he heard my voice, but he stayed. We stood quietly for a moment then he leaned into me and said, " Some place, huh."
I agreed with him and he began telling me what a place like this would cost. Then i felt a hand reach under my skirt and stroke the back of my thigh. I looked him in the eye and he smiled back at me. He kept talking and slid his hand up to my ass. I felt him squeeze it, then cupping it rub his finger up and down along the crack. As his hand slid down I thought he'd stop when he got to my nuts. But he kept talking and rubbed his finger over them and then back up.
Then he said, "If you're up to it, let's go someplace a little more remote."
I thought a moment and then said why not. I came for sex may as well get some. I looked at him, smiled and said I know just the place. We walked over to the barn/garage and right up to the room I had recently visited as empty as we'd left it. Ricky wasted no time asking if I felt like I could give him a blow job. His directness surprised me but we were already here. So I said sure why not I'm dressed for it. He removed the bottom part of his uniform and sat on the foot of the bed erect. I knelt between his legs and started stroking his cock feeling the smooth firmness. He was a little bigger than six inches, maybe seven or eight. Not thick and the foreskin sliding back and forth showed he was uncircumcised. I bent down and licked the head running my tongue around it before closing my mouth around the end of it. I slowly took it into my mouth and began sucking about half way in before withdrawing to the glans. I slowly took as much of it as i could to see if I could take all of it. I couldn't, as the head reached the back of my mouth about an inch or so was left out. So I covered it with a couple of fingers and began sucking in and out. I rubbed between his legs to his anus, then wetting my fingers i fingered his ass. My fingers slipped in and I heard him say no so I withdrew it. He tapped me on the shoulder and when I looked up he was shaking his head.
"I sorry, I'm just not feeling it," he said.
His cock was still firm as I took it out of my mouth.
Then he said , "How about I suck you first to get me in the mood?"
I told him I was good for that, I would never turn down a blow job. So I stood at the foot of the bed as he removed my skirt and panties placing them neatly on a chair. I sat on the foot of the bed. He reached for my cock, I was hard and he stretched it and began stroking it. Then he knelt between my legs and stroking one nylon covered leg He began to suck me. He lingered on head head for a moment then sucked the length into his mouth. He withdrew and spit on his fingers, which looked like he had gotten some of his precum on them and pressed his fingers to my anus. Rubbing the hole and the spitting on his finger again slipped it in. He took me into his mouth. Sucking me deeply into his mouth until I felt his nose in my pubic hair and his finger rubbing my prostate. I loved the feeling of his warm mouth and his tongue working and my cock. I was surprised to feel him add a second finger as he probed me. He was sucking me all the way into his mouth and burying his fingers to the knuckles at the same time. The two together took little time to produce results as I flooded his mouth with cum. I had thrust up when I climaxed and now slowly settled on the bed. I felt something like Ricky was drooling just below my scrotum. I could feel it run down to my ass and collect on his two fingers still in my ass. About the time I figured out what was happening Ricky replaced his fingers with his hard cock.
He look up at me and said, "This is what would really feel good right now."
I just nodded as he pushed in. It wasn't thick but it was filling. I felt every inch as it slid in and it felt great as his pushed it to the hilt and pulled me to him kissing me on the mouth and inserting his tongue. I'm really not into kissing guys, it does nothing for me. But I can tolerate it when they have a nice cock in my ass. So I tolerated Ricky's kisses. I wondered if he was into fucking guys, or was he fantasizing I was a girl with a big outie. Well either way he was sure driving a hard bargain. He was driving into me with some force. I was enjoying it so much it was easy to forget the wet sloppy kisses. As he pounded I could feel a pressure building slowly deep in my balls. I did what i could to keep it on me and it blew all over my chest between the false breasts and everything finishing on my stomach. It took Ricky a little longer before I felt him filling me with cum. Afterward he continued to drive slowly like he was expecting a second wind. But it didn't come, so he gave me one more deep kiss. He looked at me and declared, "Damn, you were great."
I said, "Yeah, you were too, at least I got fucked tonight."
I guess i would have hated to get all dolled up like this for nothing. We cleaned up. Good thing they put a sink in here. I touched up my make up, don't want to go in looking used. When we got back to the main area everyone was leaving and Sue was looking for me. We walked out to the driveway and sue asked if I'd had fun since they hadn't seen me all night. I told her yes. As we stood there waiting for Sam, a car pulled in. Bonnie got out of the car and looked over at me with a sad disappointed look. She didn't walk towards me, she just stood there. Sam pulled up, I opened the door for Sue, She kissed me on the check and got in. I stepped to the back passenger door, looked at Bonnie, then as I got in I looked back as she quickly walked to the front door and went in. I got in Sam's care and we went back to Sissy's where I showered well. I was glad she had a hand held sprayer on her shower to get those intimate places. Bonnie and I have seen each other since , but never spoke about it. She gets real quiet around me and seems to prefer to avoid contact.
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written by peterpuller52