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This was about 20 years ago. I was 19 and like a typical 19 year old I thought I knew everything. I was between jobs, still living at home and single. At this point in time I had had sex just a couple of times and was often looking for that next sexual partner.
My week was pretty basic. Grab a newspaper on Sunday for the job ads (this was spring 1999), call ads and set up interviews for later on in the week. Thursday declare defeat and spend Thursday and Friday online in various chatrooms. This was before online job hunting was the norm.
It was Thursday night and I was in my room on my computer in a chatroom. Sometimes I would pretend to be a lesbian and have cybersex with another lesbian who was probably also a dude, then if that didn’t get me off, find some porn and jerk off.
One night I was in a location chatroom for people in my area. I had been in a few here and there and quite often they would be a bust. Now my area is the entire Dallas/Ft Worth metroplex, so of course there was almost never a guarantee of meeting anyone within walking distance. I met a woman calling herself Ramona this one night. She sent me her pic with a paper with my screen name on it so I knew it was real. She was hot. Long dark, almost black hair. Blue eyes. Her cleavage showed that she had no less than a pair of Ds under her shirt. I showed her my pics and she was interested in me. She was clearly older, but that didn’t hurt my interest. The best part was that she was local to me.
I didn’t have a car so I was walking everywhere I went. Living with the parents meant that no one was coming over to pick me up or to make out in my twin sized bed. As soon as she mentioned that she was in my town my head instantly imagined me getting her top off and putting those nipples into my mouth.
We made plans to meet up the following night. She gave me her address, and we agreed to meet up around 9:30. I couldn’t think about anything that day other than being with Ramona that night. Around 8:30 I told my parents that I was going out and I hit the road.
She had a small house in the older part of town. You know those parts where the houses look like they are at least 60 years old. She was in one of those types of homes, but well kept. I nervously knocked on the door and she answered and instantly invited me in. I looked at the home, wasn’t sure what I was supposed to expect honestly. Some of the décor I thought was odd, but that was about it.
She was there. She was in blue jean shorts and a thin white top with her nips poking through. We talked for a bit. She commented on my nervousness and told me to calm down. I tried, I wasn’t successful. She leaned forward and kissed me. She tasted a bit different, but I couldn’t figure out just what had her different.
She broke off the kiss and suggested a movie. So we went to the movies and we both decided on one. She put it in and I returned to the couch. She left to get us some drinks. When she returned I started the movie and we drank and kissed and touched. The movie was just background noise honestly.
She laid me down and unfastened my shirt and kissed my chest. She undid my jeans and slid them off along with my boxers. I closed my eyes as I felt her give me the best blow job that I had ever had (at that point, I had only had three so it wasn’t much of a comparison). She knew what she was doing with her mouth. I warned her that if she continued that I was going to cum. She pulled out and removed her top. She came up to kiss me again and I did so, then kissed down to those tits that I had been wanting to play with all day.
It was better than I could have imagined. I was taking my time with them as I unfastened her shorts and pulled them down. I released her right nipple from my mouth to get a look at her in her panties and noticed the lump in her panties. She had a hard dick. I paused when I saw that.
She put her hand on the back of my head and guided me to her panties and pulled them down, releasing that dick. I gave in almost instantly and put it into my mouth and wrapped my lips around it.
I had come across pics of shemales before and I was curious, but honestly I never thought I’d meet one, let alone ever go down on one. I wanted to do to Ramona what she did it me. I could takes all of her, including her precum. I could feel the hard shaft under the soft skin.
We took turns sucking each other’s cocks. I had never done this before, but now I was enjoying it. We would take turns sucking each other, kiss, and return. She didn’t say a word and walked away for a bit, then she returned with condoms and lube.
I laid on the floor and she put the condom on me and lubed it up saying “You’re big enough that I’m not sure you’re going to fit.” and once she was done she straddled me and pushed my dick into her. We both moaned as I entered her. She bounced up and down on me. I could feel myself moving in and out of her tight hole and watched her boobs and dick bounce.
Finally she pulled herself up off of me and said “I need to get used to you.” I pulled her to me and kissed her Kurtköy Öğrenci Escort again. I could feel my hard dick against hers. I grasped hers and stroked it.
She grabbed one of the condoms and put it on as well as some lube. I watched her silently.
“I’m guessing this will be your first time?”
I nodded. She put her hands on my hips and said “Roll over.”
I did as I was told.
I felt her enter me. It felt good, then it hurt, then it really hurt and slowly it started to feel good again. I couldn’t keep my hand off my dick as she fucked me. She was getting faster and faster and getting more and more into it. I said “I’m going to cum.” and she said “Do it!” and I came on her floor. She went faster and pulled out. She rolled me over, pulled the condom off and came on my face.
Laying in my cum I pulled her to me and kissed her, smearing her cum onto her face and lips. We laid there for a bit before going to the bathroom to clean ourselves off. She asked me how that was, and I told her that it was one of the hotter experiences that I had had.
We saw each other a few more times, we were just having sex, nothing all that deep. When the subject came up from her about going outside, I got a bit nervous. And she realized what it was.
“Still in the closet I see.” She said.
“Yes.”
“I’m going to see if I can’t get out of it.”
I said “You can try.”
And she said “Okay.” and grabbed my hand and escorted me into her backyard.
It wasn’t cold or hot, just a late spring evening. She was in a nightgown, nothing more. I was just in my underwear. There was a wooden fence surrounding the yard, but her’s was the only house that was a single story.
“What are we doing out here?” I asked.
She laid back in the lounge near her back door. “You have a choice. The door is locked and I have the key in my hand. All your clothes are inside. You can either walk across town in your underwear, or you can get me to let you in.”
“And how do I do that?”
“Give me a blow job right here.”
“And those around us?”
“It’s after midnight, no one is looking out here. Who’s going to know?”
I was nervous. No one around us knew who I was, but still, my ego made me feel like if anyone saw me then they’d tell everyone in town and I’d be known as the guy who sucks dick. Still, I thought about it logically and slowly lowered myself down to the lounge next to her, lifted up her nightgown and proceeded to blow her. She didn’t cum, but she eventually gave in, and we went inside and fucked.
This began a new phase in our relationship. Doing things outside of her house knowing that we might get caught was part of it. One night we went out. She wanted to go to the adult store about 40 miles north, and go shopping. We were in her car since I didn’t have one, of course. She was in a skirt and panties as well as a blouse and bra. Sexy combination. She had me wear a bra and panties under my jeans and shirt. This was the first time that I had tried cross dressing and I was liking it.
It wasn’t long after we were on the freeway when she ordered me to give her a hand job. Something I did happily. When we were in the dark patches of the interstate between towns, I was instructed to lean over and suck her. There were other times during the trip that I was to undo my jeans and pull them down and rub the front of my panties. We were in a small station wagon, I know several people got a look at what I was and was not wearing.
When we got to the store, we kissed and got out of the car. Before we entered she stopped me and said “Not yet. You need to adjust your clothes.” I looked at her confused.
She came up to me, unfastened my shirt exposing the bra under it and pulled my pants down exposing the tops of my panties.
This was the first time I had ever gone inside of a sex shop and I wanted to walk around and look at everything…until I remembered how I was dressed. She and I weren’t alone in the store. Yeah, we were in a shop that wasn’t actually in a city, but had plenty of customers inside, even though it was 11pm on a Thursday. The woman behind the counter greeted us as we walked in and paid us no attention.
We walked around a bit. I was looking at the movies, people were looking at us…something I was very much aware of. She guided me to the gay section of the store. There, between the racks of gay videos she got more handsy with me. I closed my eyes to enjoy what was going on and when I opened them I noticed someone was coming towards us, another customer.
I tried to back away from her, but Ramona caught me and pulled me to her. The customer reached us and nodded at us. Ramona greeted him “Hi, I’m Mona. This is Anne.” She said, pointing to me.
“That doesn’t look like an ‘Anne’.” he said.
“No, but take out your dick…” Ramona whispered “And Anne here will show you why I him Anne.”
I looked at her, she couldn’t be serious. She whispered “Just give him a hand job sweetie.”
I said “We aren’t exactly alone.”
“It’s Kurtköy Çıtır Escort also a long walk home.”
He unzipped and we all stood real close to him and I wrapped my hand around his dick and began to pump. We were in a corner of the store in the gay area and Ramona was now behind me, dry humping me as I worked. I saw her also reach over and rub his ass.
He whispered “I’m about to cum.” and she pushed me closer to him. When he came it landed on my belly and the front of my pants and some in my hand. Ramona took my hand and licked up the cum and said “Good job Anne.”
We next went to the toy rack. She selected some lube and a butt plug. She paid for everything and we went to the car.
When we got to her place she said “That was so hot.” and we made out as soon as we got into her home. She pulled me to the bedroom, stripped me down and she entered me bareback for the first time and came inside of me, then rolled over and I fucked her bareback, cumming inside of her.
I closed my eyes for a bit after cumming. When I woke up she was dressed for bed and said “You need to leave soon.” I nodded in agreement.
She said “I have a few things for you, sweetie.”
“Alright.” I said.
She then handed me bras and panties. “Wear these when you come over from now on babe. Make sure they are cleaned.”
I took then in my hands and said “Yes.”
And she said “New rules, when you arrive, clean bras and panties or don’t come over.” I nodded and she said “Also, from now on, when I ask you to do something, anything, you do it. Question me again and we’re over.”
She said that with a tone that she had never used on me before. A tone that got my dick to leap straight up. She walked up to me, put her arms around me, kissed me deeply with tongue and said “Do you understand?”
I said “Yes.”
She said, “I wasn’t talking about your orders. I was asking if you understood that you are my…” she paused, “…cock sucking…” paused again and the next word was drawn out “bitch.”
That was so hot to me at that moment that all I could do was bend her over the bed, lift up her night shirt and push my hard dick into her ass and give her one more bareback fucking.
I showed up the following night at my usual time. I had on my typical jeans and shirt, with bra and panties under it. I was invited in and we chatted for a bit. She explained to me that she worked swing shift at a warehouse here in town doing HR and management stuff, the house was originally owned by her grandparents, and some other personal stuff. I explained that I was still looking for work, how being 19 and only having a high school diploma and no real job skills didn’t make job searching easy.
She told me to follow her and she led me to the bathroom. She told me to take off my shirt and jeans and to sit on the shower seat. I obeyed without question. She then proceeded to shave my legs.
Once that was done we went back to the bedroom. There was some clothes already laid out. She told me to pick out some clothes. I selected a knee length skirt and a matching blouse. She then gave me a wig to put on. She admired my looks. “I like the way you look tonight Anne.”
I said “Thank you.”
She smiled and pulled out some lube. She put some on her finger and then lifted up my skirt and slipped her finger in under my panties, applying it to my butthole directly.
I moaned in enjoyment.
She handed me a small purse and said “Here, take this and get into the car Anne.”
I took the purse and did as I was told.
The only thing she told me was that she had a surprise for me that night, but she wasn’t going to go into any detail on it. In the backseat was my regular jeans and shirt.
We drove that night into the big city. I rarely ever made it down here. We talked here and there about different things. We went to a hotel near the airport where we parked. We walked together from the parking lot to the hotel and I asked “If you have your own place, why did you rent a hotel room?”
She said “I didn’t rent it.”
Once inside the hotel we walked past the reception desk (both clerks eyed us funny) and to the elevators. I didn’t say anything, just followed along.
We got out on the third floor and went to one of the hotel rooms. She knocked on the door and announced that Ramona and Anne had arrived. The door opened and a woman in her mid 30s answered the door inviting us in. I could hear the shower running in the bathroom.
Ramona sat down on the bed and pointed to me. “How does Anne look?”
The woman walked around me and inspected me. “I think Anne will do. Young, tight I assume?”
Ramona smiled “Still tight.”
The woman said “Good.” and handed me a see though night gown that was purple and matching panties. “Put these on.” she ordered.
I looked at Ramona who said “What are you looking at me for?”
I took off all my clothes and put on the lingerie. The woman looked at me again and rubbed my legs. “Fresh.” she commented.
Ramona asked “Is Kurtköy Elit Escort Anne to your liking?”
The woman said “Yes, my husband will like Anne.”
I looked at Ramona who explained “For her husband, Crystal is giving him a birthday gift, you.”
Suddenly I got a little worried.
“Just do as you’re told Anne.” Crystal said and she stood up holding a belt. “Turn around.” she said and I did.
I felt the air on my ass as the back of my nightgown was lifted up and I felt the sting of the belt on my ass. “We aren’t going to tolerate anything less than you doing exactly what we want and expect.”
The shower stopped and Crystal said “Mona, are you going to stay or come back?”
“I’m going to leave.” She said standing up. She kissed me on the lips and said “I’ll be back when he’s done.”
Crystal laid the belt on the table and said “If you think I hit you hard, just piss off my husband.”
And with that, the two ladies left. And I stood there, waiting. Finally, the bathroom door opened and he walked out. He was a bit taller than me, older and fitter. He was completely naked. The lights had already been turned down low as the ladies left. I could still see the mighty dick, fully hard, on him, pointing towards me. I couldn’t think of a single word to say.
He pulled me towards him, kissed me and ran his hands up and down my back. “She out did herself this time.” he said.
I reached down and grabbed his dick and slowly stroked it. He pulled me away from it. “That’s not what I want.”
I whispered “What do you want?”
He didn’t answer. He turned me around and started to spank me bare handed. It was hard and it actually started to hurt. Then he picked up the belt and sat down on the bed. He pulled me down over his lap and proceeded to spank me.
I was yelping in pain. I didn’t ask to stop, but I was starting to tear up. He let go of me and said “That was what I was wanting, to spank some fagot in a dress.”
Somehow, even with my ass sore and tears on my cheek, that got my dick to throb. I looked at him and he said “You’re clothes are over there.” and pointed to the table where I left my clothes.
I was about to walk over to the table when there was a knock at the door. “Did someone hear us?” I thought.
He answered the door, completely naked. I looked and saw another guy at the door walking in. I didn’t say anything. He was wearing sweat pants and a pull over shirt. He came in, closed the door and pulled off his pants, showing another huge hard dick.
I didn’t move.
He came up to me, grabbed me and pushed me onto the bed. I felt my panties get pulled off of me and him pushing his dick into me. That dick was huge, I had never had anything that big inside of me, and it was bareback. Good thing I was already lubed, and from the feel of it, he was already lubed.
As this stranger forced his way into me, the first man stood in front of me and fed me his hard dick. As they both fucked me from different ends, I could hear them both insult and belittle me, and for some reason, I couldn’t keep my hand off my dick as it happened.
I don’t know how long we were like that, but when they came, the guy in my ass came in my ass and the one in my mouth pulled out and covered my face in it. I came long before that on the floor.
I had cum on my face and leaking out of my ass, and I hurt. They got dressed and left me in the dark hotel room on the floor.
I was there for probably about 10 minutes when the door opened up again. Crystal and Ramona walking in. Ramona came up to me and helped me up.
“Are you okay Anne honey?” She asked.
I nodded.
“Change clothes Anne baby, we need to leave.”
I stood up and removed my nightie. I walked to the bathroom and Ramona said “We don’t have time for that.”
So I walked back, removed the panties and put my panties, skirt, bra and top on. I picked up the lingerie to hand back to Crystal and Ramona stopped me. “You’re going to have to wash that and I’ll return it to her.”
I put my shoes back on and Ramona said “Aren’t you going to thank Crystal for the good time you had?”
I paused for a moment, then said “Thank you.” and Ramona escorted me out of the hotel room. It hurt to walk. When the elevator opened up on the ground floor I could see the hotel staff looking at me and knew exactly what was on my face and I didn’t care at this point.
It was close to 4 am when we got back into town. She said “I’m a bit tired and you look beat. I’m going to drop you off.”
I didn’t quite direct her to my place. There was a small park about two blocks from home. I told her there. She asked why, and I said that even though it was 4 am, I still couldn’t go home dressed as I was. She understood.
As soon as I got home I jumped into the shower.
By comparison, the next few weeks were uneventful. No strangers, no going out to stores, nothing public. But I could feel it, my spirit was broken. The insults continued and they turned me on. She had a spare room that she didn’t use in her house. The closet was full of clothes that she selected for me to wear when I came over. There was even a bed made up. The room was made to feel very feminine. Most of the clothes, she explained, were either old clothes that she never tossed out, or were picked from thrift stores dirt cheap.
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