A little about me I'm 45 and I have been dressing off and on for years now and have never had an encounter in person. I had only played with my toys and clothes. I finally got the desire to have a in person meeting after having recently broke up with my girlfriend after she didn't like the idea of pegging I brought up. I decided to go for it and had set up a weekend of enjoyment. I'm tall without my heels at 6'1" but have always been thinner for a guy my size.
I have collected a collection of clothes over the years ranging from lingerie and high heels to corsets and tight leather complete with cuffs, spreader bar and a few different gags. I even have a nice machine I use when I really want a good pounding. I'm sitting here in my room waiting for my first guest of the day the first of many this weekend. I have always had this fantasy of having multiple guys in one day all dressed up in clothes I had picked out for the weekend. I have been talking with a few guys and another crossdresser over the past few weeks getting the plan set and ready for the weekend I would come to San Francisco. I lived a few hours away and had the best luck contacting people there. I had set up the meetings this weekend to be completely worn out and satisfied after it was over while living out a few of my fantasies.
I had arrived at the hotel earlier and contacted my first guest Pam and told her I'd be ready to meet in a few hours. We had set up having rooms on the same floor of a hotel for the weekend and she would be my first and last guest of the weekend hopefully with one of her friend the last night I was in town. Pam and I have been talking off and on and found were both interested in the same things with her being more experienced and she was excited to help me explore the weekend and hopefully make this a regular visit. Once we were on the phone she said she would head over to her room and to let her know when I was ready.
I poured myself a nice stiff martini saving the wine for later and drew a hot bath. While the tub was filling I all nice and lubed up putting a generous amount inside me to be ready for Pam and slide the metal plug with a red heart jewel on it that and I had decided on. I slid into the hot bath and just soaked and enjoyed my martini thinking about what was to come. I shaved myself smooth because no self respecting lady has hair for there first date. I rinsed and dried off.
I had set out the outfit earlier for this evening and it consisted of a matching red bra, garter and panty set, with red fishnet stockings, patent red leather high heels, my black short dress, long red wig that hung down to my middle back in a long pony tail and my DD breast forms. I've always loved big breasts and decided that I should have a set too. I wrapped the corset around myself and tightened it up to give me the figure I wanted. I sat down and while finishing my martini I painted my toe nails bright red and attached a set of red finger nails I brought with me.
I applied my make-up and I've been getting faster at applying it but it still took me a little time for it to be prefect and finished it off with bright red lipstick to match my nails thinking I couldn't wait for my bright red lips to be wrapped around a nice hard cock and it would be happening soon.
I pulled up my panties, put on my garter belt and then rolled on my stockings attaching them to the garter belt. I attached my breast forms then put on my bra. I slid into my dress and put on my wig. Then slipped into my heels. Looking at myself in the mirror I was happy with what I saw hoping Pam would be too. I set by the desk in my room poured two glasses of wine and called Pam.
"Hi Pam its Ariel I'm ready for some company would you like to come over?"
"Hi Ariel I'll be over in a minute can't wait to see you."
We hung up and a few minutes later there was a knock at my door. I answered the door and let her in. We hugged and I stood back and took her in. She was standing as tall as me with a red braid over her left shoulder. After looking her up and down I said it was nice to finally meet you and you look good enough to eat.
Pam said "Oh you will get your chance."
We went out to the balcony with our wine had a cigarette and chatted about the weekend.
After we finished our wine Pam took my hand and drew me close. when we were face to face we slowly leaned in and kissed. It started out slowly at first then we moved against each other and embraced as our tongues slide together entwined. I felt her tongue inside my mouth and over my tongue. I slide my arms down around her beautiful ass and drew her close feeling her get hard up against me. She slide her lips and tongue down the side of my neck and hit my spot.
I leaned my head back and gasped took in a deep breath and said Pam I want to taste you. She leaned back and said what's stopping you? As she kept kissing my neck I used my hands and found the zipper to her black dress and slide it down then pealed her dress off her and dropped in it the ground next to us. I put my back to the railing as she removed my dress and tossed it by hers. I kissed my way down her chest and corset covered stomach stopping when kneeling in front of her.
"Do you want to move to the bedroom?" Pam said.
As I pulled down her panties and freed her beautiful cock I said "No I want you here and now."
I want to look to the city as you bend me over and slide into me. I looked at her cock seeing the head pointed straight at me. It was a nice 8" cock I estimated a bit bigger than mine. I reached up and wrapped my hands around the warm hard flesh and brought the head to my lips and kissed it. I spread my lips and stuck my tongue out and licked the head tasting the pre cum off the head. I looked up into her eyes as she watch me and spread my lips taking the head into my mouth as she watched my. I couldn't believe it I was tasting my first cock.
I loved it it felt soft and hard at the same time I sat there savoring the taste and running my tongue over the head while stroking my hand back and forth. Pam moaned in pleasure and reached down and stroked my hair. I started moving my head back and forth working more and more of her cock in my mouth. I took about four inches into my mouth and stopped while moving my tongue are her hard cock I reached down and massages her balls waiting for the present I was waiting to taste. I could just imagine what I looked like. A red haired woman kneeling taking a cock in my mouth while my lover watched me and the city at the same time.
Pam looked down at me and asked if I was ready to be the slut I wanted to this weekend. I couldn't talk with her cock in my mouth. While looking into her eyes I nodded my head yes while running my tongue over her cock. I reached around her ass and spread her cheeks apart I felt in between her cheeks and found the plug feeling the heart shaped head that matched mine. Pam reach down and grabbed the sides of my head and slowly started feeding more of her cock into my mouth.
I felt my bright red lips touch the bas of her cock I slide my finger into her finding her prostate and applied some slight pressure. Looking into my eyes Pam said that's the spot. holding onto the sides of my head she slide her cock out till I just had the head in my mouth. Holding my head in place Pam slide her cock all the way back into my mouth. Using my tongue as much as possible while she was sliding in and out of me. I could feel myself harder than I have ever felt myself before. As she was fucking my mouth I slide my hand down to my own cock and start to stroke it wanting to come when she did. Pam stopped with her cock all the way in my mouth and told me no.
"Ariel you can only cum with me in your ass or you in mine understand?" I nodded my head yes. "Now Ariel I'm close i want you to taste it when I cum and swallow it all."
I rolled my tongue around her cock in my mouth and she started sliding in and out again. Pam started to move faster in and out over and over her breath quickening. Pam said she close get ready. I just nodded and started sucking harder. She pulled out till just the head was still in my mouth and let out a loud moan and exploded in my mouth. I squeezed my lips tighter around her cock and felt her cum coating the inside of my mouth over and over. It tasted sweet and started to fill my mouth. I started to swallow while milking every last drop from her.
"Hold ,my cum in your mouth and enjoy it" Pam told me.
She filled up my mouth and I was moving her cum around my mouth with my tongue. I felt that she had stopped cumming in my mouth and I started to feel her begin to go soft.
"Looking into my eyes Pam said "No Ariel swallow my present."
I started to swallow and as I did she slide more of her cock into my mouth. As I swallowed her present I felt her stop going soft and start to harden again. She could see the look of surprise in my eyes and said oh yes Ariel there is no break for you once your done swallowing I'm going to bend you over and take you over the railing. I smiled and Pam started moving her cock in and out of my mouth again.
Once she was hard Pam was as good as her word she stood me up and bent me over the railing. Pam pulled my panties off ripping them in the process. Pam spread my ass cheeks apart revealing my plug.
"Oh Ariel your wore it just like mine."
"Of course I did sexy I wanted everything to match."
As Pam reached in to pull my plug out she asked "Ariel did you use the lube I suggested?"
"Strawberry just like you asked me to" I replied.
With that she removed my plug and I felt her run her tongue from my balls to my puckered anus and the slide her tongue into me. She I gasped in shock of how good it felt and she started to slowly tongue fuck me. She continued while I moaned in pleasure pushing my ass against her tongue trying to get it farther into me.
She pulled away from me a stood up putting her hard cock in between my cheeks and started rubbing back and forth squeezing me cheeks against her hard cock. I could feel the head of her cock brushing up against my tight puckered hole and couldn't take it anymore.
"Pam" I moan "Make me yours put it in me I cant wait anymore to for your take me."
"Ariel put me where you want me." Pam replied.
I reached between my legs and encircled Pam's cock with my hand. I placed the head of her cock by the desperately waiting ass pussy. That's how I thought of it now. I wanted Pam to make me her slut and fuck me till she filled me with her sweet cum. I didn't just put it at my entrance I started rubbing the head up and down between my cheeks teasing her. Figured turn about is fair play.
Pam playfully slapped my ass and said "Tease."
"Its only a tease Pam if I don't let you fuck me."
I wanted her hard cock in me no more teasing no more hesitation just her beautiful hard cock in me. I put the head of her cock at the entrance to my ass pussy and slowly started to push back onto her cock. Pam grabbed my hips and stopped me and I whined.
"Oh please Pam please stick in in me I want you inside me."
Holding my hips still Pam slowly push her cock into me. I felt the invasion of her into my body and wanted more. I wanted to impale myself onto her cock but I wanted to savor every inch entering me for the first time. I could tell Pam wanted me to feel every inch of her enter me so I let her. I felt the head pop in. I rolled my head back my my eyes closed feeling my braid fall over my right shoulder as I relished in the feeling of Pam sliding into me. Pam slowly slide her cock into me I could feel every amazing inch of her as my ass pussy greedily swallowed every inch of her. I could feel her pelvis push up against my ass and I enjoyed being completely filled by her.
Holding onto my hips Pam let me adjust to her. After a minute Pam started pulling out and as I could feel her pull out I tried to push myself back to keep her from pulling out. Pam's hand came down hard on my ass. I yelped in surprise and pain but stopped pushing back.
"Now Ariel I'm in control right now. There will be time for you to take over later if you try it again I'll give you a nice spanking for a reminder."
"Yes Mistress" I nodded my head and responded. Pam was taking control like I told her I wanted to try and I completely loved it.
After the words left my mouth I could feel her cock twitch inside of me. She hit my ass with her hand as a reminder. Pam continued to pull out till just the head was in and stopped. She put her hands on my shoulders and said now your mine. Without waiting for a response she shoved her cock all the way into me in one thrust. I groaned in surprise holding onto the railing for support. She didn't stop this time and kept thrusting in and out of me. She kept at it and my knees started to get a little weak and I could feel my hard clit bouncing and hitting my stomach with everyone of her thrusts. I started to squeeze my ass pussy every time Pam thrust into me and I heard he moan behind me.
"Oh Ariel you dirty little girl you never told me you could do that."
Pam buried herself in me one more time then pulled out. I turned around with a frown on my face disappointed that she had stopped I was so close. As I turned around I saw her sitting in the balcony chair stroking her hard cock.
Pam mentioned me over with a finger saying "Come on Ariel time for you to enjoy your ride."
I winked at her as I walked over to her. I bent over at the waist kissing the head of her as she was stroking her cock. I turned around and bent over at the waist showing her what she would be enjoying. Pam slapped me on the ass as I reached between my legs to take ahold of her cock to help guide myself onto her.
Holding onto her cock I lowered my ass and put her head just inside of me. Once the head was in I thrust myself down onto her impaling myself in one smooth motion. While holding onto the sides of the chair I started to bounce up and down. I shifted just a bit as I was bouncing and started to hit my prostate with ever thrust down. I started to move faster and faster. Pam moaned behind me reaching up and grabbing my left breast while wrapping her right had around my clit.
Every time I thrust off her cock she stroked my own. I was fucking myself from both sides at the same time and I was loving it. I could feel the pressure build up as I was about to explode. I lasted a couple of more thrusts. As I pushed down onto Pam I felt my toes curl and my legs start shaking. I cam all over myself while rocking back and forth on Pam. Pam stroked me milking out every last drop. As the last drop dripped of the tip Pam grabbed onto my hair and feed me her fingers no Ariel clean up your mess. I sucked very one of her fingers clean. I could still feel Pam nice and hard inside of me.
Still wanting to please her I stood up and took her hand and guided her into the bed room. Sitting on the edge of the bed I grabbed my bottle of strawberry lube and poured a generous amount all over her cock.
Looking into Pam's eyes as I stroked her hard cock she said "Now I'm going to fuck you and cum all over your face."
Pam stood me up and turned me around and grabbing a color with a chain attached to it off the dresser she put it around my neck. She put me in a kneeling position on the bed. While holding onto the chain she causing my back to arch she put her cock in me again and shoved it all the way in. I moaned in pleasure.
The was no stopping this time once she was all the way in. Pam started fucking me hard all the way in then all the way out. She pull my back to her and I could feel her breasts against my back. I could feel myself hard again she was hitting my prostate with every thrust and I could feel the warmth building in me into another orgasm. Pam forced me back into a kneeling position grabbing my hips with both hands and started fucking my faster. This lasted for about five more minutes and I couldn't take it anymore.
I wrapped my hand around my clity and started stroking myself to every thrust. I exploded all over the bed and could fell my ass pussy tighten around Pam and I could feel her grow getting ready to explode. Pam slammed into me one more time and I felt her first shot inside me and loved it. I she pulled out quickly as I knelt in front of her.
Pam came on my corset all the way up my chest and all over my face. Looking up at Pam I opened my mouth and stuck out my tongue and Pam grabbed my head and shoved her cock into my mouth and finished coating the inside of my mouth. I suck every last drop out of her then we both collapsed onto the bed. Pam licked her cum off my face them I lowered my head to finish cleaning her up.
Once finished we looked into each others eyes and I said "That was amazing thank you Pam. That was by far completely worth the wait."
Pam looked at me and said "That was amazing but I think well be able to top it Sunday afternoon."
Pam and I kissed and all I could think was I can't wait till Sunday.
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