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Popping Anal Cherries

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Yesterday was extremely fulfilling. I had the opportunity to intorduce 2 gentlemen to the pleasures of anal stimulations (during seperate session though hehehe),

The first came to me. We got into the shower together. I soaped him up paying careful attention to his cock, balls and anus. We went into the massage room and I loosened him up with a therapeutic massage. I gently teased him as I worked at the top of each thigh, softly running my fingers up and down the crack of his ass and intermittently poking a finger tip in lubing up the the opening.

He was enjoying it so much I gently reminded him to relax down onto the table and take deep breaths. When I finished with the back side of his body I had him turn over. There I paid some gentle attention to his rock hard cock. He asked me if I had any toys and I replied “of course” and got out my starter dildo. The session became progressively kinkier as he was enjoying the toy and asked me if I could make it like I was fucking him with it. I sat on the massage table with his legs draped over mine and started to really rock his body. We also started talking dirty to each other about how kinky it was that I was fucking his ass with a dildo and how much he was liking it.

We switched back to my finger and as I finger fucked his ass with one hand I jacked him off with the other. I love feeling a guy cum on my finger!

The second cherry of the day was from a friendly gentleman who wanted some companionship and some power exchange. When I got to his room I instructed him to undress me, lick my nipples and sniff my pussy. I enjoy the sensation of breath on my wet pussy! Then I stood up and with him in front of me and gently caressed his entire front side and then backside through his clothes. Then I had him remove each piece of clothing. I stroked down his body again, lingering this time at his ass. I had him bend over and i got the lube and massaged his asshole. I instructed him to get up onto the bed on his hands and knees while I got a butt plug and covered it with a condom.

I stayed behind him and used the butt plug to work in the lube into his anus with one hand while gently stroking his cock and balls which were hanging below. I took some time but eventually his anus relaxed enough and I was able to push the anal plug all the way in. I directed him to lay on his stomach, pull his legs together to hold in the plug, and roll onto his back. I walked around so I was standing at his head and then climbed on top of him in the 69 position. I said now he could use his tongue and while he was licking away I started giving him a nice hot, wet blowjob.

He started to play with my ass so I grabbed the lube for him and he gently massaged and fingered my ass while he told me about another fantasy. When he was ready to cum I had him get behind me in doggy position and rub his cock up and down in between my ass cheeks until he blew his load all over my asshole. Then I made him lick it all up and spend some extra time licking my ass too.

After we recovered from that excitement we spent some time in the hot tub. He said he was tired and felt like calling it a night. I said that was fine but I just wanted to do one more thing (remember – he wanted to experience some power play). So I massaged his back and then lay behind him while he was still face down and went to work licking his ass. He was truly enjoying it. I jokingly asked him if he still felt like he was done for the night and of course he said no. I told him about how I wanted to take his anal cherry and use my strap on dilldo on him. Finally he turned over and nodded at me. I got on the harness and put the dildo in. He was laying on his back and was pretty flexible. He pulled his knees to his chest and I mounted him slipping my cock into his ass. I began fucking him slowly while he caressed my breasts. Toward the end I sped up and pumped his cock with my fist as I bounced up and down on the bed. This time he came on my cock:)

Cross Dressing Fantasy Appointment

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I am so grateful I like kink – it makes life much more interesting!

I had the opportunity to role play. His fantasy is to be be a woman who gets seduced by another woman. Guess who got to be the seductress!! I’ve had plenty of fantasies of seducing women so this was super fun to act out. He got dressed up and transformed into my friend who was coming over to go shopping. She knocked and I answered the door and the play began. We sat talking on the couch about where we would go shopping and I suggested some lingerie stores. I told her I had taken other girlfriends with me there. I was playing with her hair while we talked. As we began talking about lingerie I began running my fingers up and down her torso. I suggested we also go to a sex toy store as I put my hand up her skirt and check to see how wet she was. She was ready for more!

I guided her hand to touch my breast. I pulled my dress down exposing the nipple and guided her mouth to it. While her mouth was busy with my titties I pulled her hand down and up under my dress to feel my pussy. I was ready for more too! I asked if she had ever seen another woman’s pussy up close because I wanted to show her mine. She said no but she would like to see. I pulled the massage table close to the couch. I slipped off my underwear leaving on my high heels, thigh highs and garters. I sat on the edge of the table right in front of her, placed one foot on each side of her on the couch, lifted my dress so my pussy was right in front of her face. I began playing with myself, showing her the different parts of my pussy. She asked if she could touch. I took her hand and dipped her finger into the wettest part of my pussy then put it against my clit so she could explore. As she began to become more rythmic I had her switch and use her thumb… I like it better from the pad of the finger. She asked if I could eat her pussy. We switched places and with her sitting on the edge of the table I pulled her panties to the side and began working on her clit.

We moved to the bed. I asked her if she wanted me to fuck her woman to woman or man to woman since I had a strap on. She said she’d like to try the strap on if it wasn’t too big for her tight pussy. I took off my dress leaving on my shelf bra and thigh highs. I put on my harness and selected my smallest dildo to put the condom on and slide into place on the harness. I laid back and told her to show me how she blows her husband. It was very hot! Soon she was ready for me. First I took her bent over the edge of the bed. Then I took her doggy style on the bed. Last we did it missionary.

She asked if she could taste my pussy. Slipping off the strap on I said of course and I laid back as she got the dental dam and went to town on my pussy. She wanted to see me squirt. While I stayed on my back working my pussy she stood next to my head and I sucked on her clit. She couldn’t wait… She squirted all over my neck and chest!

Oh too much fun!

 

 

Make sure to let me know if you have special requests for your appointment – to act out a specific scenario, to wear certain clothing, etc. No, I do not think you’re gay if you like to cross dress – I think it’s kinky. And erotic. Just let me know – what is your attitude during a cross dressing experience? Are you a man enjoying the feel of the clothes? Or are you taking on a female persona for the moment as well?