Popping Anal Cherries

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:)

2hr Massage Turned Into Anal Exploration

two different butt plugs
Image via Wikipedia

My second client of the day on Tuesday was a repeat client who I really like. He has way cute eyes! Anyway, I like seeing repeat clients because I already know a lot of their likes and dislikes. I already knew he was curious about anal. Last time he was in town he’d only hired me for an hour so I had just given him his massage on the bed and then we had our play time. This time he hired me for 2 hours and I had some real fun with him! I brought my table up to the room and after totally relaxing him with a back massage I started licking his ass. Then I got out my butt plug and after covering it with a condom I gently worked it into his ass. I massaged his glutes and the backs of his thighs while he tried to keep the plug in. It did pop out a couple times but it was fun for me to put it back in;)

I got my very small dildo and after putting the condom on and lubing it up I started to slide that in and out of him. He was arching his back so much I suggested he get on his knees and elbows to take it. Which he did. He was enjoying that so much I asked him if he could take more. He said he thought so. I got the next size larger and again after putting on the rubber and the lube I slid it in and out of him.

Finally, he couldn’t stand it anymore. He rolled on his back so he could grab my ass while I massaged his cock and used the dildo on his ass. We talked about him fucking me in the ass but before I know it I’d hit him in just the right spot and he came all over my hand and his belly!