Crossing Over To Cross Dressing Ch 02

Crossing over to Cross-dressing

Chapter 2

So I left off after my Las Vegas trip, where my penchant for dressing was rekindled. I had connected with a couple professional Dommes again and I was seeing a woman professionally that to some degree became more than just a fee for service. She was mature, mid-forties, about 5’7” and 130lbs. She had super nice large breasts, 38Ds with big brown aureola and decent protruding nipples. She had long auburn hair and a small waist and legs and feet to die for, needless to say her ass was on par with the rest of her. She was genuinely kinky and not just going through the motions for the money. She lived in a secluded house near the water; perfect for coming and going discreetly. I saw her on a regular basis and we had many hot scenarios and some just routine spanking and BDSM sessions. There were a few that stood out from the rest. I even became her errand boy, she would tell me she needed to run errands and I would come over and take her shopping, to the dry cleaners, beauty salon and motor vehicle department. I usually met her in the afternoon but she wanted me over one particular time in the evening, she told me to expect to be there awhile as she had plans.

So I show up to her place in the evening and we did a session where she was wearing leather pants and a leather vest/bustier. Her tits were hanging out of the vest and she looked better than usual. She was unusually aggressive this time and she seemed actually horny. I did not dress up this time, she had me tied to the bed and was smothering my face with her ass and pushing my face into her cleavage while talking dirty. It was different in that she seemed like she wanted to make me extra horny. She stripped off her skin tight leather pants, they were inside out and she put the crotch of the pants on my face pushing them right onto my nose. She said “go ahead and breathe in my scent bitch! That’s it lick the leather you fucking pervert.” I licked away with reckless abandon; I could definitely smell the scent of pussy mixed with the unmistakable smell of leather. My cock was rock hard but I was tied up so I could not stroke it. She pulled the pants off and was rummaging in her closet for a while and came back and straddled my face, put her pussy an inch from my mouth and taunted me, she said “ if you can reach it you can eat it.” With that I gave it everything I had to lurch forward and taste her, she had let me do it every once in a while when she was really horny, but try as I did she kept pulling away as I neared her. Eventually the strain was too much and I collapsed back down on the bed. She spun around and planted her ass right on my face. I did not wait for her to tell me to lick her ass, I just started licking, she laughed and said to me “You really must want a good spanking slave, don’t you?” I grunted and kept licking, drilling my tongue as deeply as I could into her tight little rosebud of and asshole. I figured she always spanked me anyway and I loved getting spanked so there was no reason to stop licking her ass. She eventually got up and went back to the closet. She eventually found what she was looking for, she was a super sexy hot Domme, but she was not organized at all so her spending time looking for things was not uncommon. She untied me and let me rest a bit. I had brought a few bottles of wine and a bottle of vodka as she instructed me to do, so she told me to go open a bottle and bring her a glass of wine and she said if I wanted one to make myself one too.

I went to the kitchen and poured two glasses, I took mine and gulped down the entire full glass like I was chugging a beer, then re-poured my glass. We sat on the bed and chatted for a few minutes and drank the wine. She asked me how much time I had, I told her I had as long as she wanted and that I could serve her overnight if she wanted me. She said “good, I may keep you for the night, but later the session will end, but you will still do what I tell you.” I said “yes mistress.” She said that she had two special surprises for me that evening, one was something she knew I loved and the other she was not going to tell me. With that we finished the wine and she said to go clean the glasses and make me a vodka and tonic. I had made her drinks before so I knew how she liked them, strong with lime and ice. I helped myself to another glass of wine quickly while I made her drink. When I brought the drink back into the bedroom, she was standing there with a black leather bra on and a beautiful black strap on with a black leather harness. She motioned for me to come to her, which meant I got on my knees and walked on my knees to her. I handed her the drink and waited for her to tell me what to do, I wasn’t going to push my luck as I knew I still was due a spanking for licking her ass. She sipped the drink and said “perfect, I may have to bring you here to bar tend at my next party.” She sat on the edge of the bed and with her finger motioned me to her. I crawled over and knelt between her legs, this time I put my mouth a millimeter from the tip of the black cock strapped between her legs and opened my mouth. I waited for about 30 seconds but it seemed like forever, she put her hand on the back of my head and forced my mouth down onto the cock. She cooed “yes, that’s it, suck it suck it good bitch.” She knows I respond to dirty talk and uses it when she wants to get me going. The more she talked the more forcefully I sucked her cock. She pushed my head all the way down on her cock until I was deep throating her, she held my head down until I bucked and gagged. She released my head and I came up for air. She clapped her hands and said “bravo, I didn’t think you could do it, this is a big dildo, maybe someday I will make you suck a real cock, would you like that bitch?” I nodded and she said, “yeah, I know you would bitch.”

She made me lay on the bed chest down with my legs off the bed and my feet on the floor. She came up behind me and kicked my feet apart, spreading my legs and opening my ass. I felt the cold as she squeezed lube on my ass. The she positioned the head of her cock against my ass. The only time I was ever in control of a session for a few minutes was now, as trained, I would push back on her cock and I would control the initial entry into my ass. I had not played anally for a while so I was tight and it was slow going but once I got the full girth in me it went quicker. I slid my ass down the length of her shaft until it was all the way into my ass and the balls were pressed against my ass. I told her I was ready and that is where she took over again and it was me being hers again.

She stroked my ass and gradually increased the pace; occasionally she stopped to take a sip of her drink. She always talked dirty to me while she fucked me. She called me her bitch all the time and I loved it. She quickened the pace and was pounding my ass, she pushed hard and put the full weight of her body on top of me, her tits mashed into my back. She was whispering in my ear as she humped my ass she said “you are a good fucking dirty whore.” I told her I was about to cum as I was grinding my cock against the mattress as she fucked me. She said not to cum and she backed off her strokes and pulled out of my ass. She said something that I never forgot, “I think that is enough, a girl has got to mark her territory and you are marked as my slave, no one fucks this ass but me, got it bitch?” I said "yes Mistress."

She said it was time for the spanking and that it would be more severe since I took liberties with her ass. She got a paddle and a crop and made me get on all fours on the floor. She started with the paddle and I of course counted off the swats to my ass and thanked her after each one. She was hitting harder than usual and at a faster pace as well. She switched to the crop which is not good as it hurts way more than the paddle. Whack, whack, whack, three quick ones and I couldn’t even respond with the count or thank you. This might be worse than I thought. She continued to whack away and I made a vain attempt to count and thank but it was too much for me to handle. I started to actually cry and my knees buckled and I collapsed to the ground. She said that she didn’t want to hurt me but wanted to see how much I could take. She said that none of her other clients could even approach what she dished out to me. It was little consolation as my ass stung in pain.

I was prone to the floor for a while and she left the room. I got up and she heard me and came back in and she told me to get dressed. I stood up and she came up behind me and rubbed an ice cube over my stinging ass.

As I dressed she stripped completely naked and got dressed in regular attire. We ordered a bunch of Chinese food and went and picked it up. On the way back she said a friend of hers was coming over and we would all eat together. New twist, nothing like this ever happened before. Except once she was training a new Domme and I had the pleasure of being her first sub, but that is another good story for next time. This friend was not from the BDSM community.

She told me that her friend was going through some trying times and might come to live with her for a while and she was trying to figure out how she was going to conduct her BDSM activities with her living there. I was no help with suggestions, except to say just tell her and see how she reacts. She gave me more of the back ground of the woman, middle aged, in middle of a divorce, good looking but put on some weight, etc… Anyway, she shows up, she really wasn’t bad looking at all and well put together, beautiful face and big plump tits and a few extra pounds in the mid-section and ass and thighs, a diet and some exercise and she would be on verge of MILF status. She was wearing a dress with a floral print and showing some cleavage. We ate the food and drank the wine. She was interested in how the two of us knew each other. I was introduced as a friend, but she kept coming back to how we knew each other. I guess my dominatrix never mentioned my name to her and since they were friends she was wondering how she had never heard my name before. My Domme had once owned an antique shop in the trendy artsy area of town and I knew that so I said we first met when I moved to that area and was shopping for furniture and found her shop and we became friends. That quelled her curiosity for a while and we changed the subject.

We moved to the living room and continued to drink. I got up to pee and when I came back in the room they stopped talking, so I said "no fair, you can’t talk behind my back and then stop when I come back in the room, tell me what you were talking about.” My Domme said OK, we were talking about you. I said “OK what about me?” She said that “Joyce here thinks you are cute and that you have a nice butt, I told her that you would do a strip tease for us and she could see for herself.” I was starting to get drunk from the wine, so I sat on the couch right next to her friend Joyce and said that “I would but I left my thong and body oil at home.” Then I said the thing that changed the evening, I turned to my Domme and said “besides, you already marked my ass as your territory so it’s yours anyway, you can show it to anyone you want.” We all were succumbing to the effects of alcohol and we all laughed. My Domme looked at me with an evil grin and said “If I didn’t behave, she would spank me again.” That got Joyce’s attention and she cozied up to me put her arm around me and said “ohh this is getting interesting, you guys know each other better then you let on, tell me about his butt and it being yours.”

My Domme took a long drag on her cigarette and exhaled, the one thing I didn’t like about her was the smoking, and she laughed and said “ohh what the fuck Joyce, he is my slave, he does what I tell him to do and I sexually dominate him, that’s how I pay the bills” Joyce, looked at me and said “really?” Yes really she replied. So Joyce sits there for about a minute and then says “so if you told him to do a strip tease for me, he would really do it?” Yes, he would. “So what did he mean about marking your territory?” She looks at me and says “go ahead and tell her.” Without hesitation I said that before she got here that we had a session and during the session Mistress fucked me in the ass with a strap on dildo to mark her territory as hers and then she spanked my ass raw to finish the job.” I stood up and dropped my pants and pulled my underwear down and showed her my pink cheeks, then quickly pulled up my pants and sat down.

Joyce said “holy shit, that is so hot and kinky, I would never have expected to hear anything like that and the weird thing is I am really getting turned on by this.” My Domme then told me that Joyce has been in the middle of a divorce and hasn’t had sex for almost 2 years, “that’s actually what we were talking about when you went to the bathroom, how she hasn’t had a cock for so long and that she’d like to grab your ass if you weren’t mine.” I looked at her and grabbed my glass of wine and slugged it down and said I was willing to help out anyway I could. My Domme said, come with me, I followed her to the bedroom and she opened a draw and pulled out a leather thong and handed it to me and said be out here in a minute in this and put on a strip tease for her and make her feel like she is the hottest sexiest thing you have ever seen. I was stripping as fast as I could and almost fell over due to all the wine I drank and slipped on the black leather thong and came out into the living room and walked over to Joyce and started gyrating in front of her. I work out and at that time I was in pretty good shape, flat stomach and defined muscle on my legs and chest from riding and running but not a muscle guy, closer to a triathlete type body. But I was no dancer and improvised my way like a stripper, in any event, I was hotter looking then anything this woman had been around so to her I must have looked pretty good without sounding conceited I hope. I motioned to my thong and said tips are appreciated and she took out some bills from her purse and stuck them in my panties. I straddled her body as she sat on the couch and said let me thank you for the tip, I reached in and kissed her on the lips lightly and then I put my hand on the back of her head and pushed my tongue into her mouth and then sucked her tongue into my mouth and quickly released the kiss. She was breathing hard and flushed, but I persisted, I put my chest to her face and told he to kiss my nipple, “it makes me horny when they are kissed” She kisses tentatively and I push her head onto my nipple and said “sucking on them makes me even hornier.” She took the queue and sucked, and then I moved my chest so she could get the other nipple. Then I said “what makes me the horniest is if you bite them.” She started biting the one and I grabbed her hand and put it on the other nipple and I said “squeeze and pinch this one.” I started to moan in ecstasy. I grabbed her other hand and put it on my now bulging thong and motioned her hand up and down. She reached in and pulled the thong aside and stroked my cock. I said “hey that is going to require a bigger tip.” My Domme laughed and said “go to my room and take care of her, do anything she wants.” Joyce did not realize that when given an order, that I will immediately comply no questions asked and that this was exactly what I was really going to do. I got up and pulled her up off the couch and walked her to the bedroom.

Joyce said that I did not have to do this and don’t feel sorry for her pathetic situation of not having had sex for so long

I told her that even if I wasn’t instructed to do so, I would still love to be with her. I said “what will it be, sensual massage or raw uninhibited sex?” She said she hadn’t even used a vibrator in months and would love to let her hair down and fuck like a school girl. I stripped off her clothes and threw her on the bed and said “school girls love sucking cock under the bleachers” and I straddled her face and slipped my cock in her mouth, I started talking to her like she was a school girl, telling her how hot she looked in math class and gave her instructions like she never sucked a cock before, she initially wasn’t that good at it in actuality but I did tell her what to do and told her to grab my cock with her hand and stroke up and down while she sucked, suck harder, suck harder. She got the hang of it and I started talking dirty to her again and told her how fucking hot she was, the more filthy the language the more she sucked, my cock was throbbing as I had not earlier cum from the BDSM session, but my ass was still hurting and pink. I spun around and we settled in to a 69, I spread her legs wider than necessary to make her feel more like a slut. I kept telling her she was hot and sexy bitch, a horny fucking slut. She came a few times in my mouth and was soaking wet, moaning and screaming like she never had an orgasm. She was not trimmed and had quite a bit of hair and I pulled my face off her pussy and said, “school girls don’t have this much hair here” as I rubbed her pussy fur, “but that can be fixed.” I got up and went to the bathroom and grabbed the razor from the shower and warmed a wash cloth with hot soapy water. I rubbed her pussy down with hot soapy water and shaved the hair around her pussy lips and trimmed the top of her bush neatly. She just laid back and moaned the whole time. I told her that her pussy would feel good and she would never let her hair grow again once she felt how smooth and sexy a school girl’s pussy felt.

We jumped back in a 69 and I pumped my cock in her mouth like a piston. She had to come up for air and take arrest from my cock and she gained her breath and she said “fuck me now, fuck me good and hard right now, I want your cock in me right fucking now!” I turned around and pushed my cock in her pussy and it went right in, she was soaked with pussy juice, I was still hard and did not build up to a pace, I started fucking the shit out of her as hard and as fast as I could, thankfully the alcohol had a somewhat dampening effect that was holding off my explosion of cum. I think she was having one continuous orgasm or multiples I could not tell for sure but the whole time she was moaning and screaming and saying yes, yes, fuck me had keep fucking me hard, this is so good, I love getting fucked. The pent up sexual tension she must have had come flooding out. I told her that if she wanted to feel my cum inside her all she had to do was squeeze, pinch and twist my nipples. She did and in a matter of a minute or so I was shooting a big load of cum inside her pussy.

She was spent and just laid on her back, she moaned to me that she wanted to taste my come so I slithered up her chunky body stuck my cock in her mouth and said here taste this. She sucked on my cock as it became soft. I said to her “you like the taste of your pussy on my cock?” She kept sucking and nodded. I was not going to get hard again for a while or not at all so I pulled out and rested with her. She said she was hoping to get more of my cum to taste. I told her there was only one way to do that now. I slithered my way between her legs and put my mouth on her pussy and dug with my tongue and sucked my cum out of her pussy, I told her to squeeze her pussy walls and try to force out the juice and cum. I got a nice load of pussy juice and cum and held it in my mouth, my saliva was mixing with the pussy juice and cum to make it seem like there was more. I pressed my lips to hers and made her open her mouth and I slowly pushed the hot sticky mess of pussy juice and ejaculate into her mouth as we French kissed. Finally I pushed all of it in her mouth and pulled away from her. I told her to never tell anyone of the relationship between her friend and myself.