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mrs. moneybags and her little faggot boy
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After our sex show ended, T and I walked back through the house. Our bodies were now cold from the exposure and our sweat, so we were given some large, soft thick towels to wrap our nakedness. We made our way back to the sitting room where we had left our suitcases so we could collect ourselves and discuss our next aspects of the evening.
‘She told me she wants me tonight,’ I said to T on arrival at the sitting room, hoping he would give me some pointers about her, but with no follow up forthcoming, I then asked, almost pleading, ‘What do I do with her?”
T looked at my silver metal suitcase. ‘Did you bring any of your prettyboy outfits?’ – ‘I recollected what I had packed. ‘Yes, the usual stuff I wore for you when we fucked… heels, the corset, I even brought my wig from the other night she saw me wear’.
‘Good. That’s what you wear then. I never dressed up for her, but I know she does like men who can dress like girls.’
I thought back to when I was on the stage and she called me a little faggot boy. The words stung me, but at this moment she was telling the truth. By how frequent she called me a faggot, I took it as perhaps her way of hinting what she wanted from me or what she was expecting.
Since the mansion was empty, and their two staff who saw us in our various states of undress while going to and from their theatre did not bat an eye, I decided I would show up at her door uncovered and exposed. I dug through my suitcase and pulled out my darkest black stockings, the corset, a little black silk collar for my neck, and my knee boots which I had squished in as a last minute addition.
As if my mind was being read, a minute or so after I had geared up, the butler appeared at the door of the sitting room. I stood up, my penis flopped down for him and the rest of the world to see, and took the handle of my suitcase to tow behind me. His blaise expression of business as usual at my appearance told me he had seen many others, like myself and T, come through this house.
‘I am ready for her’ I stated confidently, to which he then replied ‘follow me then’
He took me up the flight of stairs, stopped at the top, and point to one of the four doors in the hall way now in front of me. ‘That one there, at the end on the right,’ and then turned around and made his way back downstairs to wherever he kept his post.
I took a deep breath and made my way for the brown wood door. I knocked twice and waited.
‘Come in, dear.’
I walked into her large bedroom and looked around to get my bearings of the layout. Mrs. Moneybags was standing by the ensuite entrance, leaning up against the door frame. She had changed out of her green dress, and was now wearing a long, black, see-through negligee, black panties, and some open toed heels. I had not noticed it earlier when she was dressed, but she had rather large breasts, which were now showing. She had a drink in her hand, and took a long slow sip from it as she looked me over.
‘T was right when he said you looked good in women’s attire. He also told me that you like your women how you yourself dress up as a woman’. I just stood there but smiled at her words. She then walked over to one of her upright armoires, as she did so she kicked off her heels. She brought out some stay-up stockings and a pair of leather knee boots, more heel and pointy than mine were.
‘…so I’m going to look like you, then…’ she said, as she sat down on her bed and rolled up her stockings and stepped her feet into her boots. After zipping them, she then stood up as if to present herself to me.
‘Come here boy, don’t be shy. You and I are going to have lots of fun together, ’ she said, patting at the side of the bed next to her. Getting close to her, she opened her arms and put them around me, as I put mine around her body. I felt my aroused cock pushing against her, and her hands moved down my back to grab my ass cheeks, smacking it once.
I felt nervous inside, thinking that this sense of insecurity and vulnerability must be how female prostitutes must feel with clients they are unsure about – when they feel that their clients perhaps view them as sexual meat. I had felt that way with men, like Mister EU – but not so much when it came to women.
We stood there in embrace, looked at each other, she smiled at me, her eyes seeming to warm me up now …and then we kissed.
While I was thinking I would take things slow with her, right away her tongue was inside my mouth slurping around. I could hear and feel her breathing heavy in anticipation and arousal, as if she was short for time and wanted to make the most of me.
I felt her hand grope around between my legs and start tugging on my hard penis. She was running her fingers around me down there, exploring with her hand as we continued to kiss.
I then decided to take the lead, so I broke our lips apart – my mouth was now covered in her lipstick and spit – wiped my mouth off once with my hand, and then took her hand to lead her silently over to a wooden chair at the foot of her bed. I sat her down on the edge of the chair and then went down on my knees. I rolled off her panties and she immediately, instinctively opened her legs for me, as if she was presenting herself.
For an older woman who had some children, I was not quite sure how loose I would find her, but her long narrow slit was nice with a pair of juicy lips. She was soaking wet, probably had been aroused since our show for her. To make herself more inviting, she has scented herself with perfume. As I dived into her with my tongue, I lifted up both her legs up on to my shoulders. Right away I could hear her moan, and she began to slowly run her fingers though my hair – or rather, my wig – caressing my head in appreciation.
I kept going for some minutes. With the right woman, I loved eating them out and I had been told by numerous women that I was good with my tongue because I did not rush them to the next act. I just waited for Mrs. Moneybags to decide when she ready. Every once in a while, I would look up at her and try make eye contact, but she was always writhing her head back in pleasure.
Then at some point when I was back focused on her pussy, I heard her instructing me. ‘Boy, fuck me now boy’ she said as she moved her feet back down on to the ground. I stood up, held out both of my hands to help her stand up, and then took one them to lead her over to her bed.
‘How do you want it?’ I asked her. She replied with no words, just laying down on her bed and opening herself up to me. I climbed on top of her and immediately sunk my penis inside her. As I slowly pumped her, my attention was now taken by her big breasts flopping in rhythm to my thrusts. I grabbed both of them with my hands and massaged them as we fucked.
After a while, she pushed my hands aside and pulled me close to her. I started to pick up my speed and her breathing likewise increased. When I knew I was close to blowing my load in her, I kissed her and played her rough, how she seemed to like it, and stuck my tongue deep in her mouth. As soon as I could feel her trying to gasp for air, I let myself go inside her and broke mouth contact. She let out this long, loud deep moan, part in orgasm and part in exhaustion.
A minute or so later, after we had collapsed beside each other to regain our composure, she began to finger herself, licking our combined fluids off her fingers. She looked at me and held out her gooey hand, ‘you want any?’ – at which I just shook my head in disagreement. She gave me a shrug of ‘huh, your loss’.
Mrs. Moneybags then went for my now half-limp penis, putting her mouth on me so she could consume and lick clean whatever cum and pussy fluids were stuck to it.
As she sucked me, I felt myself becoming harder again, so I positioned her about so she was now on top of me in a 69 and I began to lick her. She interrupted what she was doing, asking ‘I thought you didn’t want any cum?’ before going back to work on me.
Licking her pussy from that reversed angle gave me view of her asshole, puckering and releasing every so often. I thought I would ask, ‘Can I finger your ass?’. – ‘No, you can’t go there’ was her curt reply.
‘So, can I lick your asshole, then?’ – she stopped and gave some thought, cautiously replying, ‘I suppose so’, in a tone that she was unsure completely of her response.
I began to gently rim her so she didn’t feel spooked out by something I could tell she had never experienced before. I then brought one of my hands into the act by fingering and massaging her pussy.
‘I said not to go in there!’ – ‘Don’t worry, no fingers’ I confirmed with her, as I simultaneously finger fucked her pussy and licked her asshole.
Rimming her that night is the last details I can recall from our first sexual tryst together, except we continued to fuck and suck and lick and repeat through until the morning. At some point as the sun was coming up, we both went off together to shower.
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Posted on : May 8, 2022
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Commented on May 8, 2022
Exciting! Sounds like a good time was had.
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