‘Debbie said that when I first started chatting to her,’ I teased.
‘Did she?’ Max asked a little concerned.
‘Not really, she was already shagging a guy she’d met on the Internet when I got in touch with her. I used to be at school with her and found her on Friends Reunited. I never really liked her much at school, she was always a bit prim and proper and I was more interested in girls that would suck my cock! We started off with email then Yahoo chat; just reminiscing about school and people we knew. One night she came on Yahoo quite late and she was obviously drunk. We started talking about sex and revealed our deepest secrets to each other.’
‘The one where you wanted your bottom shagging?’ Max laughed.
‘Actually it was her fantasy to dress in leather and bugger a bloke. She had seen a programme on Channel 4 about it and the idea turned her on. She had already got the fetish gear and the strap on because she runs Anne Summers parties for a living. Her husband wanted nothing to do with it though. He sounds like a bit of a knob to be honest; he’s more interested in football than his wife.’
‘Her confession made me realise that I’d love to have that done to me. At that point I wasn’t really playing with my bum when I wanked and my girlfriend at the time didn’t want anything to do with it.’
‘How long ago is this?’ Max said.
‘Four years since I first emailed her from Friends Reunited to say hi. We’ve been shagging for two years. I think we started talking about sex after a year or so of the odd email every couple of weeks and started chatting on Yahoo after 18 months when she gave up work to do the Anne Summers thing full time and bought herself a laptop. I guess she was lonely at home all day.’
‘So you offered your services?’ Max laughed.
‘I said I was willing to play with her if she was willing to cheat on her husband. That’s when I found out she was having an affair anyway. That guy didn’t like the idea of her being a dominatrix as he was quite dominant in bed himself. Then she had to come down here on business and I went to see her at her hotel. We drank quite a lot in the bar; just chatting about nothing really then she invited me up to her room. I told her to go up first and get changed then send me a text message. I had another pint while I waited. I remember I was sweating with nerves and my heart was beating really hard. The phone beeped and I almost cried out loud and spilt my beer!’ I laughed.
‘And?’ Max said excitedly.
‘I got the lift up to her room and knocked on the door. She opened it wearing a leather biker jacket, leather mini skirt, fishnets and calf length boots. She’s quite a small woman, I think she’s 5’3” and takes a size 10 dress but she looked a lot taller in the leather. She told me to come in and strip down to my underpants. I almost ripped my clothes off I was so eager. I got down to my underpants and she made me kneel on the floor in front of her.’
I stopped and took a drink of beer, excited remembering how sexy Debbie had looked in the leather and how I’d nearly cum in my pants with excitement!
‘Go on,’ Max said, obviously excited too.
‘She unzipped the jacket and let it fall to the ground. She was wearing a tight fitting PVC body suit underneath. It had covers over the boobs with poppers so you could expose them. Next she unzipped the mini skirt and pushed it down her body revealing the body suit had a popper cover over her fanny and the fishnets were tights. She was also wearing a harness with a vaculock fitting on it.’
‘Oh, I saw them on the web site!’ Max said.
‘She slowly turned around, letting me look at her but slapped my hands away when I tried to touch her. She reached into a bag on the bed and brought out a pair of leather handcuffs and tied my hands behind my back then rummaged around again and pulled out a dildo. It was fairly long and tapered to a slim tip. She fastened it on to the harness and posed with it. She’d hardly said a word since I’d walked in to the room and the tension was really erotic. She moved in front of me and grabbed my hair, forcing me to take the dildo into my mouth and suck it. She pushed it quite deep into my mouth and I choked a little but she didn’t stop fucking my mouth. Eventually she pulled it out and told me to get up and bend over the bed. I ended up face down on the bed with my arse in the air. My hands were still tied behind me remember so I was fairly helpless. She spanked my arse quite hard for a while then I felt something wet and cold dribble on my bum. She used her fingers to rub the lubricant over my arsehole and roughly pushed two fingers into me making me groan with pleasure.’
‘Did it hurt?’ Max asked her eyes wide.
‘Not at all thanks to the lube she’d just spread all over me. Her tiny fingers probably helped too thinking about it!’ I laughed.
‘Go on!’ Max said impatiently.
‘She finger fucked me for a couple of minutes, again not saying anything at all, then I felt her fingers withdraw and her legs pressing against mine. I remember the fishnets felt rough on my skin. I felt her guide the tip of the rubber cock to my arsehole, one hand pulling my arse cheeks apart so she could get in there. The slim tip pushed straight into me and she slowly pushed the entire length up my arse, not stopping until her hips were pushing hard against my bum. I remember letting out a long breath and moaning as I felt the dildo in my bum. It felt a hundred times better than a finger. Debbie raked her nails down my back and started to fuck me, pulling the dildo about half way out and then slamming it back into me hard and fast. My cock was rock hard and brushing against the bed as she fucked me and Debbie was breathing hard. I felt myself building up to cum even though I couldn’t touch my cock and whispered a warning to Debbie. She pulled the cock out of me and slapped my bum three times warning me that I was not allowed to cum until she told me to.’
‘Cool. I’ve always wanted to be able to do that!’ Max whispered.
‘She pulled me off the bed and turned me over so I was on my back with my bum at the edge of the bed. My cock was flat on my belly with precum leaking out of it. Debbie spread my legs and pushed the dildo back into my arse and started fucking me again. My hands were trapped underneath me and my cock was bouncing on my belly as she thrust into me. She pulled the covers off her boobs and started playing with her nipples as she watched my cock bouncing around. She must have fucked me like that for about five minutes, all the time I could see she was building up to an orgasm. Her face and neck were flushed and she was breathing hard. She was pulling her nipples and twisting them as she thrust into me.
Finally she cried out as she came and collapsed on top of me, her face just above my cock. The dildo slipped out of my arse with a wet plop sound and she slowly sank to her knees on the floor below me breathing hard. I managed to get up and knelt beside her asking if she was OK. She pushed me away from her and undid the handcuffs then led me to a chair and made me sit down. She undid the harness and dropped it to the floor then ripped the cover off her pussy revealing that the fishnet tights were crotch less. She straddled me and sank my cock into her cunt then fucked me hard and fast. She pushed my hands to her bum and kissed me, forcing her tongue into my mouth. I grabbed her bum, squeezing her cheeks through the PVC and forced her on to my cock as hard as I could. I didn’t last much longer than a minute before I shot my load inside her. She hoped off and lay back on the bed, demanding that I eat her out. I got between her legs and licked my cum from her cunt and made her cum again,’ I finished.
‘Wow, what a night!’ Max said, her neck flushed red with excitement.
‘That was just the start. We took it easy for an hour then she fucked me again with the dildo. This time she was naked and on top of me with my legs bent way back. She wanked me off while I bit her nipples. When her knees started hurting doing that I asked her to lie on her back and rode the dildo wanking myself off and cumming all over her tits. Once again she made me lick my own cum up.’
‘Had you tasted it before?’ Max asked suddenly.
‘Yes, I tried it when I first started wanking and I’d licked a couple of girls out after cumming in them.’ I admitted.
‘Was that it for the night then?’ Max asked.
‘Yes, we slept after that and then had a very nice shag first thing in the morning. That’s kind of been the pattern since then. We meet up, have a drink, and go to the room. Debbie dresses up and fucks me with a dildo in all kinds of positions. We make each other cum. In the morning we wake up together, shag for an hour or so then go our separate ways. The only time that was different was when I met her when I’d been to a meeting near where she lives. We went to her place and I lifted her skirt, ripped her knickers off, bent her over the kitchen table and fucked her as hard as I could. She was demanding that I fuck her harder so I poured olive oil over my cock and shoved it up her arse and made her scream!’ I grinned.
‘Jesus, that sounds brutal!’ Max said.
‘She loved it. It made her cum three times before I shot my load in her.’ I laughed, ‘I’m not a total shit. It was something we’d discussed doing when we were chatting on Yahoo. She’d had anal sex before when she was younger and never really got off on it and wanted to try it again. She also thought she would enjoy it more in a rape fantasy scenario so I fulfilled her fantasy,’ I said.
‘I can’t imagine Matt ever doing something like that. To him spontaneous means we leave the light on and do it on a weekday!’ Max smiled, ‘Do you think I need to have an affair?’
‘That’s not my choice and it wouldn’t be fair for me to tell you what to do. My longest relationship has been 5 months so I have no idea how to make a relationship work!’ I laughed.
We drank our drinks in a comfortable silence for a minute.
‘So what is the kinkiest thing you consider you’ve done?’ I asked Max.
‘Dressing up and masturbating in front of the mirror is fairly kinky isn’t it?’ Max replied.
‘With someone, not on your own.’ I teased, ‘Matt’s not your only lover is he?’
‘Not quite. I had two one night stands at Uni and went out with another guy for six months when I graduated. None of them were particularly kinky although Ben, the guy I went out with, did like it when I sat on him and played with my clit and boobs as I shagged him.’ Max said.
‘I need a wank!’ I said suddenly then realised I’d said it out loud.
‘So do I!’ Max laughed, ‘I wish I had my rabbit with me.’
‘There’s one in my bedroom!’ I answered.
‘Why?’ Max asked.
‘Joanne owns it,’ I clarified.
Max looked at me, her cheeks flushed, and appeared to reach a decision.
‘I’d like to borrow it please. Would you. Errm. Would you like to. I mean, if you want, would you like to watch,’ Max stuttered.
‘I would love to watch you.’ I smiled. I’d often fantasised about watching Max masturbate. Actually I’d often fantasised about doing all kinds of kinky things with Max!
Max was bright red and breathing hard with excitement and nerves but stood up and followed me into my bedroom. I opened the top drawer in my bedside cabinet and took out my toy collection. I had the rabbit vibrator, a long set of Thai beads, a stepped butt plug that starts off thin but gets thicker in graduations and a g-spot massager that I use when I have a wank as it works with body movement. You can stick it in and enjoy the sensations without having to contort yourself into a position where you can push it in and out. Finally I dropped a bottle of water based lube on the bed. Max looked at the toys on the bed nervously but didn’t move. I changed the lighting so the room was darker and put some music on.
‘Do you want me to leave?’ I asked when I realised Max was still standing looking at the bed.
‘No, I really want to do this. I just don’t know how to start!’ Max replied.
‘How about we take some clothing off?’ I said.
‘OK,’ Max said not moving.
I pulled my t-shirt over my head, undid my jeans and slid them off leaving me in my boxer shorts. I sat on the bed and tried not to stare at Max as she slowly undid her skirt and let it fall to the ground. She was wearing a black thong, black hold up stockings and still had her high heeled, knee length boots on.
‘You have lovely legs,’ I commented then added, ‘And a lovely bum!’ As Max bent over to pick her skirt off the floor.
Max smiled and pulled her top over her head revealing a matching black bra.
‘Should I leave my boots on?’ Max asked, ‘Is that kinky?’
‘God yes!’ I laughed, ‘I love a woman in stockings and boots!’
Max seemed to be relaxing a little now we were on the bed and semi naked. She lay back on the pillows and slowly ran her hands up and down her body. I was sat at the bottom of the bed with my back against the high baseboard watching her. I put my hand over my hard cock and rubbed it gently through my underpants.
‘Tell me about shagging Joanne. What does she like?’ Max said gently.
‘She’s very submissive and likes to be told what to do. Steve and I insist that she wears stockings and sexy shoes or boots on the nights we have threesomes and I insist that she wears stockings and boots when she comes over here. As soon as she walks through the door she takes all her clothes off except her stockings and boots and we come in here to play with each other,’ I said gently.
Max was relaxing now and beginning to get into what her hands were doing. I could see her nipples pressing against the semi-transparent material of her bra. My erection was getting painful in my underpants so I slowly pushed them down my thighs, pulled my legs out of them and kicked them on to the floor. I have a fairly big cock, not massive, but longer than average and quite thick. Steve and Joanne were quite impressed when they first saw me naked. Max opened her eyes and looked at my nakedness. Her eyes went wide at the sight!
‘Wow!’ She whispered, ‘You’re a lot bigger than Matt.’
‘Thank you!’ I smiled, gently stroking my cock.
‘Tell me more about Joanne,’ Max said undoing her bra and slipping it off to reveal a pair of small, pert boobs with very pink hard nipples.
‘She has bigger boobs than you and she’s a bit taller and fuller figured than you and Debbie. You have lovely nipples by the way,’ I said.
‘Thank you!’ answered Max looking down at them, ‘I’ve always liked them.’
I wrapped my fingers around my cock and began to slowly wank myself off watching Max play with her nipples with one hand and rub her pussy through her thong with the other. Max opened her legs slightly and her right boot touched my left foot. She rubbed it gently with the toe of her boot and smiled at me as she pushed her hand into her panties. I breathed out, totally unaware that I’d been holding my breath for the last few seconds after her boot touched me. I shuffled over on the bed so I was sat directly opposite Max, positioning my feet so I was touching her booted feet.
I could see Max’s hand moving away inside her knickers and began to wish that she’d take them off so I could see her pussy. Max has dark, auburn hair and I’ve always wondered what colour her pubic hair is. I couldn’t see it because of her hand and the thong in the way. I didn’t want to ask though as it might break the tension and excitement in the room. Eventually Max withdrew her hand and began to push her knickers down her thighs finally revealing her sparse, ginger pubic hair. Max leant forward and pulled her knickers off then piled my pillows behind her and lay back again, opening her legs and rubbing her booted feet on my feet and lower legs again. Her heels dug into me slightly as she did so and I yelped a bit in protest.
‘Did that hurt?’ Max asked grinning at me.
‘You did that on purpose!’ I said in mock outrage, ‘You bitch!’
‘I love it when you talk dirty to me!’ Max laughed, gently rubbing my legs again with her heels, ‘How does this work then?’
Max had picked up my g-spot massager. It’s a weird U shape with a bulbous dildo bit that goes up your bum, a bit that massages your perineum and a loop to enable you to pull it out. It’s hard to describe but once it’s in place you can lay on your back and kind of rock your pelvis and the dildo presses against your prostate and sends you into a massive orgasm.
‘You stick that bit up your bum, that bit presses under your balls and when you move the whole thing massages your g-spot and gives you a massive orgasm,’ I explained badly.
‘Show me,’ Max said sitting up and handing me it. I noticed she’d totally lost all her inhibitions now we were both naked.
I put a blob of lubricant on my fingers and knelt on the bed facing Max. I put my hands underneath me and found my anus then smeared the lube over the tight muscle.
‘Would you turn around so I can see please?’ Max asked quietly.
I smiled at her and turned around so I had my back to her. I bent over and slowly slid my lubricated finger into my own arsehole.
‘Oh my God!’ Max exclaimed with delight as she watched me finger fuck my own bum.
‘Good or bad?’ I asked looking back at her.
’Good. Wow, no, really good. Christ I never knew watching someone push a finger in their bum could be so sexy!’ Max said in a rush.
I poured a little more lube on the dildo and slowly pushed it into my arse as Max leaned forward to watch. I moaned involuntarily as it stretched me and filled me. Once it was in I turned around and sat back against the headboard, every movement making the dildo move inside me and making me shiver with pleasure. Max was still leaning forward watching me. I watched her small boobs wobble as she shuffled back into position and began to slowly wank myself off, moving my hips to press the dildo against my prostate.
‘You look really sexy in that outfit.’ I smiled.
Max smiled back and opened her legs to give me a good look at her cunt. Her boots slid along my legs again as she spread them wide and thrust her hips towards me giving me a quick, exciting, glimpse of her anus. I gripped my cock a little harder and stroked my foreskin up and down as I watched Max tease me. I opened my legs a little and shuffled down the bed so Max could see the dildo in my bum.
‘Oh god, that looks so sexy!’ Max sighed.
‘There are some anal beads there if you want to try,’ I offered.
‘Maybe later,’ Max replied picking up the rabbit and lying back on the bed, ‘This is all new for me so I’m going to stick with what I know.’
I nodded and watched Max push the vibrating dildo into her pussy. She was obviously soaking wet down there as the thick vibrator slid deep inside her first time. She put her head back and moaned loudly as the vibrating prongs of the rabbits “ears” found her clit and began to work their magic. Max used one hand to guide the vibrator about her clit, keeping it deep inside her, and the other hand stroked her body, sometimes stopping to pinch a nipple, sometimes rubbing her inner thigh, sometimes running through her hair as she fucked herself to orgasm with the vibrator. Her legs moved on the bed as she moved her hips in time to her thrusts with the dildo and her boots slid over my legs, sometimes digging me with the heels which sent stabs of pain and pleasure up my legs to my cock. I slowly wanked myself, shuddering a couple of times as the dildo in my bum gave me what I think of as small orgasms, but taking my time so I could watch Max.
‘Oh Christ!’ Max said throwing her head back and thrusting her hips off the bed as she reached orgasm.
‘Wow!’ I said softly as Max came for a second time, again thrusting her bum off the bed and giving me a lovely view of her clenched butt cheeks!
Max went limp and lay on the bed panting, pulling the dildo out of her pussy and dropping it on the bed next to her. I stroked her legs as far up as her knees with my feet as she slowly recovered from her orgasm. I was tempted to let myself cum but decided to wait and see what Max would do next. I wanted her to watch me cum. Actually, I wanted her to help me cum in various ways but wasn’t sure if she’d be comfortable with any of the suggestions I had!
Max lay on her back licking her lips and breathing heavily for another minute before she managed to pull herself upright again. I missed the feel of her leather boots on my feet as she got off the bed and headed for the loo. I wondered if she’d suddenly sobered up and was embarrassed. I was momentarily concerned for our friendship and my erection subsided. I reached between my legs and pulled the dildo out of my bum with a wet plop. I was just getting off the bed to check on Max when I heard the toilet flush and then Max was stood in the doorway again, still naked except for her stockings and boots.
‘Are you OK?’ I asked.
‘Yes, sorry about that. Sometimes when I masturbate and cum hard I really need to pee straight after!’ Max said, ‘I should have said something. Now I’ve ruined it for you!’
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<a href="https://www.lushstories.com/stories/masturbation/a-chat-with-maxine-part-2.aspx">A Chat With Maxine Part 2</a>