‘Have you ever had your bum fingered?’ asked my flat mate Jill.

‘That’s an unusual conversation opener,’ I replied smiling and trying to sound casual even though my stomach had just turned inside out and I had the beginnings of an erection.

‘Steve asked me if I’d play with his bum and I just wanted to get some advice,’ Jill said, ‘and I wanted to see if you’d squirm.’

Jill and I had been sharing a flat for two years and I’d been in serious lust with her for most of that time. She was 5’ 6” of slim, brunette loveliness with no interest in me. The situation wasn’t helped by her habit of wandering around in her underwear or a towel and her frequent conversations about sex.

‘I’ve had several girls slip their fingers up there when they’ve been sucking me off,’ I admitted.

‘Several?’ Jill asked raising her eyebrows.

‘OK, two,’ I laughed thinking about the two ex-girlfriends in question, ‘Sarah used to do it frequently, Michelle did it once and didn’t like it enough to do it again.’

‘I take it you like it then?’

‘Yes, very much so. Just make sure your nails are not sharp and use some lube if you’re going deeper than your second knuckle!’ I exclaimed a little too loudly.

‘So how deep should I go? He says he’s never tried it before and I don’t want to freak him out.’

‘Second knuckle should be fine,’ I replied, wishing it was going to be my bum. I’d not had sex for six months now and it was starting to get to me.

Jill contemplated my advice for a minute or two then said,

‘So, tell me about the best anal play you've received. I want an example so I can do it right with Steve.’

‘It’s probably a tie between two different occasions. The most erotic time was with Michelle because I was naked and she was fully clothed. She was wearing a black button up dress, heels and black stockings. She’d been to a work function and was a little bit drunk and turned up just as I was getting out of the shower. She made me lie back on the bed, unbuttoned her dress down the front so I could see her underwear then started to suck me off.’

‘Nice,’ Jill smiled, ‘continue.’

‘I slipped my hand down between her legs and was going to slip a finger in her but she warned me it was the wrong time of the month. I made do with caressing her bum and running my fingers over her bum hole. I knew she liked me touching her there but wouldn’t let me penetrate her hole. She moaned whenever I touched her hole which was nice as her mouth vibrated on my cock. I guess I decided to chance my luck with her as she was drunk and started to concentrate on her anus. To my surprise she moved her hand down to my bum and started to do to me exactly what I was doing to her. She started to moan louder and her hand and mouth moved faster on my cock.’

Jill sat forward in her seat, listening intently as I continued,

‘I slipped the tip of my finger into her arse and felt her do the same to me. She pushed her bum back against my finger slipping more of it inside her. Her finger penetrated me deeper. I pushed harder and felt my finger go in up to the first knuckle with her finger following suit in my bum. I started to fuck her arse with my finger and she did the same to me. She came before me and her arse squeezed my finger. The sheer fucking hornyness of the situation made me shoot in her mouth.’

‘And you only did that the once?’ Jill asked in amazement.

‘Yep. She said she’d enjoyed it, it was a spur of the moment thing, but anal sex was dirty and she didn’t want to do it again. She dumped me for her husband to be just after that anyway. I often wonder if she finger fucks his arsehole,’ I said trying to look wistful and sad.

‘OK, what was the other time then?’ Jill demanded.

‘Oh yes, with Sarah. Now Sarah did like her bum touching. She especially loved being rimmed and fingered during foreplay and, as I’ve mentioned, she liked to shove her fingers up my bum.’

‘Fingers? Plural?’ Jill interrupted.

‘Yes, usually two but on occasions three. Obviously slowly and with lots of lube,’ I explained, finding myself getting off on the story. ‘If I was on my back and she was giving me a blow job she’d just use one finger but sometimes she liked me on all fours so she could finger fuck my arse and milk me.’

‘How the hell did she suggest that to you?’ Jill laughed.

‘She told me to get on all fours and just did it,’ I replied. ‘We tended to do that. The first time I fucked her anally I just told her to bend over the bed, I fucked her normally for a minute then lubed her arse, fingered her until she was loose then slipped my cock up there.’

‘Bloody hell, the first time I got my bum fucked it took a week of nearly doing it but stopping at the last minute, then nearly an hour of preparation before it finally slipped in!’ Jill exclaimed. ‘The guy I did it with had quite a small cock and we’d pushed so much lube in there I could barely feel him! I remember wondering what all the fuss was about. The next guy I did it with was hung and I found out that it can be painful and it’s fucking fantastic once the pain goes away.’

‘I’ve been with girls that took ages to go the whole way too but Sarah just liked to be spontaneous,’ I smiled, shifting position to get my erection comfortable before continuing, ‘Sarah got me on all fours and started rimming me as she milked my cock. That was the first time she’d rimmed me too and that would have been fairly cool on its own but she lubed me up and started inserting fingers in me until she was deep inside me with three fingers. She finger fucked me until I came all over the bed. It was the first really intense orgasm I ever had.’

‘I think I need to go and see Steve,’ Jill said, reaching for her mobile phone and heading towards her bedroom.

Five minutes later she called goodbye and the front door slammed shut. I was painfully erect and horny as hell. I practically ran into my bedroom and sat in front of the computer. Within minutes I was browsing through pictures of amateur women and stroking my cock. I love looking at ordinary women, especially when they’re wearing stockings and tights. My mind started wandering to Sarah. She always wore nylon for me when we fucked. At first she wore stockings, then as we got to know each other, she’d wear black crotch less tights or body stockings, encasing her soft, slightly chubby body in nylon for me to rub myself against. I came on my chest twisting my nipples and thinking about my thick cock sliding up Sarah’s tight arsehole and the feel of cool nylon pressing back against my thighs.

An hour or so later I was watching TV in the living room when I heard the front door open. Jill walked in with a wry smile on her face.

‘How did it go?’ I asked muting the TV.

‘Well he won’t want to do that again,’ she smiled, ‘I think I got a bit carried away and hurt him. Scared him a little too! It turns out that he doesn’t like taking anal as much as he likes to give it.’

‘Well at least he tried and you got laid,’ I laughed.

‘Actually I didn’t. He wasn’t in the mood once I’d violated his bum hole and I have to be here tomorrow morning, so I left. Did you have a nice wank after I left?’

‘How do you know I had a wank?’ I asked.

‘You were about to explode when I left,’ she said sitting opposite me. ‘And you will be again soon as it’s my turn to tell you about one of my best sexual experiences.’

I leaned forward on the sofa slightly. Jill had hinted a lot of kinky sexual experiences but never told me anything in any detail.

‘What were you thinking about when you came?’ Jill asked.

I might have blushed if it had been anybody else asking me but I told her about my nylon fetish and fucking Sarah’s arse.

‘Nice,’ she said when I’d finished, ‘I’ve been out with a couple of guys who liked stockings but I wouldn’t say they had a fetish about them.’

‘The first time I got fucked wearing stockings was quite good, would you like to hear about that?’ Jill purred.

My mouth was dry so I just nodded.

‘Feel free to remove your clothes and play with yourself,’ Jill said casually.

I looked at her with my mouth open, not quite believing what I’d just heard her say.

As I said, we’ve had lots of frank discussions about sex and seen each other partially clothed a lot but this was moving our friendship in a new direction.

‘I will if you will,’ I heard a voice say. It took me a few seconds to realise it was my voice!

‘Maybe I will,’ Jill said standing up and walking out of the door, ‘drink?’

I asked for a beer to calm my nerves.

Jill came back in again five minutes later with a couple of beers. She’d been to her bedroom and was dressed in her fluffy dressing gown and silk pyjama bottoms tucked into furry Ugg boots. Not the sexiest outfit but I knew from experience that the top that matched the pyjama bottoms made Jill’s nipples erect. I wondered if there was a way I could up the temperature of the living room to make her take her dressing gown off!

‘Come on, get comfortable and I’ll begin,’ Jill said taking a sip of beer.

I mentally shrugged and took my jeans off, sitting back down in my boxer shorts and t-shirt. I wasn’t sure if I should go any further but Jill seemed satisfied for now.

‘OK, the first time I was wearing stockings during sex was at a cousins wedding down in the Cotswolds. I was wearing my pale blue dress, the one I wore for your company barbeque last summer, and tan hold up stockings.’ She began.

I remembered the dress but I can only describe it as “teasingly see through but not actually see through but it makes her tits look nice”. A description my work colleague had come up with the following week whilst trying to describe it to a third colleague who was slightly obsessed with Jill but hadn’t made it to the barbeque.

‘The wedding was a little bit dull as I was hanging out with my parents for the early part of it but they went to bed fairly early and I got chatting to a guy in the public bar. I can’t remember his name, so let’s call him Paul. He was hanging out waiting for his mate to finish his shift, let’s call his mate John.’

‘No George or Ringo?’ I asked.

‘Not in this story,’ Jill winked. ‘We chatted and drank for half an hour before John finished and got changed. We were going to go to a night club down the street but John had been chatting up a girl from the wedding I was at and wanted to try his chances with her. I stayed in the bar with Paul, sitting in a corner table out of view of the main bar. It wasn’t long before what little inhibitions I had were totally gone and we were kissing and his hand was up my skirt stroking my thighs.’

I shifted position trying to hide my erection but realised I was kind of missing the point and shifted again so I could stroke my cock through my underpants as Jill continued her story.

‘We finished our drinks and I took him upstairs to my hotel room, fully intending to fuck his brains out! As we got to my door his mobile rang. It was John and he wanted to know where we were after getting nowhere with the girl he was with. Paul told him we were busy but for some reason I told him give him my room number and bring wine. I kind of expected Paul not to but he gave me a very dirty grin and told John what I’d said.’

Jill paused and drank some of her beer, watching me slyly stroke my cock.

‘Paul got my dress off before the door had closed and he was naked before we hit the bed. He had a fairly average cock but it was hard and I was ready. I left my shoes and stockings on but unhooked my bra and pulled my thong off. I pushed him back on the bed and mounted him, sticking my tongue down his throat for a French kiss as he shagged me. We fucked for a couple of minutes then there was a knock and the door opened. John had a pass card for the rooms.’

I wasn’t trying to be subtle about touching my cock now, this was hot! I had Jill’s lovely slim body and perky tits fixed in my mind as I imagined her riding Paul’s cock.

Jill continued, ‘John didn’t say anything, just smiled and stripped off. He approached the bed, his hard cock swinging between his legs. He was bigger than Paul but not by much. I took his cock in hand and started to suck him off as I rode Paul.’

‘Was this your first time with two guys?’ I interrupted.

‘Kind of. I’d been with two guys before at college but they took it in turns to fuck me, both losing their virginity to me. This was the first time having two simultaneously,’ Jill clarified for me.

Jill loosened her dressing gown revealing the little silk vest top I’d hoped she would be wearing. Her boobs moved delightfully under the thin fabric and her hard nipples poked through. I gave my cock a squeeze.

‘Paul came pretty quickly after John joined in so we changed places. John took me doggy style and I cleaned Paul’s cock with my tongue and mouth as he played with my nipples. John ran his hands up and down my thighs as he fucked me, finally reaching round to play with my clit. I’d already cum once fucking Paul but John gave me several orgasms in a row with his talented fingers. Paul was fully erect in my mouth when John finally shot his load inside me. John lay on the bed and Paul positioned me on my back next to him before fucking me for a second time. He lasted a little bit longer this time but not by much! As soon as he was done John took his place, sliding his cock deep inside my sopping wet pussy. He fucked me to three different orgasms as Paul watched then shot a fourth load of cum inside me.’

Jill ran her hands over her tits, tweaking her nipples as she recounted the last bit of her story. She kicked her Ugg boots off one by one and I was so engrossed in looking at her play with her nipples that it took me a minute to realise her feet were covered in tan nylon! I slipped my boxers down and pulled my cock free.

‘I knew you were a big boy!’ Jill squealed in delight at the site of my eight inch cock.

‘Is there any more to your story?’ I asked stroking my cock.

‘No, that’s it, they got dressed and left. I had a quick shower and went to bed,’ Jill said, ‘I do have something from that night though.’

Jill stood up, dropped her dressing gown to one side then pushed her pyjama bottoms down revealing a pair of tan hold up stockings and a flesh coloured thong.

‘Get naked.’ Jill suggested in a way that made it seem like an order.

I didn’t need asking a second time and striped my t-shirt and boxers off, looking at Jill for further instructions. Jill pulled her thong off, revealing her naked pussy, then sat sideways on the three seater sofa. Her hand went between her legs and she began to circle her clit with a finger. I joined her, sitting sideways facing her and wrapped my hand around my cock. Jill stretched one leg out, her toes softly teasing my testicles. I followed her lead extending one leg until my big toe was teasing the no man’s land between her pussy and arsehole. She shifted position so my toe was pressing against her arsehole.

‘Mm, right there,’ she purred at me.

Her toes pushed under my balls and I lifted up so she could press her big toe against my arse hole. The nylon covering her toes felt fantastic against my sensitive arse and I had to slow my hand down to stop myself from cuming too quickly.

We watched each other slowly wank, our toes pressing against each others' arseholes. I shuffled around until I felt her toe gently, partially penetrate me then pushed my arse against it in time to my hand movements. I stroked Jill’s leg with my free hand wishing I could reach her thigh from my position but knowing that was probably going to break the mood. Jill shuffled her bum pushing my toe into her anus. She moaned gently and my cock twitched at the sound. I wasn’t going to last much longer. I slowed my pace on my cock to try and extend the pleasure.

‘I’m close too, don’t stop,’ Jill whispered, watching me.

I sped up again, helped by Jill’s toe pressing harder against my bum. I stroked her ankle and calf, feeling myself getting ready to shoot. I aimed my cock at her leg and let go, shooting a long stream of cum on to her stocking. Jill moaned at the sight and I watched her neck and cheeks blush just before she came. Her legs shook with the orgasm, her toe wiggling delightfully against my arse hole causing my cock to twitch!

We untangled our legs, Jill holding her cum soaked calf up and raising her eyebrows. I leant forward and licked my jizz off her leg with my eyes locked on hers. When I’d finished we sat in silence for a couple of minutes before getting up and heading to our separate beds.