Would you like to help us fulfill a fantasy? said the message on my phone.
My heart fluttered a little as the message was from Cathy, a young lady who had been working for me until recently. We’d bonded over our love of classic 70’s rock despite an age gap of twenty-five years and had grown close and a bit flirty with each other. We’d also had several long, sexual discussions on messenger since she’d left the company discussing fantasies and fetishes.
She’s very androgynous with short, nearly black hair, small boobs with pronounced nipples (she goes braless under thin vest tops), slim hips and long legs. Not my usual body type at all as I generally prefer curvy ladies with big bums, but she had been the subject of a lot of masturbation fantasies over the last year. Especially when she wore short skirts, fishnets and DM boots to work.
Yes, what did you have in mind? I wrote back.
There was a frustrating delay as she typed her reply but eventually it popped up on my screen:
How would you feel about spanking Dan while I watch and masturbate?
I was immediately hard with excitement. I’d met Dan, her boyfriend, a couple of times and he was a good-looking guy with long blonde hair. I knew from conversations with Cathy that he was bisexual, liked to wear stockings when they fucked and that she pegged him on a regular basis.
Cathy knew I was very open-minded in terms of sexuality from our conversations and I had described my own pegging experiences with a married woman I occasionally got together with. I also told her about an MMF threesome I’d taken part in a couple of years ago and I had described loving the feeling of another man’s cock pressing against mine as we double penetrated the woman.
Sounds like fun. Will it be OTK and Is there a dress code? I replied with a smilie.
Yes, OTK. He’ll be wearing stockings as you both get off on that. I’ll be wearing a fishnet bodystocking and high heeled boots. We’d like you to be naked and trap his cock between your thighs as you spank him. Just a warning, he will probably cum as you spank him!
OK, good to see you’ve thought about this. When? I replied with some relief that they had thought about what they wanted to do. I figured they’d be less likely to chicken out. That had happened once when I met up with a couple that wanted me to join them for a threesome.
Our house tomorrow afternoon? The other flat mates are going to be away so we can make as much noise as Dan likes! came the quirky reply.
I got the addresses and went for a wank to calm myself down. Halfway through my phone beeped and there was an additional message with a mirror selfie of the two of them mooning me! I finished myself off looking at two smooth, slim bums - one with a hint of pussy lips, the other with a hint of smooth testicles!
I turned up at the house at 1pm the next day. It was a big, old detached house converted for student lets. Cathy opened the door in her dressing gown and I could see her high heeled, platformed stripper boots underneath. She said hello and kissed me on the cheek then led me into the shared living room.
Dan was stood in the corner wearing black stockings, combat boots and a white apron.
‘Would you like a drink, Sir?’ he asked.
‘Beer, please,’ I responded and Cathy asked for the same.
He left for the kitchen and Cathy giggled as he exposed his bum to us on the way out. I could see his stockings were held up by a black leather suspender belt.
‘Dan’s suspenders are very rock,’ I commented, feeling my cock harden.
‘If you like those, you’ll love my boots,’ Cathy responded slipping out of her dressing gown.
As promised, she was wearing a fishnet body stocking and boots. The boots were thigh-high leather with high heels, two-inch platforms with studded leather bands around each ankle. The bodystocking was crotchless, giving me a glimpse of her shaved pussy. Her hard, long pink nipples poked through the tight fishnet.
‘Fucking fantastic,’ I muttered, pulling my shirt off to reveal my pierced nipples and muscled, hairy chest. I was now fully hard.
Dan walked in with a tray with a couple of bottles of beer on it. I took mine and took a deep drink. He put the tray on the coffee table and stood waiting, a very visible bulge pushing against the apron.
‘I need a glass and fetch a second beer for our guest, that one is almost half gone,’ Cathy said firmly.
Dan picked up his tray, bending from the waist to show me his arse then walked out to the kitchen again. I watched him go, my cock pressing almost painfully against my jeans.
Cathy seated herself on a leather sofa and motioned me to the one opposite.
‘Are you ready to spank Dan?’ Cathy said, breathing heavily.
‘When he comes back in?’ I questioned.
‘Yes, I was going to build up the scene a bit more, but I can’t wait. Get naked,’ Cathy said, taking a long pull of her beer.
I stood and gratefully removed the rest of my clothes, my cock springing to attention as I freed it from my boxers. Cathy purred in appreciation, drinking more beer and parting her legs to show me her wet pussy lips. I sat back down and stroked my cock in appreciation as Dan walked back in.
‘Too slow, time for punishment,’ Cathy said sternly pointing to my knees, ‘remove your apron and assume the position.’
Dan removed the apron with almost indecent haste, his long cock bouncing in front of him. His cock was longer than my seven inches by an inch or so but lacked my girth. Cathy opened her legs, putting her feet up on the coffee table and stroked her wet pussy. I moved forward on the firm sofa, so I was sat upright and motioned Dan to bend over my legs. I opened my legs and his cock slipped between my thighs. I moved my own cock and balls to get comfortable, my cock pressing against Dan’s hip and my hands on his back and thighs.
I’m six foot three and Dan is five foot eight and weighs nothing compared to me, so he fit across my legs easily. His hands went to my left calf and started stroking it as I glanced at Cathy to make sure she was watching us. I stroked my hand over Dan’s stockings before slapping his left then his right butt cheek.
Cathy and Dan grunted in pleasure simultaneously making us all giggle a little. I spanked him again, this time slapping him three times on each cheek before stroking his legs through the stockings, something I really get off on. I could feel his cock against my thighs and squeezed it on the last couple of spanks. Cathy was slowly pushing two fingers in and out of her pussy as she stroked her clit, her eyes greedily devouring the sight of me spanking her boyfriend.
I slapped Dan again a little harder, five times on each cheek this time. I squeezed his cock with my thighs and felt him thrust against me each time my hand landed on his bum. He kept his grip on my leg, stroking one hand up and down. I glanced at Cathy and she was frigging herself with three fingers, looking like she was close to orgasm. I felt precum escape from my cock on to Dan’s hip and spanked him again. This time I gave him ten hard slaps on his bum making it redden. He groaned loudly on the last couple of strikes and I squeezed his thrusting cock as hard as I could with my thighs and was rewarded by hot, wetness on my skin as he shot his load. I spanked him four more times as he squirted a second time then let him relax, gasping for breath still bent over my legs.
I stroked his bum, then gently parted his legs to stroke his thighs as Cathy brought herself to orgasm watching us. Dan remained where he was moaning softly as my hands explored, stroking his balls and gently partying his cheeks to run my fingers over his anus. He shivered visibly as I gently pressed my finger against his arsehole.
‘Finger his arse,’ Cathy commanded, surprising me by throwing a bottle of lube over.
Dan moaned as I moved my fingers back to his arsehole, this time squirting some lube on it and pushing my index finger into him. He shivered again as I penetrated him deeper with my right index finger, stroking his back with my left hand. Cathy stood and walked towards us, grabbing my beer and offering me a drink as I worked my finger deeper into her boyfriend’s bum. I drained half the bottle, mouth dry with excitement as I anally abused my first twink. I randomly thought that fingering Dan in the arse wasn’t any different to fingering a woman physically, but I found it way more exciting mentally.
‘Two fingers,’ Cathy said softly as she put the beer bottle back on the table.
I slipped a second finger in, adding more lube on the basis that you can never have too much. I stroked Dan’s balls with my little finger as I finger fucked him. He moaned again and I felt his young cock harden against my thigh again. Cathy leaned forward and spanked Dan’s thighs then raked her nails over his bum as Dan’s arse opened and greedily accepted two long fingers.
Cathy straddled Dan’s legs so she was facing up his body then, grasping my wrist with her right hand, started guiding my movement in and out of Dan’s bum, moving my hand faster and deeper than I was doing. Her left hand moved down Dan’s hip and found my hard cock, rubbing precum off the head then licking her fingers.
‘How do you fancy fucking your first boy?’ Cathy asked after I’d been fingering Dan’s arse for a couple of minutes. I felt Dan twitch on my legs.
‘Yes, please,’ I whispered, not trusting my voice not to crack.
Cathy pulled my fingers out of Dan’s arse and told him to stand up. He did so, wobbling a bit as blood rushed back to his legs. I saw that his cock was fully hard again before Cathy moved him to the arm of the sofa and bent him over. She motioned for me to follow and applied more lube to Dan’s arse as I got into position behind him, then took hold of my cock and spread even more lube over its length.
I stood behind Dan, running my hands over his stocking-clad legs, thinking quite randomly that he had better legs than quite a lot of my previous girlfriends. I spread his butt cheeks and pressed my cock against his anus. He was the perfect height bent over the sofa arm and I slipped the head of my cock into his bum, making him moan with pleasure. Cathy stood beside me, watching my cock slowly disappear inside her boyfriend.
‘You’re his third cock but the first one I’ve got to watch,’ she whispered, stroking her boyfriend’s back.
I pushed my cock the rest of the way in then stopped, letting Dan get used to my girth. I played with my pierced nipples, pulling the rings to stretch them. Cathy gasped as she watched then moved her right hand to my bum, keeping her left stroking Dan’s back and bum.
‘Fuck him,’ she demanded, ‘start slow and gentle but I want you to be slamming your cock in and out of him by the time you cum.’
I pulled halfway out then sank my cock back into Dan. He looked back over his shoulder at us with an expression of pure pleasure.
Encouraged, I pulled out further and pushed back in harder and deeper this time. Cathy slid her hand over my buttock and her fingers found my anus, probing gently, her fingers still covered in lube. I opened my legs slightly, trying to encourage her to touch me. Her fingers found my arsehole and slid in. I pushed back against her in encouragement and felt a second then a third finger slip in.