I had such a good response after telling the story of when my boss spent the day fucking every hole of my body that I’ve written about the time he begged me to fuck his virgin arse with the strap-on he bought for me. For those who haven’t read my other story (The day my boss fucked my cunt, arse and mouth) I had a six month affair with an old boss where we acted out a lot of fantasises… I was on the phone as he walked into the office, we’d been having an affair for about two months and he walked around to the back of my chair and started to kiss the back of my neck. As usual I could feel the trembling running down my back and straight to my pussy which started to twitch. I finished the call put down the phone and swung the chair around to face him asking him what he thought he was doing? With the usual smile on his face he lent over and pushed his tongue into my mouth. He pulled away and asked “What are you doing tonight?” knowing that his wife was away for a few days on business I replied “mmmm I think I’m washing my hair!” with that he laughed and said that he would be my house at the usual time and then disappeared back through the door… I spent the rest of the day thinking about other times that we had spent hours fucking each other until we were exhausted and instinctively knew that tonight would be a repeat performance. I left work at the usual time, went home and ran the bath while making myself a cup of tea. Then spent the next twenty minutes making sure there wasn’t any hair left on my body. I had never shaved my cunt clean before and just running my hand over the smooth skin made my body tingle all over. I quickly dried myself and went into the bedroom where I chose the flimsiest baby doll set that I have. I lay on the bed flicked on the TV and waited for him to arrive… About ten minutes later I heard a key in the front door, then footsteps on the stairs. He walked into the room with a bag in his hand which he put under the dressing table then bent over the bed and kissed me lightly on the lips. “I’ll just take a quick shower” he said as he walked back out of the room. I heard the water begin and couldn’t resist a quick peek at what was in the bag. I lent over the bed and pulled open the top. All I could see inside were clean underwear, shirt and deodorant, either he was going out after our session or was planning on staying the night which he had never done before… He came back into the room wrapped in a towel and climbed onto the bed to join me. As he lay next to me he run his hand up my thigh and under the baby doll up my stomach until he reached my boobs. He rubbed a nipple in-between his fingers I could feel his cock was already hard against my leg. We started to kiss as he moved his hand over to my other boob and tugged on the nipple. He pulled away and looked at me and asked “Would you like to try something different tonight?” I had been asking him for a while what his favourite fantasy was and replied “Do you really have to ask!” with that he kissed me again and said “I’ve got something in the bag I think you might like but I want to save it for later” I started to laugh and said that he was a tease. He giggled like a naughty boy and told me that I would have to wait a little longer… I then told him I had a little surprise of my own, took his hand in mine and pushed it down the front of my thong. His eyes lit up as he felt my newly shaved mound “Your such a horny little fuck aren’t you?” I laughed as he pushed his fingers further into my thong having a really good feel around like it was the first time he’d ever done it. Pushing two fingers into my slit he run them up and down covering them with my juice, he then pulled them out and into his mouth and licked them dry telling me all the time how fantastic I tasted… He then asked me if I had the silk ties handy. I started laughing asking him what he wanted them for. “Because I want you to tie me up”. I laughed again not thinking he was serious as whenever I has asked him before he said that he wasn’t interested. I got off the bed, pulled them from the draw and threw them at him. As I climbed back on the bed he pulled the towel from around him and threw it onto the floor, the big purple end of his cock was pointing towards me; I bent over and ran my tongue along the length around the bell end and back down to his balls. “Now who’s the tease” came from the other end of the bed. I put my hand round the bottom of his shaft to hold it still while wrapping my lips around the other end and moved down until my lips reached my hand. I carried on sucking and licking, making him gasp and groan as my tongue moved in the way I know he loved. I felt him stiffen, the base of his shaft pulse, then my mouth filled with his spunk. He put his hand on the top of my head until I had drunk every last drop… I released his cock from my mouth and picked up the ties off the bed, taking both of his wrists I tied the together then to the bed head. I then stood on the bed and placed each foot either side of his head before squatting above his face and telling him to fuck my cunt with his tongue. He ran his tongue over the lips of my pussy again and again and pleasure shot up and down my spine. Pushing into the entrance with just the tip like a little finger probing away, working its way further in each time he thrust. He sucked my clit in between his lips then licking away again lapping up my juices until I couldn’t hold on any longer and come all over his face… I stood up and looked at his shining face, “are you going to tell me what your surprise is now?” I asked. “Look in the bag” I told him I had already done that and as there was only clothes in it what was I supposed to do with them. He laughed and said that that would teach me to be so noisy and that I should have looked underneath them. I got off the bed and pulled the bag from under the table, emptying it on the bed. Out of it fell his clean clothes and then a lovely looking strap on cock. I guess my mouth must have fallen open at that point as he just started laughing… I looked at him and asked him if he was serious, “do you think I would have brought it if I wasn’t”. Looking at him lay there, tied helplessly to the bed, I grinned saying “I thought you were joking when you said that you wanted to know what it feels like!!!” I pulled down my thong and tried it on for size. I walked in front of the mirror moving from side to side to get a good look at it. I heard him laugh at me as I paraded around the bedroom rubbing my hand up and down the shaft telling him how I was going to give him a good seeing too… “You are serious about this aren’t you?” I asked one more time, giving him the chance to get out of it if he wanted to. He replied by turning over and lifting his arse in the air. I climbed onto the bed behind him; bending over I began by firstly licking his balls. He gasped and whispered “move up higher” I ran my tongue up towards his arsehole as he cried “Fuck, I’m coming!” I reached his hole and licked the edges before pushing in the end. After a couple of this I picked up a tube of lubricant and squeezed some onto my fingers, as I rubbed this into and around his hole he said “yes, yes, yes” over and over again. I slid in one finger trying to push in as much lube as I could, thrusting it in again and again… I then moved up near his face, pushing my cock into his face told him to suck it. The look on his face was of pure shock but I wasn’t put off. I pushed it towards his lips and again told him to suck it. This time he opened up and I slid it slowly into his mouth, he began to suck and lick as I pushed it further down to the back of his throat. When I groaned like a man his eyes opened wide, I pushed in again faster “do you like that?” he nodded his reply, “would you like me to fuck your arse now?” again he nodded as I pulled out… Covering my lovely fake cock in lube I moved behind getting ready to enter him. I ran the end of it across his hole a couple of times and asked him if he was ready. “Please, please fuck me” I asked him again if he was ready “Oh god yes, please fuck my arse, fuck me, fuck me” I pushed gently against his entrance forcing my way into his virgin hole. The end slid in slowly and when it had disappeared I asked him if he was ok. When he didn’t reply I carried on pushing it in further and further, about three inches of it was in when he groaned. I asked if he was ok “yes it stings a little but it feels great” I stopped pushing and said that he should let me know when he was ready to carry on… “No don’t stop keep going” I thrust a little further before pulling it out a couple of inches and thrust back against his body. I took hold of his hips just like I’d felt him do to me many times before and started to get into a rhythm, pushing it further into his arse with each thrust. It wasn’t long before he had all of it inside him, moaning with what I hoped was pleasure. Picking up the speed a little I thrust faster pulling it nearly all the way out before pushing it back in. “Oh god I’m going to come” he cried again as I thrust as hard as I could into him. I carried on like this for what seemed like hours when really it must have only been around 30 minutes, when he came for the third time he collapsed onto the bed and I slid out of him… He lifted his head off the pillow and then said “I think I’d like to go on top now”, I moved to the end of the bed and untied him. We then both lay on the bed kissing while wanking each others cocks. I felt him harden in my hand again as he pushed me onto my back. Straddling my hips he slowly lowered himself onto me groaning “oh god that’s good, that’s so fucking good”. Watching my lovers arse slide up and down a false cock with such pleasure on his face was making me wetter and wetter. I took hold of his dribbling cock and began wanking him again; his pace quickened pushing down harder and harder onto me. “Yes, yes, yes” he cried as he came over my hand and his stomach… He lay next to me saying that I was the best fuck he had ever had! He pulled the strap-on off me and buried his head between my legs, then pushing the fake cock into my wet pussy I came instantly over and over again. After a couple of hours sleep we had a quick bite to eat before fucking again… I do have other stories to tell of our time together and if you’re interested I’ll gladly tell them…