I walked in the office and he turned to face me. I waited until he spoke as I had been talking to Kim and she gave me some pointers. Finally he spoke and said "What's on your mind?"
I told him I was committed I wanted to do this, I asked him to be my teacher too. He paused and said, "I will think about it, in the meantime I will begin to train you. During this time I will be more patient because you're new to this. First off if ever you're being hurt and you want it to be stopped just tell me "cry uncle", that will be my way of knowing I have gone too far and I will stop.
"Just so you know Kim has the same phrase to use, but has never used it but its there for your protection. Second you are going to be tested to see how willing you actually are so be prepared. Third until I decide to fully train you, you may stop at any time just come into my office and tell me and you can continue to live here. After I have taken you on, if you decide to end the arrangement you will end it by moving out! Is this understood?"
I nodded and as I turned to leave Tim said "Where are you going I haven't told you, you can leave." I swallowed hard as I just came to a realization that this is for real, but I knew I wanted to do it. I turned back as Tim said, "Go to your room and put on your most revealing underwear, the ones that you think are the sexiest and meet me in my bedroom in five minutes."
My heart was racing I was excited I didn't know what to expect but I knew I was looking forward to it. I couldn't get changed fast enough and I think I made it back in less than two minutes. As I entered the bedroom I was not prepared for what I saw, there were two wool lined leather cuffs one on each foot of the bed and two more on the posts. Tim was naked except for his shorts and I thought he was a little excited as it looked like he was getting hard.
He made me get into the cuffs facing the bed so that each leg was tied to a bed leg and my legs were spread wide open. The other cuffs made me lie forward on the bed and I couldn't move but for a few inches. Tim then sat on the bed facing me; he smiled and said "I hope you're ready for this."
With that he took off his shorts and I could plainly see his cock wasn't hard at all it was just very thick. He reached over to the night stand and grabbed a tube of lube. Seeing this I thought "I really don't need that," I was getting very wet already and although he seemed large I had never had any problems in the past. He then started to stroke himself and it didn't take long before he was very stiff and though he wasn't huge, he had a thick cock.
He got up behind me and basically ripped my thong right off me. I could hear him squeeze the tube of lube but I was totally taken aback when he started to rub the lube into my anus. Now I started to get nervous I was a virgin there and though a few fingers have found there way in there, that's all.
I could feel his penis as he rubbed it over my butt, then he placed the head right at the entrance and started to push. He said, "Try to relax I will go slowly and you will find it easier to just let it happen."
It seemed like an hour, I could feel the head of his cock in my ass and I was biting my lip. It wasn't painful, as he was going slowly, but it seemed like it wasn't going to fit. Then all of a sudden he pulled out. He didn't speak he just went over to a part of the room I couldn't see and when he came back I felt something much smaller being placed where his cock was just a moment before.
This slid in must easier and after it was in Tim said, "I guess you weren't ready for me yet but I want you to use this butt plug daily and after you find it easy to get it in, I will give you a larger one." He then left the room. I was comfortable but pantyless and horny with my arms and legs tied to the bed.
I was resting with the plug when Kim came in. She sat on the bed and just smiled at me. She put her things away and without a word as she put a finger to her lips for me to be quiet she got undressed and put on a robe. She left the room and came back a few minutes later with Tim.
This time they both lay down on the bed and as they kissed, Kim's robe fell open revealing her breasts. Tim went to work on her nipples as I eagerly watched. I was getting hornier by the minute, as he reached between her legs she eagerly opened them to accept his finger running over her pussy. Then Kim got on her knees as Tim lay down and she took his member in her mouth.
Being soft she could barely get some of it in her mouth and as it grew larger she could only fit the head and a little more in her mouth as her hand simultaneously stroked him. I could now see his cock glistening with her spit as she stroked it up and down. She did this for a few minutes until Tim rose and let Kim lay on her back with her pussy facing me, her knees raised slightly and her legs wide apart.
Tim then proceeded to mount her and I had a ringside seat. I had never seen anyone have sex before but it was very exciting and I wished I could get my hand free so I could stroke my aching clit. I wanted to cum so bad at this point but all I could do was watch.
In a while I heard Tim say to me "Do you want my cum?"
At first I didn't know what he what talking about but when he spoke again he said my name first so there was no mistake. I had only had a guy cum in my mouth once before and it wasn't the most pleasant experience but now I was so horny and afraid to say no I blurted out yes yes I want it. He increased his speed a little and shortly he got off Kim and I found myself with the purple head of Tim's cock coming right for my mouth.
I opened my mouth and was barely able to get the head in when the first spurt shot to the back of my throat. I closed my mouth around his cock head afraid to do anything else as I felt each pulse and spurt of his cum in my mouth. Soon though I couldn't hold it in and it started to leak out the sides as I tried to swallow but I found it difficult with his cock in my mouth.
I managed as he was done shortly and he pulled his cock out of my mouth. I swallowed what I could as I didn't know what else to do. I don't remember the taste at all, I was still so excited. Tim got up from the bed and slowly pulled the butt plug from my ass and then back in again, he did this for a few minutes. I was so hoping to get something or someone to touch my clit because at this point I was ready to explode; only I knew it wasn't to be yet.
Tim left the room and Kim got cleaned up and came back and untied me. I said "I need to cum so bad," she told me I needed permission and Tim was the only one to give it. I just wanted to reach down and rub my clit once I know that's all it would take and I started to do just that when Kim's hand grabbed mine and said,
"I wouldn't do that if you know what's good for you." Needless to say I didn't. She gave me some clothes I was to wear that night, if you can call them that. It was a pair of shear panties and a demi bra that only lifted my size C breasts and exposed my now very hard nipples.
Kim motioned for me to follow her, we went out and I helped to cook dinner, that is to say I served everything she gave me to Tim. He did his best to tease me every once in a while, accidentally rubbing one of my nipples which sent shudders through me. After dinner Tim made me sit at his feet and he asked me how I liked my first taste. I was careful when I said,
"Teacher I was so excited by everything I really enjoyed myself but," at that word he stopped me and said,
"If you were looking for regular sex you won't get that here, I know you want to get off too. Do you want to rub your pussy or have me lick it till you cum? Well I don't think your are ready for that kind of reward yet so you will just have to wait. You are forbidden from masturbating or doing anything that would make you cum until I tell you it's ok or I make you cum myself, is that understood?" I nodded in understanding.
Virgin No more
A few weeks went by and I was witness to a few other things always preceded with a butt plug for me and being tied up somehow. Saturday began a little differently as I awoke, I now had a bed by the closet in the master bedroom, I would occasionally get to sleep in the big bed, but mostly in the small bed.
This Saturday Kim had left early she had to do some errands and when she left she told me to climb in bed next to Tim and just sleep until, well I would know when. Well I knew when alright. Tim got up wen
t to the bathroom to relieve himself and came back to bed to see me lying there he smiled and gave me a kiss. Actually the first one full on the lips. I did enjoy it when a man envelops you with his arms and gives you a deep soul kiss.
He then ran his hand over my back all over my nude ass and gently cupped one of my breasts. He then tenderly kissed it and sucked the nipple in his mouth and rolled it around his tongue. It felt delicious. It didn't last too long as he then broke away and told me that he wanted me to make him cum without using my pussy and if I did well he would reward me. With that he smacked my ass once good and hard and I instantly got flush with excitement.
Well I soon was working on his cock with my mouth and hands stroking him and sucking for all I was worth. I must have been doing something right because soon he started to moan and I just kept at it with more enthusiasm. I wanted the reward, whatever it was, so I started to lick for all I was worth the underside of Tim's cockhead while stroking his massively thick cock up and down.
Soon I could tell he was going over the edge and within a minute he was cumming spurts in my mouth. I was careful this time and didn't spill a drop and swallowed every last bit. I even remember it tasted a little salty with a sweetish aftertaste. I was so proud of myself I was smiling from ear to ear when Tim said, "Now I want to see you rub your pussy."
I was disappointed to say the least, I thought I was going to have some help or something, I didn't expect this at all. I guess my face must have shown it too because he then said. "If you don't like that idea then you don't want to cum that bad do you?"
At which I replied, "Yes I want to cum so bad teacher please let me."
He relented and I proceeded to rub myself. It was more exciting than I ever imagined as I had never masturbated in front of anyone before and I was so turned on by what had just transpired too. I was getting real wet and I could feel myself just start to get close when he told me to stop.
I was dumbfounded but I did as I was told and when I opened my eyes to look at Tim I noticed that he too was masturbating while watching me. He was hard again and I was so excited when he told me to get on all fours. He got behind me and placed that cock right at the opening of my cunt. He slowly pushed it in and as it slipped in to my wet folds and filled me up he said, "Now you can finish what you started."
He reached around and cupped my breasts which by now were burning for attention and I rubbed my clit faster than ever. When I was at the point I was ready to cum again, again Tim said, "Stop for a moment then start up again slowly, I want you to prolong it until I tell you to cum."
I did just that and this game went on a few more times until finally he started to pound his cock into me harder and faster than before and he told me, "Now you can cum any time."
Well that did it I came and I came and I flooded his cock with my juice. I was so wet and cumming so hard when he moaned and stopped stroking signaling his own climax. I was as spent, as the orgasm I had faded, when I got spanked and this one was just as intense and pleasurable but totally different.
After Tim came he slumped down on me and we kind of rolled onto our sides with him still filling me up with his manhood. It felt so warm and I wished he would have stayed hard but soon he slipped out and I could feel the warm cum and my own juices flow out of my pussy soaking me and the sheets. Tim just held me though and wouldn't let me move as we lay there.
After I got over my embarrassment of leaking everywhere I just lay there in his arms as he just gently held me close. I could feel his breath on the back of my neck as his breathing slowed and became more regular. I soon was in an almost sleep state it felt so good to be close to him after just screwing like we did.
Nothing would interrupt our embrace and nothing did for soon I awoke to find Tim gone and the covers pulled over me. I looked at the clock and I must have been asleep for 2 hours. I got up with a start only to find Tim sitting in a chair watching me. He smiled and he told me he was just admiring my beauty as I slept. I blushed and hurried to clean up.
I had been using my butt plug for a few weeks now and had even graduated to a larger one. So after I cleaned up Tim said he needed to do one more thing before we showered and dressed for the day. I was to assume the position at the end of the bed in the leather cuffs. I knew what this meant but now I was ready.
Tim started by fingering my pussy and clit. I started to get wet again and soon he had me moaning. He even took his cock and slid it in my pussy for a few minutes and this felt really good. He had already gotten the lube and put it on the bed so while he was stroking his cock in my slick cunt he began to lube my ass.
First he inserted one finger then two and he was matching his strokes with his fingers. If he did this too much longer I was going to cum again, but it wasn't to be as he slowly pulled out and placed the tip of his cock where his fingers were and slowly pushed it in. It went a lot easier this time and soon he was all the way in and I was stretched but it felt good.
He slowly stated to pull out to begin stroking in and out and as soon as he did this he reached around and started to rub my clit with his fingers. I was soon in heaven and I felt great. His rhythm increased as he was now going faster than I ever imagined he could go in my butt and his fingers were matching the speed.
I was now going over the edge, about to cum more now in a short span than I ever have before, he kept rubbing as he was close himself now as I could feel the tempo increase slightly and that sent me over the edge. I came with a shudder and he continued to rub me and within a few seconds I was coming again and again and again.
It wouldn't stop and I could feel myself involuntarily spasming my muscles in my ass and this sent Tim over the edge as he grunted in his release and slowed his stroking but not his fingers, which continued as I kept riding the wave of pleasure that swept over me again and again. I didn't even notice his cock was no longer in me when I stopped cumming.
Tim just unbuckled the restraints and picked me up and lay me on the bed and disappeared in the bathroom. When he reappeared he picked me up again and carried me into the bathroom and lay me down into a nice warm bubble bath he had run in the Jacuzzi. He set the timer for 20 minutes on the tub said enjoy and left me to enjoy my bath in my orgasmic state of bliss.
Kink Time
Tim likes to watch football with his friends on Sundays and usually Kim and I serve the men snacks and drinks and generally stay out of the way. Most times it's crowded and noisy so they don't pay us much attention so we can relax and chat. This one particular Sunday was different.
First off only Tim's best friend Kirk came over. He is a nice looking guy pretty tall and muscular. Then Tim told me to dress in a short skirt and forget wearing panties. He also said to wear the sheerest bra and shirt I owned. He further instructed me to do whatever possible to get Kirk turned on without ever touching him. Tim said I would get a great reward if I was successful.
I was intrigued to say the least and Kim offered no hint on what he was up to as she didn't have a clue. I must admit I was a little turned on by this game I was about to play. My pussy was freshly shaved from my morning bath and with the skirt I chose just bending over a little would show my ass and my pussy lips to whoever was looking in my direction.
Kirk arrived and I answered the door and his face certainly lit up when he saw my nipples through the lace bra and thin shirt I was wearing. I got him a beer and clumsily knocked the remote on the floor. When I bent to pick it up my ass was just a few feet from his face and as I picked it up I could see Kirk staring at my behind with a stare that I knew I was going to get him turned on real quick.
I made excuses to go in and tidy up and move things around and Tim was smiling knowing what I was doing. Kirk was very attentive to me and when Tim ask him about the game he almost always had to say sorry missed the play or I didn't catch that. I could start to see a noticeable bulge in Kirks pants and this made me smile even more.
Tim saw this too and when Kirk excused himself to go to the bathroom Tim told me to follow him an
d give him the blowjob of a lifetime. Well the door wasn't locked and Kirk was a bit surprised when I walked in and smiled when I said I wanted to help him relieve himself. I had never watched a man pee before so I watched as he finished. When he was done I think I surprised him how fast I took his cock in my mouth.
It got hard in an instant, not that it was that soft to begin with. He was longer than Tim but not as thick so I had no problem getting it in my mouth, I could almost swallow the whole thing before I had to come up for air. I was licking and stroking quite fast when I heard Tim shout to hurry because the game was on but Kirk wasn't going anywhere soon.
I didn't take too long and Kirk gave me a huge load of cum. I tried to swallow it all but as always happens it comes too fast and some always seems to escape my mouth. When he was done I placed his limp cock back into his pants and he zipped them up, he quickly mumbled thanks and left. I cleaned up and followed.
When I got back to the couch I acted as if nothing had happened and so did Kirk but Tim wasn't having any of that. He asked Kirk, "What took so long?"
Kirk started to stammer and Tim just started to laugh. Then he said, "Did you enjoy your blowjob?"
Kirk was shocked to say the least but Tim continued to say, "Would you like to fuck Stephanie? She is very pretty and she will enjoy it as much as you do."
Kirk didn't know what to say at this point. I could see he was a bit uncomfortable but Tim didn't let up. Then he said, "Steph show him what a great pussy you have and what nice breasts you have. Why don't you just strip for Kirk right now and show him how much you like to fuck?"
Well, I was surprised too but I wasn't about to disappoint Tim as he was the boss and anyway Kirk was very good looking and I had already sucked him off. So I did a little dance while I took off my shirt then my bra then my skirt. With that I knelt down and crawled up Kirk from the floor making sure to feel his cock to see if I was getting him hard again and sure enough it was.
Filthy Daddy's Taboo Erotic Sex Stories Page 44