I was taking classes at a local community college when I was 21. I was a handsome young man, athletic and of course always horny. I was between girlfriends at the time and had taken an hour ride to the nearest adult novelty store. The clerk appeared to be mid-thirties and had a sexy and dominating appearance. I found my way back to the video rental section and soon found myself drawn to the more kinky rentals. This was back before internet, and being from a small town in the country, I had no idea that people even did the stuff I was seeing, but the boner in my pants told me that I liked it. Specifically, the ones with the pictures of women in charge, doing all sorts of kinky stuff to the men, even fucking them in the ass with dicks that they had strapped to their waists. Another was making a guy lick cum from her pussy. This stuff was blowing my mind. I couldn't imagine any of my preppy girlfriends ever consider doing anything like that, but it had flipped some sort of switch in my head, both of them! I really wanted to find a woman to sexually dominate me, but give where I lived, I definitely didn't expect it to ever happen. I continued browsing the store and ended up in the sex toy section where I saw a strapon for the first time. There were several on the wall of various sizes. It just so happened that the clerk had a good view of that section and had noticed me lingering. I heard her call out to me asking me if I had found one that I liked. My face turned bright red with embarrassment. I quickly replied that I was just looking. She replied that it was too bad, and that she thought one of those would look hot in my cute ass. OMG! I was freaked, but turned on, and out of my element. I grabbed a swingers magazine and checked out. Needless to say, I ravaged myself in bed that night. Remembering the image of the guy eating cum from the woman's pussy, I scooped a bit of my cum from my chest and tasted it, and then some more, until I had eaten it all.
Several days later, my mother asked if could take her coworker, Ann, to college as her car was in the shop. I had seen her coworker before, late 20's, a bit curvy, and quite attractive. I had rubbed one off thinking about after meeting her for the first time. I was more than happy to give her a ride. I picked her up at her place, a nice apartment in town. I was not disappointed, she still got my blood flowing. We had a 30 minute ride to the campus, and chatted, eventually getting to the subject of girlfriends and boyfriends. She had been seeing someone, but he took a job too far away for them to continue dating, and I was still between girlfriends. She asked if there were any prospects and I told her that I sort of doubted it. She asked why would that be? It was now or never I guess and I asked if she would keep what I said between us. She agreed. I told her that I loved sex and making my girlfriend cum more than anything, and that I would like to find a slightly older woman, one that loved sex as well and would sexually dominate me. Of course her eyes got wide, and she came back with, "Really?" I told her about my trip to the adult bookstore and the pictures on the video covers. She asked which ones I liked and I told her about seeing a guy tied to the bed and his mistress was riding his cock in one picture and he had a toy in his ass. Then, another picture showed her sitting over his face and he was eating his cum out of her. Then I told her about the guy being fucked in the ass with a strapon. I told her that I hoped to one day find a woman that would like to do those things to me and maybe more. I was waiting for some sort of put off comment, but instead she said that perhaps she should take a trip to the adult bookstore, and we both chuckled. We parked a the college and went our separate ways, agreeing to meet in the cafeteria before heading back. I was finished first and waited for her arrival. About 20 minutes later she met me and we headed back to the car. I asked her how class went and she said that it could have gone better and I asked why. She gave me a knowing look and said that she had been distracted thinking about our earlier conversation. I gave her a quick, oops sorry, and we got in the car and headed back home. She asked if I had tried any of that kinky stuff before, and I told her no. She asked if I had ever tasted !my cum and I hesitantly said yes. She asked if I liked it,and I said that it was OK, but that I thought it would be better if I was being forced to eat it, to which she replied, "I bet it would." Her response sure surprised me and I started to feel submissive toward her. Then she asked if any of my girlfriends had ever put their finger in my ass while I was getting a blow job. I had never heard of such a thing and answered that they had not. She said that was too bad, and that she bet I would really like it, and that I might even like something even bigger up there, wouldn't I? I gulped and said I'd like to try someday.
The ride home was almost over, and I was full of sexual tension. I could not wait to go home and rub one off. I planned to drop her off and head home, but when we got there, she told me to park and come in with her. After we got in the apartment she handed me a bottle of wine and asked me to open it, as I opened the bottle, she retrieved two glasses and told me that she thought I could use a glass. She was right, of course. My heart was pounding and my mouth was dry. We went into the living room and she sat on the couch and I sat in a chair a cross from her. We sipped our wine and then she said, "So, you want to be sexually dominated by an older woman....Would you like to be my little pet?" I responded with "Yes ma'am." She told me to finish my wine and then she said that I was over dressed if I was going to be her pet. She told me to go take a shower and to come back naked. I went to her bathroom and quickly stripped and waited for the shower to get hot. Once in the shower, all I found was very perfumed soap and shampoo, the same fragrance that I had been enjoying sitting next to her in the car. I quickly scrubbed my body, making sure to get all the naughty parts and dried off. I hung up the towel and slowly walked back into the living room. My hardon entered the room first! She had me stand in front of her so she could admire and embarrass her new boy toy. She told me to get her another glass of wine. I returned with the glass of wine, my boner still on full display. She stood up and took the wine from me and then circled me, ever so close. She ran her hand over my ass and then around to my cock, which she gave a firm squeeze and sipped her wine. She asked if I would like to bathe her and of course I said yes. I filled the tub and waited for her to come in. She entered the bathroom wearing only a towel. She handed me the towel as she stepped into the tub. She was a vision, a goddess that I wanted to worship and serve. She had me wash her beautiful body and as I did, I committed it to memory. She asked if I thought her toes were clean, holding up one of her sexy feet to my face. I opened my mouth and she slowly inserted her big toe. I made sure to check them all and then again on her other foot. She raised up to her knees and faced away from me and then bent forward and asked if I would lick her ass. I had never done anythng like this before, but bent in and slowly began working my tongue around her asshole. She let out a little moan, so I guess she it was something that she liked and I guess I would be doing it in the future.
I toweled her off as she emerged from the tub, taking in her beauty. She grasped my hard cock and led me to her bedroom and told me that she needed my tongue again and told me to lay down on the bed, face up. She climbed over me and lowered her sex to my face. I savored her scent as my tongue worked to give her pleasure. She shifted her hips so that my tongue was now in her ass. I kept licking and noticed her fingers were now playing with her pussy, sliding with purpose between her silky lips and around her love button. She urged me to eat her ass, talking dirty to me, she called me her asslicker, and asked if I wanted to eat cum from her pussy and get fucked in the ass. I managed to get out a yes between licks, and added, "Please make me your bitch!" That was enough to make her body shudder with an intense orgasm. She had me spoon with her while she recovered. She asked me if I would like my reward for giving her such a wonderful orgasm. I said Mmmmmm in agreement. She asked if I had ever had a naked massage. I hadn't, and was about to have one that I would never forget. She brought out some lotion from her night stand and had me lay face down and legs apart. She knelt between my legs and poured a generous amount of lotion into her hands and started massaging my shoulders and back. Her hands felt magical as they glided across my body, both relaxing and arousing me. More lotion and her hands began drifting lower and lower until they were just above my ass. Another generous squirt of lotion and her hands were kneading my ass cheeks like they were large lumps of dough, with slippery fingers brushing against my anus, making me moan. Her fingers began focusing on tight little asshole, circling it and pressing against it as they slid up and down my crack. I found myself yearning for one of those fingers to slide inside me. I heard her open the lotion again and heard it squirting into her hand. I was expecting to feel her hands on my legs, but they went back to my ass, spreading my cheeks and exposing my asshole. Her fingers slowed and I felt one right at the edge of my sphincter. With one smooth push her lubricated finger was buried deep inside me and then began thrusting in and out of me. The sudden penetration took my breath away, but aroused me even more. I could feel my asshole begin to relax and so could she and I soon felt a second finger invading me, stretching me even more. She took her time and added more lotion to her fingers. Her fingers began to twist and thrust her fingers, trying to open me up even further. She had pulled her two fingers almost all the way out, and thrust them in again, but this time adding a third finger. I gasp and felt a burning sensation in my sphincter. She told me to relax as she continued working her fingers in and out of me. Satisfied in her progress of stretching my ass, she lifter my leg and ducked under it, keeping her singers in me. Her face ended up in my crotch. She opened her mouth and expertly began sucking my aching cock. The combination of her fingering fucking my ass and her wonderful mouth devouring my cock like it was her last meal had me quickly building to an incredible climax. My breathing became quick and shallow and I was sounding like a girl in a porno. I couldn't hold back any longer and I announce I was about to cum. She kept me in her mouth throughout my entire orgasm. My breathing relaxed and became deeper as I began to relax. Her fingers slipped out of my ass and my cock slipped from her lips. I was laying on my back in post orgasmic bliss when I felt her move up next to me, and cuddling me. She pulled my face to hers and kissed me, forcing her tongue and my cum into my mouth. I was a bit taken off guard, but settled into a long erotic cum kiss before she told me to swallow it.
We showered together afterwards, cleaning and admiring each other's bodies. My admiration was more of worship, while hers was more of conquest. She asked me to spend the night and we climbed into bed together. She spooned with me and told me that we would have to go to the adult bookstore the next day and that she wanted me to show her the pictures and toys that I had seen. She rubbed my ass and told me that we would have to find some fun things to stick in my ass. She asked if I would like that and I told her yes. Her hand slid around my hip and found my growing cock. She told me that it seemed like he liked the idea too. She kissed my neck and released my cock, telling me to get some sleep. That was easier said than done after feeling her fingers wrapped around my cock just a shot while ago. Eventually, I did get to sleep, and with a beautiful dominant woman snuggled next to be in bed. Life was good.
I made Ann breakfast in the morning and then ran home to change clothes and grab another shower. Of course thought of Ann while I was in the shower, but made sure not to cum. We had set a time for me to pick her up for our trip to the adult bookstore. When I arrived, I found her dressed in a sexy yellow sundress and sandals. I found out while we were driving that she wasn't wearing any panties. As I was driving, her hand rested near the bottom of her sundress. Each time I glanced over, her hand and dress were a little higher until I started to see her trimmed bush. Her fingers explored her pussy and she opened her legs further to get better access. The faint aroma of her sex began to build my own arousal. She presented me with a very moist finger and I immediately opened my mouth to savor her flavor. She did this several more times during the drive and by the time we got to the store we were both as horny as a couple of lovers on prom night.
When we entered the adult novelty shop I immediately recognized the clerk from my last visit and it appeared that she recognised me as well. Ann, or should I now say Mistress Ann and I went back to the video section and looked at the video boxes that I had looked at on my last visit and also went over to the toy section and checked out the strapons. I noticed that the clerk was watching us pretty closely and had sort of a wicked grin. While in the strapon section, the clerk acme up and introduced herself as the owner of the shop, and as Mistress Rebecca. She asked if we had made a choice or had any questions. She recommended a moderately sized life-like strapon and said that it would be a good starter strapon if that was what we were looking for, adding that she thought it would look very sexy in my ass. She paused and then said it would look sexy in either one of you and gave a brief chuckle under her breath. Then she became more bold and asked Ann if I was her pet. Ann chuckled and said that you could say that. Mistress then told Ann about the store rules regarding pets. She said they must be collared and on a leash while in her store. She walked a nearby rack and grabbed a leather collar and handed it to Mistress Ann, who buckled it around my neck. She said that she kept leashes at the store entrance that could be borrowed while in the store and sent me over to retrieve one. Mistress Ann clipped on the leash and then Mistress Rebecca lead us around the store recommending butt plugs, lubes, restraints and one other fetish stuff. When you added up the prices of it all, it was a little overwhelming and I think Mistress Rebecca realized that. Mistress Rebecca requested that Mistress Ann send her pet to the car so at they could chat in private. I placed the leash on the rack by the door and went to the car and waited for almost an hour. Mistress Ann came to the car carrying a large bag, full of the items we had looked at. I was confused as neither one of us had that kind of money. She told me that Mistress Rebecca was wonderful and very generous. She explained that Mistress Rebecca had told her that she had been half tempted to put a collar on me the first time I visited the store, referring to me as a stray puppy dog in need of a Mistress. Anyway, she was so interested in my training with Mistress Ann, that she had given her all the items, but with a condition, that we come back each week and bring Polaroid pictures of my training. I was a little freaked to say the least, but Mistress Ann was in charge. She made me drive to Walmart on the way back to her place and buy several packages of Polaroid film.
We spent the next week playing with the lube and plugs and occasionally taking a picture for Mistress Rebecca. My ass was so tight we almost gave up on the medium plug. Finally when we had it half way in, Mistress Ann had an idea. She had me get on my knees and bend over in front of her while she sat in a chair. She placed her sexy foot on my butt cheek and then slid it over the base of the plug. She slowly undulated the plug back and forth while I knelt helplessly in front of her. I could feel it burn each time she put pressure on it. She worked it for a few minutes and then without warning gave a hard shove with her foot sinking the plug to the hilt. I gasp and thought I was going to pass out. I heard the click of the camera behind me and the whir of the motor ejecting the picture. She made me keep it in for a long time to help stretch my ass, but rewarded me with sex. She used the restraints and secured me to the bed, face up, and then straddled my cock. It was a unique feeling having my ass filled with the plug and having her silky smooth pussy sliding up and down my cock. It didn't take long for me to cum. Pretty soon I was tugging at my restraints as the orgasm took over my body. Given the intensity of the orgasm, I was sure that I must have shot a gallon of cum inside of her, but in reality it wasn't a gallon, but was a significant load as I was about to find out. She spun around facing my feet and scooter back over my face, and cupping her pussy lips with one hand. She lowered her sex to my face and told me it was time for dessert. She removed her hand and a large drip of cum from her pussy into my open mouth. She told me to lick it all up, but not to swallow it yet. My mouth was soon full of my seed. She scooted back so she could see my mouth and told me to show her the cum. As in presented my cum filled mouth, I heard another click of the camera and whir of the picture coming out. She then told me to swallow it and open my mouth. It was a lot and wasn't too bad. She had me drinking pineapple juice all week and told me that it was supposed to make my cum taste better. She was right. I opened my now empty mouth and another picture.
We now had quite the collection of pictures, but hadn't tried the strapon yet, but we had made good progress over the week. We drove back to the adult novelty shop to present Mistress Rebecca with our photo collection. We entered the store and Mistress Ann clipped on a leash and walked me over to the counter. Mistress Ann asked me if I had anything to give Mistress Rebecca and I replied, " Yes Ma'am," and handed Mistress Rebecca a very thick envelope of pictures. To my embarrassment she proceeded to look at each one and place them on the counter. Luckily there were no other customers in the store. She was pleased with the training but had hoped to see that strapon in my ass. Mistress Ann sent me to the car to wait while she and Mistress Rebecca had another long conversation.
Back at Mistress Ann's apartment, I had finally become comfortable with the medium plug, so it was now time for the strapon. Mistress Ann looked incredibly sexy wearing the strapon and harness. She had me in a doggy position, the plug still in my ass as she lubed her cock. She asked me if I was ready to be her bitch. I bit upper lip and said Yes. She removed the plug and placed the tip of her cock against my anus. A click of the camera and then pressure as she began pushing the cock into me, taking more pictures as she made forward process. I won't lie, it did hurt for a while, but she was patient and allowed me to get accustomed to it, then gave me more until she was balls deep and another picture. She grabbed my hips and began working the cock slowly in and out of my ass. I moaned like a slut in a porno. She stopped and gently slid the cock out of my ass. My ass had been so full and it now felt empty. She then had me lay on my back and then raised my legs and took aim for my exposed asshole. This time it slid in much more easily and soon I had my legs wrapped around her as she plundered my ass with her cock and my mouth with her tongue. She really meant it when she said I was going to be her bitch. She was ravaging me and she was loving it and so was I, and of course with that much excitement and stimulation, I was cummings all over our stomachs. She gave an evil grin, grabbed the camera and started taking more pictures with her cock in me and of her feeding me my cum with her fingers. I'm not one to be selfish when it comes to orgasms, and asked her to sit on my face. She was soon cumming almost as hard as I had just done. It was an amazing night and so were the evenings the rest of the week. She even had me practice sucking the strapon. My mouth is small, so I was having a hard time, but she made me practice while keeping a plug in my ass. One evening she made me jerk off into a small cup then give her strapon a blowjob. She told me she was going to cum in my mouth and told me to open wide. She poured my cum into my mouth, placed the head of the cock to my mouth and took a picture before pushing the cock in my mouth and telling me to swallow it and lick it clean. It was difficult swallowing with the cock my mouth, but I was up for the challenge.
After an amazingly kinky week, we headed back to see Mistress Rebecca with another envelope stuffed full of photos. Mistress Rebecca was overwhelming pleased with the pictures and my training, and even slipped her hand between her legs as she slowly savored each picture. I was sent to the car again and they had another long conversation. I didn't known what was said until later, but I will go ahead and fill you in. Mistress Rebecca loved the pictures of me taking my Mistresses' cock and complemented us both on how sexy we were. Mistress Rebecca said that she thought I would look even sexier taking a real cock. She explained that she had a male pet that could make that happen if Mistress Ann so desired. There was always an catch to Mistress Rebecca's offers. This one was a doosey. If this were to happen, she wanted both Mistress Ann and I to be their pets for the evening. She had given Mistress Ann a lot to consider and the next week was again filled with me taking her cock in my mouth and ass, but she kept teasing me, asking me, "I bet you wish that was a real cock, don't you?" She would keep at it until I said yes. We did take pictures, but this week many of them were of Mistress Ann's body, including of me giving her a creampie and eating it.
Another week and another trip to see Mistress Rebecca with pictures. Mistress Rebecca was quite pleased and especially enjoyed the pictures of Mistress Ann. I went to the car as usual and waited for my Mistress to return. When she returned, she had a small bag, a gift from Mistress Rebecca, and said that we were going spend the night at a nearby hotel. That worked for me, because I was ready for some kinky fun. I hadn't noticed that she had put our bag of toys in the car before we left her place. We got to the hotel and checked it. She told me that she needed to make a call and for me to get a shower. I hurried up and then waited for her to take her shower. After she dried off, she pulled out the bag of toys and dumped em on the spare bed. She grabbed the medium butt plug and lube and proceeded to use them to fill my ass. Then she opened up the small bag she got from Mistress Rebecca's shop and pulled out two pair of thigh high dark stockings. She said that Mistress Rebecca wanted pictures of us both in stockings. We both slipped on the stockings. She looked supper sexy, and I have to admit, they felt pretty good on my legs too. She opted for a little light bondage and tied my hands behind my back and she had me kneel on the floor. She stood before me, turned and offered me her beautiful ass. I worshipped her ass for several minutes and then came the knock at the door. I wasn't sure what was up, especially when she walked to the door and began to open it with both of us in the room naked. To my surprise in walked Mistress Rebecca, followed by a younger good looking guy who she introduced as her pet Ray. I didn't know what was going on and then Mistress Rebecca pulled out a collar and put it on Mistress Anne's neck. Mistress Ann, now pet Ann knelt next to me and told me that we would be their pets for the night. I was about to freak out, but Ann reached over and took hold of my cock and began to fondle it, making me horny and compliant. We watched as Mistress Rebecca and her pet Ray stripped. They both had attractive bodies. Mistress Rebecca walked pet Ray over to where we were kneeling, his hard cock jutting out in front of us. Ann took the lead and began fondling his cock and giving it little kisses. She looked so sexy playing wit his cock. In was in a daze, not realizing that she was also pulling me toward her and Ray's cock. She told me to kiss her and I did. She held our lips together and then guided Ray's cock between them. I now realized the reason for the blowjob training. This was what she wanted. I wasn't really attracted to guys, but wanted to make her happy and let my training take over, making Ray moan as my mouth played with his cock. Mistress Rebecca came over and took Ann by the hand and lead her to the bed. Mistress Rebecca sat on the bed and hard Ann sit in her lap. The two watched me suck my first real cock while Mistress Rebecca's hands explored Ann's body as she kissed her neck. This went on for several minutes and my jaw was getting sore. Ray lifted me to my feet and placed me face down over the edge of the bed, my hands still tied behind my back. The ladies came over for a closer look and to help lube my ass. They sat on either side of me and spread my ass cheeks to give Ray an easy target. I heard Ray putting on a rubber and knew I was about to become his bitch with my Mistress and her Mistress friend as an audience. He positioned the head of his cock against my ass. During strapon training I found that it went in easier if I rocked back on the cock and soon found myself rocking back onto his cock, feeling the head pop inside of me. It burned a bit at first, but subsided and I rocked back again and again. The Mistress watched as his entire cock sank into my ass and I heard the familiar sound of picture being taken. Once all the way in, he grabbed my hips like Ann had done before and began slowly breeding my ass, then building with speed and force. I moaned as he made me his bitch. He was close to cumming. He pulled out, turned me over, removed the condom. He straddled my chest and put his cock in my mouth. A few more strokes and he was filling my mouth with his cum. The ladies squealed in excitement and told me to swallow it, and I did, taking pictures of my submission. That was all Mistress Rebecca could take. She needed relief and told Ann to lay on the bed. Mistress Rebecca straddled Anne's face and ordered her to eat her. I still had not cum and this was so freaking sexy. You wouldn't have known that Ann had never eaten pussy before, but Mistress Rebecca in no time was cumming in her mouth. Both Ray and I were hard from watching the ladies. Mistress Rebecca fell back on the bed leaving Ann's face dripping wet. Ann's pussy was also dripping wet. Mistress Rebecca offered Ann to Ray. Ray first layer me on my back and then brought Ann over and placed her over me in a 69 position. He then went behind her and lined up her pussy with his cock. I watched inches away as it sank in, like a hot knife through soft butter. In no time he was balls deep in her sweet pussy, no condom. He then proceeded to breed her, his cock slamming into her just above my face and the sounds of sex ringing in my ears. I felt her lips on my cock and as his thrusts sped up,the faster she sucked until we all came together. Ray's cock began to soften and s!upper out of Ann. She lowered her pussy onto my face and served me the first creampie from another guy. When I had finished she spun around and held me close, kissing me deeply as I realized she was feeding me my own cum.
That was a night to remember and there were more, but I think this story is long enough..... The End..for now. Perhaps another later about when Mistress Ann sent me to stay with Mistress Rebecca and Ray for the weekend! I'm horny just recalling it.
