Date: Wed, 26 Jul 2000 00:01:42 GMT From: Sean Stevens <spankguy@hotmail.com> Subject: Jockstrapped Houseboy We had chatted a few times online and the invitation to commit to being his weekend erotic houseboy was intriguing. I had never done anything like this though the idea of being 'employed' in such a manner in which I would do as told, dress in accordance to his orders, and accept appropriate discipline when I failed to perform to expectation was a secret fantasy. A little about me, I'm 34, 5'9", 160, 32w, short dark blond buzz cut, clean shaven, worked out and in good shape, smooth with exception to chest and trail downward. I've got very muscular legs and what I've been told a very spankable ass. I tend to top though that's only because I find so few tops older then me who have the dominant attitude and look that attracts me. He described himself as a very dominant, in control, mid 50's, height/weight proportionate, strict, no non-sense, creative top. He lived a lone in home with an enclosed yard, pool and spa. The pic he sent along with the first email confirmed his stats and general appearance, I replied with my pic and confirmed mutual interest/attraction and set a date for my first weekend to be in service as his houseboy. Two days prior to the agreed upon weekend, I received an email that stated the following: boy, You are to arrive no later then 8:30 PM, wearing loose cotton gym shorts, tank top, sock, boots. Along with your basic toiletries you are to bring with you one pair of khaki shorts, short sleeve polo shirt, change of socks and an old worn jockstrap. Upon arrival you will be subjected to a through physical inspection and will be expected to sign off on a contract that will commit you to serving me as my personal erotic houseboy with the following rules: * I am to be addressed as Sir at all times. * You will do as told and speak when spoken to. * You will be dressed in a jockstrap and boots or less at all times while on the property. * When outside you will be nude. * You are not to touch your cock, balls, nipples or ass at anytime. * You are not to close any doors behind you at anytime, including the bathroom. * You will complete all chores/projects willingly and in the time framed given. * You will not cum without permission and you will refrain from cumming two days prior to arrival for service. * You will accept discipline as I deem necessary and appropriate. You will reply and confirm if these conditions are understood and acceptable, and I shall see you at 8:30 PM on Friday. - Sir When I finished reading the email I realized that I was hard with a growing wet spot on my shorts, apparently this was going to be an interesting weekend. Though one request had me concerned - the reference to bringing an old jock. The idea of being dressed in nothing more then a jock and boots all weekend sounded great, though I only jock I owned was two months old and hardly worn. Though it occurred to me that a neighbor friend had mentioned a leather store in the neighborhood that he had recently bought a pair of chaps from that sold used jocks. The following afternoon I went in search of this store and sure enough, they had a box full of used jocks at $5 a piece. The store's owner claimed that they were from the police academy, which I found amusing though hard to believe. I found three jocks that looked like they might fit and asked to try them on. I was directed to a small changing room in the back with a curtain that barely covered 3/4 of the doorway. I stripped and tried on the first jock though it was quickly apparent that the waistband was too loose. The second jock I tried on was a perfect fit. I had made a point to wear the boots that I'd be wearing as part of the requested uniform and was hoping to get a glimpse of myself in a mirror, though none was located in the changing room. I noticed that the storeowner was watching me though the gap in the curtain and stated, "the mirror is out here if you want to see how it looks on ya." Figuring that I had better get used to being dressed accordingly I stepped out to where the mirror was located The storeowner complemented me and while I tend not to be an egotiscial a-gay type, damn I looked good. There is nothing like the way a jock frames a butt just right and the pouch on this was just worn enough to offer a perfect outline trace of my semi-hard cock and cockhead. As I returned to the dressing room the storeowner followed inquiring if I needed the jock for any particular reason. As I pulled down the jock and stood buck naked with a semi hard-on I commented that I needed it for a job I had in the desert over the weekend. He grinned and commented that it must be an interesting job. I confirmed and paid the $5 bucks. That night I again stripped down and wore just the jock and boots while I packed the few things that I had been told to bring. While in the bathroom I caught a quick glimpse of myself in the full length mirror. Not only did the jock show the outline of my cock but was also semi transparent and you could clearly see the placement of my balls and cock in the upward position. Thank god it would only be me and Sir involved in this weekend scene as the jock offered little coverage. I next stripped down, grabbed a pair of clippers to give myself a quick pubic trim and jumped in the shower for a 'deep' cleaning and ball shave. I was hard the entire time though dared not even touch myself given the rules that I not cum two days prior to the weekend. The next day to say that I was distracted at my boring job was an understatement. I left as soon as I could knowing that it would be a 2 1/2 + hour drive to the desert depending on traffic and assumed that arriving late would be a bad way to start the weekend. I changed into my boots, shorts and tank top in the car and headed for my first weekend as a houseboy. Fortunately traffic was light and I arrived with enough time to stop at one of the local boy bars for a beer and a quick freshen up in the bathroom. The beer was a needed relief to calm the nervous excitement I was experiencing. At 8:30 PM I pulled up in front of my hosts most impressive house, I grabbed my bag and proceeded to the front door. On the door there was an envelope with 'boy' written on it, inside was a note that stated: "boy - you are late. Ring the door bell, wait two minutes then enter, close the door behind you and strip to your boots immediately, leave your clothes and personal items with exception to the jock you brought in the entry way. Proceed to the living room to your right, wait for me in the middle of the room in the inspection posture (standing, feet shoulder width apart, hands clasped behind your neck, eyes down). " I did as the note stated. I stood in the living room for a good 5 minutes before I heard a noise come from a side hallway, it was Sir. I was greeted though only able to see him from the shoulders down as I dare not raise my eyes to meets his. Standing naked, hands behind my neck, pits out, balls hanging in front of my employer to be for the next 2 two days had me nervous and excited at the same time, my semi hard cock had already begun dripping precum and gave away my true reaction to the circumstance. Sir proceeded to give me a complete inspection, grabbing, pinching slapping, twisting, probing every inch of my body. Sir then brought over a copy of an agreement that referenced all previous conditions, rules and expectations for the weekend and had me sign it and then posted it on the refrigerator door. Next it was confirmed that I had arrived late and must suffer the consequences as well as experience the seriousness of punishment that would be involved during the weekend whenever my actions did not live up to expectation. Sir sat down on the couch and pull me over his knee, legs spread. The bare handed swats started out slow and methodical though quickly increased the in rhythm and intensity until each swat left a biting sting. Around the 50th swat I could only imagine how red my butt must be and found myself sweating, moaning and squirming. Finally I was told that this punishment session was complete and directed off Sirs knee, however pushed to my knees, hands behind my back and informed that this position was 'on knees.' Next Sir stood up in front of me, pulled out his semi erect cock and told me to get it hard. Without thinking I took him into my mouth and within seconds it seemed to swell to what I would guess to be 8 inches and fat. Sir proceed to pump his meat in my mouth, balls slapping against my chin, pubic bush in my nose, occasionally thrusting all the way in to confirm my deep throat abilities. Sir was most complementary and indicated how much he was looking forward to having my complete attention all weekend. He also mentioned a few surprises that he was certain I would enjoy. Sir soon tensed and pulled out just in time to shoot his load on my chest though cautioned me against wiping it off, choosing instead to rub it into my chest hair. I was told to grab two beers from the refrigerator and given a short tour of the property. Sir was semi retired and doing very well financially. His home had three spacious bedrooms and a large enclosed yard and pool/spa. I was shown the room that I would be using and it was again confirmed that at no time was I allowed to close any doors behind me, i.e. no privacy. We next headed outside to enjoy the warm desert evening, chat a bit and enjoy the spa. Sir was extremely attractive, in good shape for his age and he seemed equally happy with my looks and build. This was going to be a most interesting weekend. After soaking in the spa for 20 minutes or so, the doorbell rang. Sir commented that it must be the pizza he ordered and instructed me to grab the $20 on the table and answer the door. I jumped out of the spa, quickly dried off, wrapped the towel around me and headed inside. Sir called me back and reminded me that all I was to be wearing indoors was a jock. I couldn't believe it, did he really expect me to answer the door in just a jockstrap? With an evil grin he confirm this question. I pulled on the jock, grabbed the $20 and headed to the front door. I opened the door and standing there was a young college guy, maybe around 21 or 22, presumably straight, good looking but sort of geekly in his pizza delivery uniform. He snickered in response to my apparent state of undress, gave me the pizza, took the $20 and stated, 'nice jock' before he turned and walked toward his car. I turned back into the house and caught a glimpse of myself in a full-length wall mirror only to realize that I apparently had not dried off completely as the jock pouch was wet and completely transparent. There was no question of a doubt that the pizza boy could see my cock, balls and pubic bush through the worn wet fabric. I was completely humiliated. Sir and I enjoyed the pizza and continued conversation. As it was getting late Sir told me to clean up and meet him in the master bedroom. I did as told. Sir was lying nude on his bed, face down, with a bottle of massage oil on the nightstand. I was instructed to give him a full body to body massage. I poured a generous amount of oil across his back and down my chest and proceed to slide up and down, from his butt to shoulders, slowly working the tension out of Sir's muscles. Just when I thought he as ready to nod off he slid me on to my stomach, spread my cheeks and slid his 8 inches up my hole and proceeded to enjoy this houseboy's butt. When he was finished, he took me over his knee one last time for a bedtime spanking, which consisted of 20 swats, the last 5 being real stingers. I was then sent to my room, red butt, rock hard and dripping, and no permission to get off. I found a note on my bed that indicated that my alarm was set to wake me up at the appropriate time, make coffee and bring it into Sir, crawl under the covers, take his soft cock into my mouth and wake him up accordingly. I crawled into bed, exhausted and horny. At 7:30 AM the alarm went off, I rolled out of bed, headed for the kitchen, got the coffee machine going the proceeded outside to the pool to do some early morning stretching, nude of course. It felt great to be in the already warm morning desert air. I also slipped into the pool and did a few laps before drying off and taking coffee to Sir. As ordered I slipped under his sheets and took is soft cock into my mouth. There is nothing more delicious then taking a soft cock into your mouth and gently rolling it around until it starts to stir just a bit. It took on a semi hard state and Sir started to wake, took hold of the back of my head and started working the motion to his liking. Just as he was about to cum, he pulled his cock out of my mouth and aim is load at my lower stomach and shot the load right into my pubes. He ordered me to remain on his bed, not to clean up at all and proceeded to the bathroom where he showered and clean up. Upon his return I was told to stand up and take the inspection stance. I did as told, feet shoulder width apart, hands clasped behind my neck, eyes down. I was told that as I had performed so well thus far that I was going to be taken to breakfast at Sir's favorite hangout. I was sent into my room and told to dress in the cotton shorts, tank top and sneakers that I had arrived wearing. I joined Sir in the kitchen at which time I was informed that I had not cleaned up the coffeepot and would have to be punished. I was led into the living room, my shorts were pulled down to my ankles and told to spread my cheeks. I then felt a butt plug pushing against my tight hole, as it had been lubed generously a good push and all 5 inches of it slipped right in. I moaned at the intrusion, and my cock bounced at the added stimulation. I was then bent over, hand on my thighs and Sir proceeded to give me 20 quick hard swats with what felt like a ping pong paddle. My butt was on fire when he was done. My shorts were pulled up and we were off to breakfast, Sir dressed in khaki shorts and a polo and his weekend houseboy, dried cum on his pubes, plugged, and freshly spanked wearing only a pair of loose cotton shorts and a tank top. My cock was barely concealed, esp. in it's semi erect state, I did my best to cover it with the tank top, though Sir was on to my plan and told me to tuck my shirt in. We arrived at his favorite breakfast hangout. There were a handful of older gentleman eating in the booths, Sir apparently knew a few and wave hello. All took notice of me and the way I was dressed. The waitress took Sir's order and then indicated that 'the boy will have the breakfast special.' The waitress smirked in my direction and then left the table. Sir then pulled out of his pocket what appeared to be a leather cuff and leash attachment. He told be to take it into the bathroom, place the cuff around my balls and allow the leash to lead out through my shorts left leg. I did as told and when I return to the table he quickly took hold of the leash and began pulling on it causing my balls to stretch away from my body. This amused Sir considerably. Soon there after a friend of his approached the table and was invited to join us. I was introduced as 'the boy;' and for the most part left out of the conversation until there was a mention of a dinner party and whether or not I would be there, which Sir confirmed. We all finished our meals, which was difficult at times for me as Sir seemed amused at pulling on the leash just when I would start to drink my coffee. Sir and his friend said their good-byes and we departed. On the way home we stopped at the supermarket and I was told to shop for a dinner party of 6, make it a bbq, keep it simple, and dessert was to include whip cream. I shopped accordingly and we returned to the house. When we returned to the house I was reminded that I was only to be wearing a jock and boots. I immediately stripped and proceeded to put the food away in the kitchen. Sir then called me into the living room, inspection stance. I reported as ordered and informed of the plan for the day. I was to clean the kitchen, guest bathroom, mow the back yard grass, clean the pool and surrounding patio area, prep the food and only after that would I be allowed to sun by the pool before the guests arrived at 7:00 PM. Sir then bent me over and gave me 10 hard slaps just to bring my cheeks back to a glowing red and reminder of what I could expect if I didn't do a excellent job on all the assigned tasks. I got right on it and took care of things in the kitchen and bathrooms, and prepped the dinner. I then joined Sir outside where he was lounging in the shade reading a book. I had to be reminded that when outside I was to strip out of the jock which resulted in 10 swats before I started on the yard. Given it was mid afternoon at this point the temps were hitting close to 105 degrees and it didn't take long to work up a real sweat. When Sir noticed me eyeing the pool he jumped in and ordered me to get him a beer, though no invite to join him was included. Having not cum in three days, my balls were full, my cock was semi hard and I was working out in the yard, nude, sweaty and about as horny as I could ever remember. When I was finally done with assigned projects Sir called me to the center of the yard and inspection stance. I was sweating pretty hard and looking forward to cooling down in the pool. Sir confirmed that a good job had been done in all assigned areas and that I would next be allowed to lounge by the pool though first I should be cleaned up before entering the pool. He led me to a walkway behind the garage where he had a large pail and instructed me to get in on all fours. Sir hosed me down with a garden hose and squirted some dish washing liquid on me and proceeded to wash me like you would with a pet dog, taking special attention to my backside, cock and balls. I was humiliated being treated as such however the opportunity to cool down was more then appreciated. For the next few hours I was permitted to lounge and float in the pool soaking in the hot desert sun. Sir and I chatted a bit, drank a few beers and enjoyed the afternoon. At 6:00 PM was told to take a shower and prepare for the dinner party. Sir called me into the living room, inspection stance. I was inspected and spanked, bent over and plugged, told to address all guests as Sir, make sure everyone's cocktails were kept full and dinner was to be served at 8:30. I was then sent to the kitchen to set up the bar. A few minutes later the doorbell rang and Sir told me to let answer the door. I panicked for a minute, thinking that he didn't expect me to open the door to total strangers dressed only in a jockstrap and boots. Apparently he did and gave my butt a hard swat as I passed by him after the bell rang for a second time. I open the door to two older gentlemen, their eyes almost popped out of their head and their eyes went straight to my jock pouch. It was then that I guessed that none of the guests were warned of my presence. I welcomed them in, showed them to the patio and took their drink orders all the while feeling totally exposed given their apparent glances at my pouch and backside. As I left for the kitchen I over heard one of the guests say something to Sir and they all broke into laughter, I could only assume that the comment in some way related to me and what was to come. In the course of the next hour additional guests arrived, all equally surprised when I answered the door, most in their mid 50's and 60's, well to do and amused at the idea of there being a boy dressed only in a jock serving them. I got the bbq going and started cooking the chicken, while prepping the side dishes Sir called me out and verbally chastised me for allowing one of the guest's cocktails to run dry. I apologized and returned to the kitchen to refresh the glass. Sir followed me and order me to grab ankles and gave my butt 10 quick swats for punishment. He made them loud and clearly so his guests could hear what was happening through the open window. When I returned with the refreshed cocktail, the guest commented to Sir about my red butt. Sir commented that the boy occasionally needed to be kept in line and reminded of his responsibilities, and stated that if it happened again the punishment would not be done in private. At the moment I knew I was in trouble, though had to excuse myself and continue on with the prep of the meal. When all was ready I informed Sir and the guests that dinner was ready. Salad was served, followed by the bbq chicken and sides. For the most part everyone pretty much seemed to ignore me and enjoyed the meal and conversation amongst themselves. Occasionally when I would have to bend over next to a guest to serve wine or fill a glass of water they would take the opportunity to squeeze or pat my bare butt. When not busy with something to do I just stood off to the side, hands clasped behind my neck waiting. Eventually I cleared all the dishes and started to clean up the kitchen. I next prepared the fresh berries that were to be served with whip cream for dessert. Just then Sir walked into the kitchen, commented on how well everything was going then order me to drop the jock and remove the plug. I hesitated and he said, 'Do it, now.' He was going to have me serve the desert buck naked, balls hanging, and there was nothing I could do or say. I thought I was going to die of humiliation. He grabbed the whip cream and said follow me. I grabbed the dessert tray and follow, naked except for a pair of boots. A hush came over the conversation at the table when the guests realized that I had gone through a costume change so to speak, a few gasped and I heard an "oh my" and a 'very nice, though couldn't be certain who had made the comments. Sir's next surprise floored me. He told the guests that in addition to a squirt of whip cream on the berries, each guest would then get to choose a spot anywhere on the my body and then I would have to squirt the area with whip cream and the guest would then lick it off. The first guest smiled at me and pointed at the tip of mye now semi-hard cock. I looked at Sir pleading that this wasn't really going happen, his return glance was unquestioning. I squirted whip cream on my cock head and the guest quickly took it in his mouth and licked it clean, needless to say I was sporting a full hard on when he was done. The next guest licked the cream off my nipple. When all was said and done I had had whip cream licked my cock, balls, nipples, back and neck. Sir was last however and instructed me to turn around and grab ankles. The then placed the nozzle up against my exposed hole, pushed it in just a 1/2 inch or so and tipped the can, letting loose an explosion of whip cream up my rear. I jumped not expecting the pressure from the aerosol can which made guests roared with laughter. Sir licked my hole just a bit then sent me off to the side, indicating inspection stance, back to the guests. While they enjoyed their desserts I stood their totally humiliated, naked, hands clasped behind my neck and whip cream slowly melting and dripping down the back of my legs. Ten minutes later I was released to clear the dishes and finish the clean up, this time completely naked. A few of the guests took the opportunity to excuse themselves to use the rest room, first stopping in the kitchen to comment and commend me on the dinner, my body, and how much they were enjoying the evening. The dinner finally came to a close, a few of the guest made plans to meet at a local bar afterward. I showed everyone to the door one at a time encouraging everyone to drive safely. One guest commented that he wouldn't have had so much to drink had he not hoped to see my spanked in front of everyone. Hearing that, Sir, gave me the look, I turned, grabbed ankles and received 20 swats to the bare ass in front of the remaining guests. Sir indicated that I should remain bending over, legs spread, while he bid farewell to his guests . . . . . Sir returned, slapped my butt, told me to put on some clothes as the night was still young and that we were joining the guys at the bar. Later that night when we returned to the house Sir again helped himself to my butt and sent me to bed rock hard and dripping. The following morning he finally permitted me to j/o at which time I shot one of the biggest loads in my life, straight across my chest. Sir rubbed it in and sent me home promising a return visit if I was interested in again serving him as his houseboy. The above is a true experience which occurred last summer, and repeated this past May. If you have had a similar houseboy experiences and/or fantasies, or if you live in the LA area and this experience has caught your attention, please feel free to drop me a message at spankguy@hotmail.com