Tina and Rick Part 5 - Rick's Hooker
by Tina D firstname.lastname@example.org
After 2 years of living full time as a female, I really felt I had achieved the original goal set by the doctor who started me on female hormones. I am exactly 5 foot 7, with naturally very thick, wavy dark brunette hair (I don't care if gentlemen prefer blondes, I am staying brunette forever), brown eyes, and 131 pounds (I blame at least 2 pounds on my breast augmentation - DD). I lucked out and got my mother's very fine facial features. My male parts have shrunk (a lot) and are pretty easily hidden in nearly any bathing suit or lingerie I buy, but I wear tight fitting thong gaffs to make sure nothing shows, even during sex. When I am not exercising (I am obsessed with making my legs look "fuckable"), I still spend every waking hour in heels. Guys continue to hit on me frequently enough to make me feel as sexy as hell. Even though my doctor tells me that I have a lot of years of looking good ahead of me, I don't want to waste any in drab clothes. I don't wear anything unless I think it is sexy.
(And, as an aside, thank you Andy for the drawing you sent of me, which was very, very flattering!!! Since I was in that position, why didn't you join me in the drawing?)
Also, after 2 years of living as Rick's full time "sex slave," Rick decided we needed to spend some time apart. When I moved into my own apartment, I could still count on one hand the number of guys I had had sex with, or more correctly the number of guys I had made have orgasms. Well, not exactly one hand. I had never had sex with a woman or with another TG, but I had made 6 different men have orgasms. Yes, I am keeping count, and that is probably the little male part still left in my brain.
The first guy was about 25, and shot his load all over me when I gave him a handjob in the front seat of his car. His penis was also the first penis I ever had in my mouth, although he didn't cum in my mouth. The next guy I made cum, and who had cum in me and all over me at least a thousand times since, was Rick, who is now in his mid thirties. The third guy was Steve, a store owner that I still work for part time, who is in his mid 40's. The fourth guy was an old friend of Rick's, about 40, who stayed overnight at our place on a night that Rick got drunk and passed out. I had had just enough wine to make me want a penis in my mouth, and Rick's friend was only too glad to let me take advantage of the raging hardon he developed when I started squeezing his cock and telling him I desperately needed to drink some cum. The fifth and sixth guys were about my age, maybe 20 or 21, and I spent a couple hours at their place after they changed a flat tire on my car on a very dark, very rainy night. Nothing says thank you like a super hot blow job, and my little mouth took turns clamping onto their cocks and thanked one of them twice and the other three times before I left for home.
Living alone in my apartment hasn't changed my sex life a lot. Rick calls occasionally to tell me he has to come over and "do me" before his balls explode, and judging by the size of some of his recent cumloads, he is usually telling the truth. Steve considers me to be his girlfriend, although I am not as attracted to him as I am to Rick, and we have sex a couple of times a week. Steve thinks I am not as attracted to him as he is 25 years older than me, but the age difference doesn't actually matter to me at all. Steve now knows I am a TG, which means he has sex with me anywhere he wants now, and not just with my hands, mouth or tits. While Rick still likes to stick my legs up in the air and almost violently fuck me from the front, Steve prefers to take me slowly and gently, spoon-style or doggystyle from behind. They both know that my absolute favorite thing to do is suck cock, and neither one of them objects to being on the receiving end of one of my expert blowjobs. They have both seen pictures of me having various kinds of sex with the other, and Rick gets especially turned on by pictures of me sucking on Steve's cock.
In the middle of the winter, Rick asked me if I wanted to spend 4 days on vacation with him. He agreed to pay all the bills, and I agreed to go with him. He was totally honest, and admitted he wanted a total sex vacation, and a chance to work on some sex fantasies with me. He told me we could talk about some of his fantasies on the road. All I needed to do was pack a couple of suitcases with ultra sexy clothes, shoes and lingerie, and leave the driving and arrangements up to Rick. We could leave in the middle of the next week, and that is exactly what we did.
Rick opened up to me about his latest fantasies during the 10 hour drive to our destination, and he simply took it for granted that I would go along with whatever he said. I had never told Rick "no," and nothing he said ever surprised me. Rick is a sex addict, and I am a total cum addict, and Rick has tried a little bit of everything, and a lot of some things with me in the past. We were going to be staying at a big, first class hotel and Rick was hoping to play out a different fantasy every night. He did leave out a couple of important details, but I found out how very real his fantasies were on our very first night at the hotel.
We arrived at the hotel at supper time, after a long day of driving. We were both as horny as possible when we arrived. We had literally just walked into the room and Rick had already pulled his cock out of his pants. His pointed his big, hard erection straight at me and he was already asking for a blowjob. Being totally addicted to both his cock and his cum, I wanted more than anything to drop on my knees and suck him off, but I resisted the temptation and looked him square in the eye and said, "You'll have to find someone you can pay to do that sort of thing." It was the first time I had ever refused to grant Rick a sexual favor the instant he requested it.
Rick slipped into a track suit and ordered a pizza. Soon, he was settled in front of the television with his cheese and pepperoni. Not wanting even an extra ounce on my body tonight, I picked some clothes out of a suitcase and headed for the bathroom. After a long shower, I dried my hair and then sat in front of the mirror and did most of my makeup. And now time to get dressed! I had picked out one of the skimpiest, sluttiest outfits I had ever dared to wear in public, but my heart was already thumping with anticipation at the responses I knew I would get when I walked out of the hotel room all by myself. With the first step completed, I looked myself over from every angle in the bathroom mirror. Perfect. Every smooth, shapely inch of my body was now encased in a tight black body stocking with open busts and a "convenience crotch." I could already feel myself breathing harder as I checked out my very full tits and perfectly rounded ass in the mirror. I still marvel at the incredibly shapely body that looks back at me from the mirror.
And next the tight black spandex thong that made me look totally female, doing an excellent job of smoothing and outlining the path running from my wide hips down to the space between the tops of my shapely thighs. In back, the tight spandex thong did a wonderful job of highlighting the crack between the rounded halves of my ass. At this point, I knew that if Rick could see me now, I would not make it out of the hotel room until he filled me with a week's worth of sperm, and so I double checked to make sure that the bathroom door was locked. While I desperately wanted to feel Rick's cock filling me and his semen running inside me, I also wanted to enjoy strutting out on my own for a little while tonight, in the hopes of maybe getting a glance, a whistle, or maybe even a free drink (one of the best things about being a girl, by the way, is finding out that men will pay for all of your drinks if they think they have even a remote chance of getting any sexual favors from you).
I was not finished dressing and it wasn't time to put on my shoes, but I was already feeling totally slutty and I couldn't resist slipping my feet into my latest pair of "sex shoes." These were black leather pumps with 4.5 inch stiletto heels and two thick ankle straps. I could wear them fairly comfortably because I spend so much time in high heels. Very, very sexy. A step beyond the usual "cum-fuck-me-boys" shoes guys love, these were the "cum-fuck-me-and-shoot-cum-all-over-every-square-inch-of-my-body-right-now" shoes that guys fantasize about their girlfriends wearing during sex. Rick loved any heels that strapped onto my ankles, because they were impossible to knock off during sex, no matter how hard he pumped into me and no matter what position he put me in when he was pumping me full of cum. Rick was already knocking on the bathroom door, "Come on, baby, please let me have a peak!"
"No way honey! You'll have to pay if you want to get a look at this!" Rick knew the drill, this was his fantasy. He scratched a bit on the door and then headed back for more pizza and television. And now the hardest part. Slipping into a skin-tight, jet black halter top mini-dress with a built in bra that pushed my boobs up and much closer together. Since getting my boob job, I never go braless unless I am in bed or in the shower! This was only the second time I had tried this dress on, and having just lost 2 pounds (and believe me, they weren't extra pounds), and having skipped pizza, and being cased totally in nylon helped me slip into the the super tight little shimmy dress, and every curve fell perfectly into place. I am always my biggest critic, and as I looked into the mirror, I could see that the dress was just a bit too short, a smidge too tight, and exaggerated my cleavage way too much to be confused with the average cocktail dress that a wife or girlfriend might wear. The girl looking back at me from the mirror had to be a hooker!
In a few more minutes, I finished the final touches on my makeup. I purposely went a bit too heavy on the eye shadow and mascara for a wife or girlfriend. I outlined my lips with a dark red pencil and ultra-shine lipstick, hoping for that pouty look that would turn my mouth into an open invitation for fun and games to every red-blooded man I would meet tonight. It was after 9 p.m., and although there was no window in the bathroom, I knew it was already dark outside. I was really proud of the effect the outfit and makeup had achieved. My dark brunette hair was full and flowing in thick sexy waves around my neck and shoulders, and the night time shadows would highlight my cleavage. Rick's insistence that I get DD implants had pretty much assured that my cleavage didn't need a lot of highlighting on my small frame, but I would take all the help I could get.
I knocked on the inside of the bathroom door and slowly opened the door and peaked out. I told Rick not to peak and he dutifully rolled over in the far bed. As he rolled over, I slipped out of the bathroom, grabbed my very slinky short faux mink jacket, my handbag with cash, condoms, lube, lipstick, hairbrush, room access card, and cell phone, and headed out the door without Rick seeing me or my outfit. I took a quick glance at myself in the full length mirror near the door. I admitted to myself that I was a knockout, but a knockout who definitely looked like a high priced hooker.
Now, here I was walking along the corridor of a very expensive hotel equipped with cameras in every hallway, stairwell, corridor and elevator, at one of the busiest times of year, on a busy Thursday night, dressed as a hooker, albeit an expensive looking hooker. I had a pretty good instinct for dressing and acting like a hooker, and recalled that I had been dressed as a hooker during my first two sexual encounters, with two different guys, about 2 years earlier. On more than one occasion when I had been dressed as a hooker when Rick and I used to live together, Rick had nearly nearly fucked me to death, and I was expecting him to impale me with his usual raging hardon tonight and deposit about half a dozen loads of cum into me during a fuckathon that would last long into the night.
As I got off of the elevator on the main floor, I started walking along one of the wide corridors that had a number of specialty shops and tiny cafes, a few of which were still open. As I walked along by myself, I could already see a few men glancing, and a few others staring. On the other side of the hallway, a wife, or girlfriend, hit her man on the shoulder as he let his eyes wander over my body just a little too long. I was taking my time, strolling along and looking through shop windows, knowing that it would be a little while before Rick came down from the room, looking for a hooker for hire. The plan was for me to go and wait for him in the hotel bar, and maybe even get lucky and have someone buy me a drink. Rick would see me in the bar and pretend not to know me. He would then hire me to join him in his room and entertain him sexually.
Although I felt terribly excited inside, I didn't feel any of the nervousness I used to feel when I went out in public like this. Of course, that was before I had lived as a woman non-stop for 2 years, with a heterosexual male lover with an insatiable appetite for a variety of sexual activities. It was before I had completed 2 years of female hormone therapy, and before I had undergone 3 feminizing surgeries. It was before my affair with a well-to-do store owner had made it possible for me to easily afford a nice apartment while working only part time. It was before the rainy night that I sucked off two guys at the same time. So here I was, very sexually aroused, but not nervous. On the prowl in the hopes that I could get some men to take some second glances at me before Rick arrived to hire me for the night.
And then I realized I had a problem. I was supposed to head into the bar dressed as a hooker, and Rick was supposed to come into the bar and hire me. After that, I knew things would get really simple. Rick would take me back to the room, romance me for about a minute, drive his cock into me, and fuck my brains out while I clung to the bed for dear life, as had happened many times before. But as I walked along the long corridor on this side of the hotel, I had already passed 2 bars. As I rounded the corner and headed down another corridor, there was a 3rd bar. The ground floor of the hotel was more like an exclusive little mall. I had expected that the hotel would have only one nightclub, but after I walked along a little further, and found a directory, I found that the hotel had at least 4 bars.
Not sure what to do, I thought about calling Rick with the cell phone, or possibly heading back to the room, which would totally spoil the fantasy for Rick, although I knew he would still get plenty of sex tonight. I started walking down a smaller middle corridor and found that it ran between two of the bars in the main corridors. I ducked into a washroom and took out my cell phone to call Rick. But then I made a different decision. I would simply sit on one of the couches in the corridors between shops and wait for Rick to find me and hire me for the night. With a plan in mind, I headed out the bathroom door.
I hadn't walked even 25 feet from the washroom door when two men talking together turned and asked me to join them in one of the bars. They both had drinks in hand, and pointed to where I had seen them sitting at the bar as I walked by just a few minutes ago. Evidently, they had seen me too. One was about 25, the other was about 45, and they were both very cute. I immediately forgot all about sitting on the couch by myself waiting for Rick, and agreed to join them. We moved around to the far side of the bar where we were able to find 3 stools together. My gentlemen friends carefully sat me down on the middle stool and as I unzipped and slipped out of my jacket, they very promptly ordered me a glass of my favorite, and expensive, white wine.
As my two new men friends started telling me about their business trips, comparing their new cars, asking if I approved of their latest CD purchases, and seeking my advice on the latest problems they had encountered on dates, I thought it would be fun to start counting how often they touched me. Bob was touching my head, neck and shoulders. Tom was going for my thigh and knee, and his touches were already turning into short little rubs. Although I hadn't finished the first glass, they had already signaled the bartender and another glass of cold white wine was waiting in front of me. They were encouraging me to drink up to catch up to them, so I did just that. As I was sipping on my second glass of wine and being as friendly and interested as possible, I noticed that Tom, the older of the two, was now keeping his free hand on my thigh. It turned out that Bob, the younger guy, worked for Tom. I kept looking around for Rick, who was nowhere in sight.
After listening to Tom tell me about how much money he had earned on his latest business deal, I reached out and squeezed his thigh not far from his crotch, and said, "That is so amazing, you are so lucky you can make money that way." He looked very pleased with himself as I slowly drew my hand back across his thigh. I was leaning towards Tom on my stool, letting him have a clear view of my cleavage, and at the same time touching his thigh. When Bob left for a washroom break, I ran a hand up Tom's inseem and found what I was pretty sure was the tip of his penis. I left my hand right where I had found him, for a few seconds, and then sat back upright on my stool. Tom's eyes looked like they were going to pop out of his head.
I was doing my best to send signals to Tom to let him know that I found him attractive. I was trying to thrust my breasts forward and, while I knew it was all in my imagination, my breasts felt like my dress was getting tighter and that my boobs were about to tear through the fabric. Tom was definitely picking up on the signals, but he was a bit slow to act. He ordered me a third glass of wine, and he finally stopped talking about money, cars and other recent purchases. Bob returned from the washroom and their conversation turned towards telling me how incredibly hot I looked, and how they had seen me walk past and because I was so hot looking it had given them the courage to come out and wait for me to ask me to join them in the bar and they didn't normally do things like this.
I was drinking my third glass of wine and needed to pee really badly. Tom offered to walk me to the washroom. Just before I stepped into the washroom, I asked Tom to join me on a couch in one of the sitting areas between shops, and I leaned towards him and slipped a hand into his crotch, found my target and started squeezing and rubbing his penis. There was no doubt about it, he had to be picking up on this signal and his penis was definitely getting hard inside his pants. I got up to head to the washroom and told Tom I would be right back. Tom told me to meet him back at the bar, and that he would go back and get rid of Bob. As Tom headed for the bar, and I headed for washroom, around the corner at the end of the corridor walked Rick.
Rick casually walked towards me and asked what was going on. I asked him where the hell he had been and why hadn't he phoned me. He said he had looked in on me a few times, and that I appeared to be having too good a time to disturb. "Call me and let me know which room he is taking you to," said Rick, and he walked off. I certainly hadn't planned on this! Heading for the washroom, a dozen thoughts ran through my head. And then I knew exactly what to do.
When I got back to the bar, Tom was by himself. After a minute of chit-chat, and a sip or two of wine, he asked me straight out, "What would it take to get you up to my room for a little while?" Thank goodness I had a plan. I told Tom that I had to see a regular client tonight, but that I could come up to his room and visit with him for just a short while. After finding out what room Tom was in, I slipped into the washroom again and called Rick to tell him which room we would be in. On the way to his room, Tom told me that he often visited town, and asked me if it would be possible to get on my regular client list. At this point, it was absolutely clear to me that Tom thought I was from an escort service. And this is when I really went for broke.
I told Tom, "I only see regular customers after my employer does a credit check on them. If I spend too much time with someone who can't afford me, I might lose a better paying regular customer."
Tom was rubbing my back and letting his hand slide down onto my ass as we walked along the corridor. "So, what do I have to do to become a regular customer?"
"Leave me a business card, and spend a bit of time with me tonight just talking."
"You mean, no sex tonight?"
"That's right, no sex tonight." At this point, I figured Tom would tell me to take a hike, and then he would go back to his room, flip through the phone book, and call an escort service to send someone to relieve his growing erection. But he didn't. Instead, he fished into his pocket, gave me a business card, took me by the hand, and headed me down the hall towards the elevator.
"OK, we'll talk tonight, but I want you to run that credit check on me and be back here tomorrow night!" said Tom. Evidently, he was the real deal, and he was seriously wanting to hire a regular private escort. I had no idea just how serious he was until I had spent some time in his room.
As soon as we got into his room, which was obviously one of the more expensive rooms in the hotel, Tom got busy about the business of turning on the television and ordering a bottle of wine. We left the lights down and only the television lit the room. A young man arrived from room service, opened the wine, poured us each a glass and left. Hoping that Rick was nearby, but actually feeling pretty safe with Tom, I said "Tom, I don't usually do this, but you are so nice." With that, I found some nice music on the television, and while Tom leaned back on the couch, I started dancing. I was playing with my hair and letting my body weave around like fluid and was loving every second of this. I pulled the spaghetti straps on my dress down over my shoulders and danced a few more minutes. And then I slowly began to slide out of my dress while I kept dancing. It wasn't easy because the dress was pretty tight, but the impact on Tom was immediate. Remember, the body stocking I was wearing had open breasts, so once I slipped out of my shimmy dress, my breasts were standing out in all their naked glory. Within seconds, Tom was up off the couch and fondling my breasts as I kept dancing.
I was now wearing only my body stocking, thong panties, and high heels. Tom was literally drooling on me as I took him by the hand and led him towards the bed. Once I had Tom sitting up in bed, I walked to the end of the bed and crawled up on all fours towards him. I pulled myself up and sat directly in front of him with my legs curled underneath me in the sexiest pose I know. Tom reached back and took out his wallet, and slid a couple of bills across the bed in front of me. I looked to see how much money he had just pushed towards me, and then did my best not to act surprised. I told Tom I would be right back. I got up, got a hot, wet washcloth from the bathroom, picked up my pocketbook and headed back to the bed where I slipped the bills into my pocketbook, unzipped Tom's pants, helped him slide out of them, and started washing his cock with the warm washcloth.
As I started fondling his cock, it was obvious that Tom enjoyed the feel of my hands. I slid a bit closer to Tom and kept fondling his cock. I used some lube on his cock and started to give him what I would call a fun, sweet, passionate handjob. As I kept rubbing him, I started squeezing him, doing my best to make Tom feel like his cock was inside someone's pussy or ass. While I kept up the handjob, Tom started fondling and kissing my tits, and then he started to do some serious sucking on my nipples.
I could tell by the way he was already moaning as I kept rubbing him that it was going to be really easy to make him cum. He was totally hypnotized by my tits. I rubbed him more slowly, wanting to make this last a bit longer for him. And then he took his mouth off of my nipples and reached back and pulled another bill out of his wallet and slid it across to me. I put this new bill in my pocketbook. I stood up off the bed, and pulled him over so his legs hung off the side of the bed. I kneeled between his knees and started alternately rubbing his cock with my hand and squeezing his cock between my big breasts. Each time I squeezed him into the crack between my breasts, I would spend a minute or two raising up and down on my knees so that I could fuck his cock with my tits.
Tom was groaning louder now, and each time I switched from handjob to titjob he would groan with approval to let me know he wanted a titjob more than he wanted a handjob. I was really trying not to let him cum yet. He was cupping my breasts and squeezing them together around his cock and he slid forward and started to shove his cock in and out between my breasts. He asked me to pretend my hands were tied together behind my back as he continued to titfuck me. He was fucking my tits harder and harder, and I knew he wanted to cum really badly. I started telling him to soak my tits with his cum, "Oh Baby, please shoot your load all over my big tits."
I was right in the middle of telling Tom what a beautiful stiff cock he had, and how much I was going to enjoy sucking him off tomorrow, when he stopped titfucking me, reached into his wallet and pulled out another bill. I slid this bill into my pocketbook and stood up, turned around and sat in his lap and rubbed my ass on his cock as he reached around and squeezed and fondled my boobs. At this point, I was absolutely certain that I could slip his cock past the thin strap in the back of my thong, and convince him that I was either letting him fuck me in the ass, or that I had a super tight pussy. But then he reached back and pulled another bill out of his wallet and tossed it on the floor beside my pocketbook. "Baby, please give me a blowjob!" Without any hesitation, I slid this bill into my pocketbook, and then felt around and pulled out a condom. I kneeled down and started kissing Tom's cock shaft and fondling his balls to make sure he was good and hard, and I tore open the condom wrapper. As I tore open the package Tom said, "Do you have to?'
"If you want to come in my little mouth I have to," I responded. I crawled back up onto the bed on all fours, and as Tom swung back onto the bed, I kneeled between his knees and rubbed his cock with my hands to make sure he was good and hard. I then slowly unrolled the condom onto his cock, making sure to squeeze every inch of his cock tightly as I unrolled the condom all the way down to the base of his cock. Once I had his cock snugly wrapped in a nice tight condom, I thought again about letting him fuck me. I was absolutely certain that he would not know. But Tom wanted a blowjob, and so my mouth dropped down onto his cock and I started giving him head for all I was worth. I had blown 5 guys before, and none had ever worn condoms when I blew them, and the feeling of having a slick lubricated condom covered cock in my mouth was making me totally horny. Tom was laying back helplessly and kept saying, over and over, "Oh fuck, oh fuck, this is incredible, oh fuck, oh fuck, I can't believe this, this is so incredible." I started out sucking him while I was on all fours, but then I lay down flat between his legs to get more comfortable as I continued blowing him. I didn't feel badly about the money, I knew I was very, very good at this, and that Tom was going to love every minute of it.
I could already feel the reservoir tip on the end of the condom starting to feel like a little inflated balloon as it gradually filled to capacity with Tom's pre-cum. Tom was obviously enjoying the feeling of getting his cock blown, even with a condom on, and I was loving making him feel good. As I was blowing his cock, I kept thinking, you're the seventh cock I've ever gotten a hold of, and in a minute, you're going to be the 6th cock that I've made blow a load in my mouth, and there is nothing you can do to stop yourself from coming. I slowed down to help him last longer, and kept looking up into his eyes. He was staring intently at his cock in my mouth, and didn't take his eyes off my mouth for even a second as I continued to slide my mouth up and down on his shaft. I was doing my best to take his cock in all the way to the base, so his cockhead could feel the tightness where my mouth joined my throat. I knew he wasn't going to be able to keep it together much longer. His hands were pushing down on my head and I could feel his knees bending and his hips pushing up to meet my mouth every time I sucked him in.
I must have slid my head up too far on his cock wanting to look in his eyes and he must have thought I was going to pull his cock out of my mouth because he suddenly clasped his hands hard on the back of my head and shoved my mouth down really hard onto his cock. There was no question that he was getting deep throated now, he was making sure of that as he held tightly onto my head and started force feeding me the entire length of his cock every time he shoved my head down. And then, holding tightly onto my head, with his cock shoved deeply into my mouth, he rolled over onto his side. With his cock locked deeply in my mouth, all the way back to my throat, I was forced to roll over with him. The side of my head was now laying flat on the bed and his cock was shoved into my mouth so far that his balls were touching my chin. He was lying on his side, but he could shove himself into my mouth at a slight downward angle. He had a tight hold of the hair on the back of my head and he was pulling my face tightly against his groin as he started to mouthfuck me very forcefully. And all this time, I had thought only Rick would fuck someone in the mouth this hard.
Tom's cock and balls were slamming into my face and his stomach was pressing against my nose as he continued to fuck my mouth harder and harder. He wasn't letting up, I was having a hard time breathing between thrusts, and his cock was starting to gag me. Suddenly I could feel his cock swell up just a bit in size and hardness and I knew he was going to cum. Within a few seconds his whole body arched as he jammed his cock as deeply as possible into my mouth and his entire body started jerking as his cum began exploding into the condom inside my mouth. I could feel his cock pulsing as he unloaded into my mouth, and I could feel each squirt he shot into the condom. When he was done, he rolled onto his back and looked like he would sleep for a week. I couldn't help but smile, I was thinking how much he had just enjoyed facefucking me, and how happy he was now. I very carefully slipped the condom off of his cock, folded it closed and took it with me to the washroom where I tied it shut, slipped it into my thong, and got another hot washcloth to go and wash off Tom's cock.
After I washed him, I slipped into the washroom and brushed my hair out and carefully re-applied my lipstick. I was totally relaxed now that Tom had shot off his load and was clearly very happy to have received my services. Just before slipping my dress back on, I counted the new bills in my pocketbook. As I stood beside the bed and slipped my jacket back on, I asked Tom if he felt better. "Oh, I can't even tell you how much better I feel. Please don't get mad if I don't get up and walk you to the door. And please don't forget to come and see me tomorrow night." I slipped out of the room.
I took the elevator back downstairs. I was going to do one more quick walk around and see if I could muster up any more stares before calling Rick to come down and get me. It was getting close to last call. Having guys stare at me just makes me so incredibly horny. I walked around a bit, definitely got a few more stares, and sat in one of the lounge areas to call Rick. I hadn't sat down for 5 seconds when a young guy, 20ish, walked towards the couch I was sitting on and plunked himself down beside me. The first words out of his mouth were, "Look, I know it's really late, and you are probably really expensive but is there any way you could help me out tonight?"
My coquettish response was, "Whatever do you mean?"
"Look, it's late, I don't want to waste your time, I am so incredibly horny, I have to get off, isn't there any way you could please come up to my room just for a little bit and help me out. I'll take anything you can do for me!"
I am such a softy! "OK, but I can only come up with you for just a few minutes. I have a client I have to meet in 15 minutes."
Five minutes later this young guy had me with him upstairs in his room. I have no idea what his name was or anything else about him. He was already laying on the bed, and I was sitting on the bed beside him and using both of my hands to jack off his cock as he fondled my tits through my dress. He was begging me to let him fuck me, or for me to give him a blowjob. "Just enjoy this baby, this will keep you happy for a little while at least." With that, I slipped the top of my dress down off of my tits and he started roughly squeezing them. I started jacking him off faster, and only about a minute later he shot a wad of cum that went straight up at least 3 or 4 feet. The instant he started cumming I rubbed him twice as hard and twice as fast. He was completely paralyzed as I kept stroking his cock. He was finally finished cumming and I let him go. I slipped the top of my dress back on and was putting my coat on when he slipped a bill into the top of my dress between my tits. What a sweetie, I hadn't asked for anything!
My work here was done. I headed back downstairs in the elevator. Walking down the corridor and headed for the bar where Tom had picked me up, I spotted Rick waiting on a couch. As I strolled along the hall, he got up and came towards me. He acted like he did not know me at all, asked if I had had a busy night, and what it would cost him to hire me for the rest of the night. I told him I had been with 2 clients earlier tonight, but didn't need to see anyone else tonight and so could squeeze him in. I told him that my prices were negotiable depending on what he wanted.
When we got to the room, Rick opened the door. We went inside and he turned on the lights and handed me a wad of cash. "Let's see how far this gets me," he said. I put the money in my pocket book with the other bills, and as we walked across the room towards the bed, Rick was already pulling my dress off. Once he had me out of my dress, he guided me onto the bed. "So, did anything happen with these other two clients, or did you just talk?" I told him how I had danced for one, and how he had titfucked me, and then how I had given him a blowjob. I told Rick about the way the first client had wanted me to put my hands behind my back and pretend to be tied up. I told him about the second guy who had received a quick handjob. Rick asked if there was any chance that he could get a blowjob tonight.
"Yes, baby, you are not going to have any problems getting a blowjob." With that, Rick excused himself to use the washroom and told me to make myself at home. A few minutes later, Rick came back and joined me. As we stood at the end of the bed, Rick turned me around so he was standing behind me and he reached around and started fondling my nipples and tits. His cock was hard, huge, and was pressed tightly against the crack of my ass. While he fondled my tits, I pulled the cum-filled condom out of my thong. I showed it to Rick, who said, "You must give a pretty amazing blowjob to get that much cum out of a single guy's cock."
"I give really amazing blowjobs, baby, you're about to find out just how amazing."
Rick laid me on the bed and then went and got a small suitcase that he brought back and put on the floor beside us. He pulled some items out of the case and asked if I would mind wearing them. He then proceeded to strap the padded leather cuffs first onto my wrists, and then onto my ankles. Next, he pulled out a longer strap that belted around my waist. And then he laid me back on the bed and laid his entire weight flat on top of me. He pulled the blanket up off the bed on each side of my waist, and clamped a restraint strap to each side of the restraint belt I was wearing. My hips were now tightly strapped down onto the bed. Rick had clearly been wrapping some restraint belts around the mattress while I had been out running around. Reaching up above my head, he pulled two more restraint straps out from under the blanket. He pulled each of my arms sideways above my head and clamped them down. With my arms stretched up above me, my tits looked huge!
With that, Rick got up off the bed and stepped back and took a good long look at me as he rubbed his cock. "Oh, baby, you are going to get so fucked tonight," he said. I was expecting him to pull some straps out at the foot of the bed and strap my feet down, but that wasn't quite what happened. Instead, he pulled out another strap from above my head, grabbed my left leg and pulled it way up into the air, and clamped my leg in place. He walked around the bed and clamped my other leg up into the air. I relaxed my legs and, as I did, my knees bent and I was lying flat on my back, with my feet up in the air and my knees pulled towards my head and pointing out sideways from my stomach. My ass was completely wide open for whatever Rick had planned.
Rick sat on top of me and slowly started to titfuck me. "Does that feel good baby?" he asked. "I'll bet you'd like this big cock shoved into that tight little mouth of yours!"
I played along with Rick's game and said, "Oh, baby, please don't try to stick that monster in my mouth!"
And with that, Rick pulled out another big surprise out of his little suitcase. It was a small box, but I could clearly see the word "large" stamped on the side of the box. I could also see a picture of a penis on the box, and at first, I thought it was a little dildo, but as he smeared a little oily lube on this new toy, I saw what it was. There was no way I was going to let him put that thing in my mouth. He tried shoving it between my lips and teeth, but I kept my mouth tightly closed. And then, while he kept pushing this huge cock-shaped gag against my mouth, he pinched my nose shut. At last, I had to take a breath, and the instant I gasped, he had the big cock gag half way between my teeth and because of the lube, I couldn't stop it. Plop, it was completely shoved into my mouth, and it was huge. I knew it was huge because it was even bigger than the head on Rick's cock, which painfully stretched my mouth every time I blew him.
Rick reached around behind my hair and tightly belted the cock gag into my mouth. I was trying to complain, but all that was coming out was mumbling. Rick looked at me and said, "You're not complaining are you, because I don't want to have to do this." And with that, he pulled something up in front of my face that I hadn't noticed while he was shoving the cock gag between my lips. There was a squeeze bulb attached to the gag. I had a huge inflatable cock gag strapped inside my mouth, and while it was already stretching my lips to the max, he hadn't even started to inflate it yet. And then Rick said, "This is what happens if you complain." He gave the bulb one full quick squeeze. I was amazed at the effect. One squeeze on this bulb that was outside of my mouth, and the cock gag jumped to life inside my mouth, and I felt it as it swelled out to more tightly fit against the inside of my mouth. Every bit of tissue in my mouth was now being stretched, and I could feel the massive cockhead squishing my tongue. "Are you going to complain anymore?" asked Rick. I was careful not to even mumble as I shook my head from side to side. "That's good, baby, because I'm going to keep this little bulb handy all night long in case you get out of hand."
With that, Rick reached over into his suitcase and pulled out a tube of KY lubricant. He squirted some onto his cock, and rubbed it up and down the entire length of his big shaft. Rubbing his cock in front of me he asked me to nod if I wanted to feel his cock inside me. I nodded and didn't make a sound. Rick got on his knees between my legs, pulled my thong panty over to the side, laid down on top of me, and slowly began to insert his huge cock into my ass. I was watching the clock beside the bed, and Rick proceeded to fuck me for 20 minutes straight while he kept telling me over and over, "Oh baby, you are so tight, oh baby, you are so incredibly super tight." He didn't slow down or take any breaks. With each passing minute, he fucked me harder and harder, and I started to experience the same feeling I had felt so often before. Please, Rick, please baby shoot your cum into me. I was moaning now in total pleasure. Whenever Rick seriously fucked me, I would drift off into this dreamworld of pleasure, and Rick was giving me a hard, serious fucking right now.
I could feel every inch of his long, thick cock sliding in and out of me and stretching me inside with every thrust. I was totally helpless to do anything but lay there and enjoy the long lasting, super deep fucking he was giving me. I was so turned on at this point that I began sucking and licking the huge cockhead in my mouth as Rick continued to fuck my ass. Rick could see the cock gag being sucked in and out of my mouth enough to know what I was doing, and he grabbed the squeezebulb and gave it another squeeze. As I felt the cock gag grow even bigger, I got even hornier and started trying to buck my hips up and down under Rick. He was so heavy that I could barely move, so I started rhythmically squeezing his cock with my ass. I desperately wanted to have Rick's cock in my ass and in my mouth at the same time. Rick was fucking my ass so hard now that I could feel my hips being pushed down into the mattress every time he hammered his cock into me. And as his cock swelled up inside me, I knew he was about to cum. In a few more seconds, I began to feel the incredible hot spurts of cum begin to fire out of the end of his huge cock and deep into my body in a powerful rhythm that went on and on and on as he continued firing away inside me, releasing at least 15 hard shots of semen deep inside my body. Whenever he flooded me full of his cum like this, I was overcome with this feeling of being totally owned by that huge, powerful cock of his.
Rick went to the washroom, and quickly returned. When he got back, he removed the huge inflatable cock gag from my mouth. And then, with me still strapped helplessly to the bed, he kneeled over top of me, with a knee on each side of my chest, and he slowly lowered his giant cock straight into my mouth as he leaned forward and held his weight on his arms above my head. During the first few months that I had lived with Rick, he had managed to pin me down on my back and had mouthfucked me like this. I had quickly learned never let his cock get near my mouth when he was on top of me, because he had fucked my mouth so hard sometimes that he had bruised my throat. Rick told me that he didn't do this to be mean, but that he got so horny when his cock was in my mouth that he just got more and more sexually excited and couldn't help pounding into me harder and harder.
While Rick had gotten a blowjob nearly every day we had lived together, it had probably been a year and a half sine I had let him fuck my mouth in this position. Evidently, in planning how to restrain me tonight, he had this in mind. I knew that my mouth was in for a super hard, super long, and possibly painful fucking. And Rick didn't fail to disappoint. He had already exploded once in my bum, so I knew he would be able to last an extra long time while he fucked my mouth, and he did. I knew exactly what I had to do in order to make it through this. I would have to carefully time my breathing so I could inhale every couple of times he pulled his cock back out of my throat. I closed my eyes and concentrated carefully on my breathing as I lay there helplessly and Rick fucked my mouth brutally for nearly half an hour. He finally sat up without pulling his rock hard cock out of my mouth. He told me to open my eyes and watch as he exploded into my mouth. With that, he leaned forward over my face again and started pumping hard, fast and deeply into my mouth and throat. Within a minute, I felt the eruption of sperm blast against the roof of my mouth, the next shot into my throat, the next shot around my tongue, a couple more shots into my throat, and, with his cock pulled halfway back out of my mouth, he fucked me hard and fast as he shot the last few blasts of cum between my lips. I sucked, and sucked, and sucked and swallowed every last drop.
Rick got out of bed, reached into his case of toys one last time and this time pulled out a red ball gag. I was afraid to say anything as he strapped the ball gag into my mouth. I had no idea what he was up to now. He reached back into his suitcase and pulled out a thick dildo with a thicker head. He greased the huge head of the dildo, and then pushed the huge head slowly and forcefully into my ass, leaving the rest of the dildo sticking out of me. With me still strapped to the bed in a position that left me wide open for anything, with the dildo hanging out of my ass, and with the ball gag in my mouth, Rick pulled his digital camera out of another suitcase.
Over the next 10 minutes, with the room lights on bright, Rick took at least 50 pictures of me from every angle. And then he told me he had just one more thing to do. He pulled out a brand new bottle of cream rinse. He said, "This is going to look just like cum on you in the pictures." With that, he started squirting, or dripping a lot of cream rinse in a lot of of strategic places all over my body. He squirted some on my thong panties. He dripped some along the length of my nylon covered legs, and onto one of my high heels. He shot some on my breasts and neck, and more on my stomach. He took about 20 more pictures to get the cum effect. And finally, he unstrapped the ball gag from my mouth and told me to close my eyes. He squirted a huge amount of the cream rinse on my face and hair. He took about 5 more pictures of my "cum covered" face.
The following week when I saw the pictures, I was amazed at how realistic the fake "cum" looked. Rick had printed the photos and put them in an album, and had evidently been showing it to his friends and telling them that he had hired me out for a huge bukkake party. With my tits, stomach, legs, feet, ass, face and hair literally covered in what looked like cum shots, Rick's fantasy had been fulfilled, and all of his buddies believed him about the bukkake party. Within a few weeks after our vacation, several of his friends phoned to ask me out, and I suspected that each one had seen Rick's new photo album starring me.
For the time being, we still had two more nights of fantasy vacation!