A variation of a real experience with a male escort
More than I paid for
I'm an older man in my early 50's and it just seems the older I get the hornier and kinkier I become. Married with a couple kids I've played safe off and on through the years around my sexual but unadventurous wife. This has include some play with professionals and amatuers alike, including some couples and a few single guys. That's where this story begins.
I've been with a few guys, mostly give oral and just a couple willing to fuck me. Yes, I'm one of the thousands of mostly bottom guys out there. It's a preference for a few reasons. One, I'm not well endowed and secondly, I usually get a good amount of sex as the agressor, top or orchestrator at home. It's things I can't get at home that I usually look for. I've always been open to being versatile with a guy or couple but my lack of length usually is the deal breaker. Similarly, I've had little in the realm of hung guys meet me. I'm not a size queen but I'd always wanted to try someone hung more than 4-6 inches. I'd even gone to professional women with strap-ons but hadn't found one "sane" who had a larger strap-on, unless she was a dominatrix which tended to be a bit high rent for just getting a good hard pounding.
So this led me to looking through some on-line ads one night. Male escorts ads. Someone who would care (or would pretend not to card) that I wasn't 18-25 or hung like a small pony. I responded to a few guys who noted they were larger than average with noting race (didn't matter). Rates seemed pretty comparable and some were more open about ensure I wasn't just going to get a back rub for my money while keeping the conversation light (as in to avoid law enforcement). So I picked one guy who seemed to be straight forward and understood that I just wanted to get a guy hard orally, have him patiently work himself into me and then use me like a blow-up fuck doll. He was clear that when I left our encounter that I knew I'd been used. He told me he was agreable to that and told me more stats about him (close to my 6 foot height but about 30 lbs heavier than my 200 lbs) and that he was dark black and his name was Darryl. I said I don't care about race, just cleanliness and able to fulfill my desires. We set a time to meet the next day at 1 pm.
I prepared that day with a good Fleet enema, shower and a couple beers. I purposefully left home earlier that morning to avoid masturbating and losing my horniness before meeting. I showed up promptly at 1 pm at his apartment and after knocking a tall, black man answered the door. I thought, shit, I've got the wrong place. I stammered out that I was looking for Darryl and he said hold on. I could see another guy sitting in a chair and from the sound of the television knew they were watching some college football game.
What seemed like an eternity later Darryl appeared and came outside and shut the door. He explained that his roommate skipped work and they were just hanging out. He said they'd probably leave in a bit but understood if I didn't want to stay around and apologized again. I'd been wanting this awhile so said I'm open to making this work somehow. He thought for a moment and said follow me. We walked in and introduced me as Steve, someone who worked with him before and we're going to his room to talk about a possible job. The guys barely gave me a second look.
We walked into his room and I was impressed. It was a well lit room, clean and generally looked like any guys room in his 30's, even with a couple Playboy's on the nightstand. He closed the door and apologized again. After a few minutes of small talk and getting us both a beer he asked me if I'd like to suck his black cock. I smiled. I said, sure - doesn't matter the color, just as long as I can get it nice and hard to fuck me. At this point I completely forgot about his roommate and his friend.
Darryl puts down his beer and undoes his belt and pants and just let's them fall to his ankles and tells me to come over and help myself. He's wearing tight boxer briefs and you can see the outline of a small snake starting to stir. I get in front of him and yank down the front of his briefs and take the head of his cock in my mouth. I didn't want to hesitate and have him get fully hard, I wanted that to happen as I sucked him. I gently cupped his medium sized balls and bobbed slightly on his hardening cock.
He's starting to get hard in a hurry. I'm hoping I'm doing a good job on him and try to take as much of him as I can. He's hard and certainly longer than any guy I've seen in person but not very thick. I'm good with this as my oral skills need work and I really don't need a coke can in my mouth. Darryl starts moaning a little and starts to tell me I'm his good little cock sucker when his bedroom door swings open. It's his roommate already mid-sentence into an "oh, there you are, hey we are going to..." when he sees me with Darryl's cock firmly in my mouth.
After a few ackward seconds his roommate makes his own apologies and walks back out the door. Darryl pulls his cock from me and says wait here and manages to exit the room, struggling to put his pants on. Now I'm anxious. This could get weird or more weird soon.
After a few minutes Darryl comes back in and says everything is cool. He hadn't told Jason (his roommate) that he's bi and likes to make some money on the side fucking guys. He says they were just about to go out for lunch and broke in to see if they wanted to pick up something for him. Now they would like to watch.
Watch! Sure, I guess was my response. Why not. It seemed surreal but it seemed like a fun idea at the time. Darryl said cool, opened his nightstand and pulled out lube and a condom and said follow me and walked into the living room. He introduced me to Jason and his friend Mike then said why don't you get me hard again. This time I did all the work to get his pants and briefs down and sucked him again. He was already fairly hard when I started so he just let me suck for a few minutes. I could taste some fluids as he seemed to be on a fast track to fucking me.
He told me to strip now, so I stopped sucking and just took off my clothes. Only when I got them off did I remember the two other guys and looked at them. I got anxious pretty quickly as I couldn't tell from their looks what they thought. Then Mike asked, "You going to let him fuck you?" Yes was all I could say.
Darryl told me to just bend over first, so I'm stand and bending over like I'm doing toe touches and feel his rough hand slathering some lotion in and around my ass the firmly plunged a finger in. I gasped a bit. He wiggled it around and included some more lotion and finger fucked me at a slow speed with first that single finger, then a second, then a third. He wasn't in a hurry but he didn't waste any time when he thought I was ready for more.
He pulled away and from the sounds figured he was putting on the condom and lubbing that up. He laid his longish cock above my butt crack and pressed in, like a hot dog into a bun, and rubbed it up and down. He was trying to get harder. After a few more strokes he told me to look up at the guys and spread my legs a bit. I looked up and gave them both a glance. Jason had this curious look on his face while Mike had a blank face but was rubbing his crotch. At that time I felt Darryl's fingers again for a few quick deep entries then he placed the head of his cock at my backdoor, grabbed my hips and pushed slowly.
Although it had been awhile I remembered to push back a bit and try to open up. I felt the familiar initial pain then I felt something I hadn't ever experience before, he plunged in just about balls deep. I don't know that I can describe the look or pain I felt but it was wonderful for a moment then very painful, then relief as the pain subsided from sharp to just about what I'd expect.
He didn't move for a few moments and asked if I was alright. I asked him to just be still a moment or two then told him I was okay. With that he pushed in a bit more then pulled about half way out. That took my breath away. He slowly worked in and tried to got a bit further. I didn't think he had much more to go and was right. A few more times and I could feel his balls and pelvis fully bouncing on my ass.
As he stayed there I knew I was still going through an adjustment with his cock firmly in my ass. Although not thick, I definitely knew it's presence and also that I felt fuller and slutier than I ever had before. He started to slowly pull out and back in, a bit further out each time. I think I let out a few "Oh gawd" in there. He pulled all the way out, lubed a bit more and slowly let my ass engulf his member. He then asked me to tell his friends what I really wanted today. I looked up at them and said "to be fucked like a slut." He asked "and what else" where I replyed "hard, for your amusement." I think a blush came over me.
He quickly pulled out of me and told me to get on all fours. I quickly complied and without any more thoughts about my inexperienced ass he proceeded to plunged deep inside me and fucked me across to the carpeted floor. It was great. It still hurt a bit but he we definitely touching the right spot. I was starting to get pretty vocal and so we he. Between my grunts I found we slid across the carpet until I was practically in Mike lap. I had my head down and it bumped into his chair. I looked up and saw a smaller but thicker cock pointing right at me from underneath his shorts. He had removed his pants at some point and his hard cock was pointed right at me. And he was stoking it.
Mike asked me how much to suck him? I grunted out I had no more money (hadn't paid Darryl yet, put I did before I left) but I'd do anything for his cock and cum. I blurted out I'll let you cum on my face and I'll leave the apartment with you cum there. His only response was to feed me his cock. I tried to concentrate on sucking him but Darryl was in the middle of giving me a new asshole. With no where else to slide off to he was giving me the business and I could feel sweat dripping down off him onto my back.
After another 10-15 min Darryl pulled out for a second. I welcomed the rest so I could concentrate on Mike's cock. I felt some more lube and felt Darryl pushing in again. He was having trouble as I seemed to have clenched a bit so I just beared down and threw myself back onto him. About 2 seconds later I realized it wasn't Darryl, it was Jason and fuck he was big. I hadn't seen his cock at all but it was thicker and longer. I screamed out in pain.
Jason said, "take all of my fucking cock, bitch" and started hammering my ass. I couldn't do anything more for Mike. I was being impaled. I just put my head down on the chair with Mike's cock laying on the side of my face while the assault continued. Mike moved away and Jason forced me to hang and hug the chair for balance and he reamed me. I was in heaven. I don't know how long it was but at some point Jason pulled me back off the chair and and flip over onto my back. He quickly pulled me to him by my legs and rammed his cock fully in, feeling different but just as deep as before. He then pushed my legs back towards my shoulders and said, "You wanted to get fucked, now you've got your chance" and proceeded to fuck me harder and deeper than before.
Shortly after that I lost my nut. It didn't cum out in real spurts more as one big spurt and a bunch of twitches. I was still be deeply fucked. About 1 minute later I noticed Mike kneeling next to me jerking his cock. I tried to reach for it with my mouth when he just came on my face. The first bolt grazing my check, the second on my nose and the rest across my mouth. No sooner than he moved away Darryl did about the same thing from the other side. However, he aimed right between my eyes. A couple minutes later Jason, who had slowed down a bit, started to grind me real hard then pulled out this baseball bat of a cock. It was heavy and only partially covered by the condom. He yanked off the condom and crawled up and lifted his heavy member to my face and started playing with the tip and told me to open but do not swallow. He breathed deeply and let out a yelp as rope after rope of cum shot in and around my mouth. Soon the cum was running out of my mouth and down my chin. When he was done he told me to spit the rest out of my mouth and wear his cum like a good whore. After I did that he pushed out the remaining cum out of his limping member and stood up and said, "that was fun, where are we going to eat?"
I quickly thanked them and they didn't really say anything other than to start getting dressed and/or cleaning themselves up first. I dressed quickly, cum still dripping off my face onto my body, clothes and floor. Left my donation and slipped out the front door. I tried to race to the car but my ass was too sore for any quicker pace. It was at that moment that I realized I got more than I paid for - but exactly what I wanted.