Let’s Make a Deal
Copyright 2011 Bad Penny Press
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All characters in this work are portrayed as consenting adults.
Any assumption otherwise is solely in the mind of the reader.
Let’s Make a Deal
Let's face it; being an older guy means that you don't have as many chances for a hook-up. It's not like I'm some homely guy who's ugly enough to make a freight train take a dirt road to avoid me. It's just that I'm older and guys my age are looking to hook up with attractive, young guys. A category I passed through 25 years ago.
Hey, I'm not really that old. I'm in my mid-fifties, but I guess that's considered damn near ancient to many otherwise potential fuck friends. I take care of myself and take pride in my appearance, so I'm not some overweight slob that only dreams he's some sex god. Again, it's just that I'm in that AARP-aged group that nobody's looking for in the Men Seeking Men section of your local personals site.
Now, that hasn't stopped me from looking at those sites. But even when I come across an ad for some guy with picture of a nice dick that doesn't live to far away, the most common response I get to my inquiry is, “thanks, but I prefer someone younger.”
Well, I'd like a young guy once in a while, too, but I'm finding that a lot of them that are open to sex with an older man are now advertising themselves as looking for a “sugar daddy” type of guy, with that little “wink, wink” and not so subtle hint that any time spent with these young gigolo wannabes was going to require ponying up a few bucks to partake of their pleasures. I guess it doesn't qualify as prostitution when it's done under the guise of “an arrangement.”
Still, I searched. And then, quite by accident, I did find one thing that had the potential to solve my problem. Well, as long as I got past one more little problem along the way.
A fairly local guy – meaning in my book that he was within an hour's drive – was advertising something that I had always wondered about but had never really followed up on. He was selling a life-sized, “gently used” male silicone sex doll, purported to be “as good as, or better than, the real thing.”
Included in the ad were a couple photos of the sex doll, in various positions to show off the anal opening and rigid dick that looked to be about the advertised 6 inches. Also included was a picture of the doll's face that kind of looked like a wax-house likeness of Heath Ledger with permanently parted lips. (Then again, maybe I just assumed it to look like the actor with the movie “Brokeback Mountain” in the back of my mind.)
Well, it did look reasonably lifelike in the photos, and the dick itself was kind of molded perfection that any decent cock-loving guy would happily play with. I was, to say the least, interested. Even when I took into consideration the little problem that I mentioned earlier: the price.
Dropping $1500 on a hunk of silicone, no matter how fuckable it might be, was a serious chunk of change to be forking over. So much so that it kind of made tossing out a few bucks for one of those arrangement-seeking youngsters almost attractive. But, this little rubbery dude for sale wouldn't be passing on any diseases or drinking all my beer when I was gone, so the more I thought about it the more I became interested.
Finally, almost impulsively, I typed up an e-mail about my interest and sent it off to the seller. Just as he hadn't posted a phone number in his ad, I didn't yet give mine out, also preferring the anonymity, at least for now.
But it wasn't even 5 minutes later when I got his response. He included a phone n umber and his name. So, still seizing the moment, I called him up. After a couple rings it picked up on the other end. “Hello?” came a voice.
“Greg?” I asked, trying not to sound as nervous as I was feeling.
“This is Greg,” answered the voice. “You the guy callin' about the ad?”
“Yeah, that's me,” I said. “What more can you tell me about the... doll?”
“Well,” he said with a sigh, “I could tell you lots about it, but I've done that with a few guys already who were pretty much just flakes.”
“I can hear the frustration in your voice,” I said with a slight chuckle.
“Yeah,” he replied with the same small laugh. “I kinda think that if someone is truly interested they can come down here to look at it in person. Then if they're not interested after that, at least they invested something, even if it was only their time and gas money.”
“Well, if you give me a time and location, I'd like to check it out.”
“Any time's good,” he replied as he told me where he lived, only about 20 minutes away. “I live alone and I'm here for the next two days.”
“I can be there in a half-hour, if you'd like,” I said.
“Works for me,” replied Greg as we hung up.
Staying true to my word I found Greg's place and was knocking on the door 30 minutes after our conversation. When he answered the door he looked me over a few times and said, “You look pretty damn normal.”
“What, for a guy that's interested in buying a gently used sex toy?” I asked, finding myself laughing at the absurdity of our situation. “You look pretty normal, yourself.”
“You mean for a guy that has sex with a fake dude?” he asked with a snort as he gestured me into his home. I entered, noting that the place was pretty clean and well kept.
“I'm assuming you're not married,” I said, “but you keep a real nice place.”
“Got a cleaning lady that comes in here once a week,” replied Greg. “I gotta hang Woody in a locked closet then.”
“Woody?” I asked, trying not to laugh at the notion that a guy would name a sex doll.
Greg walked over to a stuffed chair where a white sheet covered everything but a pair of bare feet sticking out at the bottom. I noticed the sheet also had a little 'tent' in the fabric. He reached out and took hold of the sheet right where the tent was, pulling the sheet away and revealing the advertised sex doll in all its naked glory.
“I named him Woody 'cuz he's always got a woody,” said Greg, wadding up the sheet. “Lucky bastard.”
I looked down at the bald silicone version of masculinity, looking surprisingly real and, to be honest, very enticing.
“Handsome thing, isn't he?” Greg asked.
“Yeah... yeah, he is,” I replied, noting in particular that the silicone flesh was smooth and void of any attempt at fake pubic hair, making the doll look all the more inviting. “Why are you getting rid of him?”
“You know, I really don't want to,” he replied. “I mean, I really enjoy playing with him, but I'm on the road so much and I can't take him with me when I'm staying in some hotel for my company, so it seems like he's kinda going to waste here.”
“Yeah, I can't imagine that you could sneak him into a hotel room very easily,” I said, staring at the rigid silicone dick jutting out invitingly from Woody' smooth body.
“Would you believe I dropped five thou on him almost 3 years ago?” asked Greg, sounding a little surprised at himself. “But, he's been worth it.”
'He', not 'It'. Funny.
“You might as well feel him out,” Greg said. “The mouth and butt openings aren't stretched out, and the dick is nice and firm, like when we were teenagers.”
I did as Greg suggested, probing the mouth with my fingers and finding that the teeth were flexible and bent out of the way as I pushed inward.
“It even develops a vacuum while you're using the mouth,” Greg said like a true salesman.
I reached down and took a hold of the stiff 6 ½ inch dick and felt my own cock twitch in my pants. Still holing onto the rubbery dong I reached down with my other hand and slipped my fingers under the fake scrotum and between the gel thighs. I found myself getting rather excited as I probed around and finally found the anal orifice.
“Still tight,” Greg said. “My dick's not big enough to stretch it out.”
“I'm sure your dick's just fine,” I replied, off-handedly complimenting Greg on his dick before I realized it. If he took it as an odd response, he didn't let on. “You're right. He feels pretty tight.”
Crap. Now I was calling it a “He”.
“I keep him real clean,” said Greg. “Kinda douche him out with soapy water and then some alcohol, hang him up to dry from the neck bolt. I even bathe him in a warm tub about once a week.”
“Well taken care of,” I said. “Still, fifteen hundred bucks is a lot...”
“How about twelve-fifty? It's a quarter of what I paid for him,” said Greg without sounding defensive. “Once you lube him up and stick your dick in him, you'll find he's worth it.”
“Probably, but I wouldn't find out until we're home,” I replied. Then jokingly I added, “I don't know if we're compatible yet.”
Greg laughed and then fell silent as he seemed to suddenly get lost in thought.
“I guess you could find out,” he said.
“Excuse me?”
“If it'll make the sale, you can take it for a test drive, I guess,” Greg said, confirming what I thought I had heard.
“Fuck your buddy right here and now?” I asked, surprised.
“It's not like we've got anything to be embarrassed about,” Greg said before clearing his throat. “I mean, you know I've played with it and that's why you're buying it, you know?”
“Uh... right here?” I asked.
“You don't have to go at it if you don't want to,” replied Greg. “But if it'll make the sale...”
Now I was in a bit of a quandary. I found myself really wanting to buy the damned thing, but dropping a whopping twelve hundred bucks on a used sex doll meant that I was stuck with it whether I liked fucking the thing or not. That said, was Greg joking about taking a “test drive”, or was he really going to let me stick my dick in it while under his watchful eye to make the sale? The thought of being watched was both a little disconcerting and kind of exciting.
“I'll get the lube,” Greg said without waiting for an answer, a hint of excitement in his voice. “You're, uh, gonna need the stuff, anyways. It comes as part of the deal.”
When Greg returned he almost looked disappointed that I hadn't prepared myself for a test run. Now feeling obligated, I sat down on the couch opposite Woody and under his and Greg's watchful eyes I took off my shoes and then undid my pants, sliding them and my briefs off in one move. I stood up and pulled my t-shirt over my head, my dick thickening a little as Greg seemed to actually admire my body.
“Well, where does Woody like it best?” I asked.
“I, uh, just lay him over the arm of the couch,” he said. “It's kinda the perfect height for a good penetration. Your legs are about as long as mine, so it would probably work real good for you.”
I took it upon myself to go over to Woody and pick him up.
“Not by the hands,” Greg cautioned. “It can damage the wrists. Pick him up from under the arms like you would a real person.”
“What's Woody weigh?” I asked
“About 75 pounds,” replied Greg.
I did as Greg told me, reaching down to slip my arms under Woody's armpits and lifted him up and out of the chair to his 5' 9” height. I was surprised at how real his “skin” felt in my arms, and Woody's permanently stiff dick rubbed against mine as I held him up, just adding further to the excitement.
I easily carried Woody the few steps to the well padded couch arm as the rubbery dildo sipped between my thighs , exciting me to the future possibilities there. But for now, it was going to be my dick in Woody's silicone butt.
I swung Woody gently around and eased him down onto the couch arm face down where his exposed anal opening stared at me above the firm rubber penis pointing at the floor.
“Wow,” sighed Greg.
I looked up at Greg and then followed his gaze down to my fully erect dick. In all of the moving of the male sex doll and admiring how real and waiting it looked, I had grown fully hard.
“That's pretty huge,” Greg said. “Woody's never had anything that large.”
I was flattered and excited. Greg handed me over the bottle of water-based lube and I flipped open the top and began to pour a little onto Woody's waiting opening.
“You need to work a little of the lube in with your fingers,” Greg said as he watched me prime his friend.
I did as Greg said, and found myself getting even more turned on as I slid my fingers in and out of the pliant material, readying Woody for my back door attack.
“That should do it,” I said, breathing heavy in anticipation.
“You should smear some lube on your dick, too,” Greg instructed. “Especially you because you're pretty thick.”
I poured a little of the lube on my prick and rubbed it all around until my erection was glistening.
“Now?” I asked Greg.
“Just take it easy on him,” Greg replied. “He's not used to you.”
I wanted to burst out laughing, but instead I handed the bottle of lube back to Greg and steeled myself for what I was about to do; fuck a fake man in his fake ass in front of his owner.
I put the head of my dick against the opening and gave it a gentle push. The silicone resisted me at first and then finally stretched and gave way. Before I new it, my dick was enveloped inside one of the firmest, most gripping orifices I'd ever stuck my dick into.
“Feels nice, doesn't it?” Greg said knowingly. “If it was tight on me, I can only imagine how it feels to you.”
I had to suck in a deep breath as I had not been prepared for how good the damn thing would actually feel around my prick. Along with all of the other crazy things happening around me I was damn near cumming already. I took a chance and started to slowly withdraw my cock until it was just on the verge of falling out, and then shoved it just as slowly back in.
“Jeez, that does feel nice!” I sighed.
“Woody's got a great ass,” Greg said. “His mouth is good but his ass is incredible. Go ahead and fuck him good.”
I braced my knees a little at the edge of the couch just inside of Woody's pliant thighs and started to build up a rhythm until I was freely sliding in and out of the doll's ass hole. The lube was working perfectly and the canal had created a vacuum that sucked on my dick enough to make my head swim.
“Man, you got a great cock,” Greg said as he watched my dick working in and out of the silicone toy. “You should have been a porn star.”
I didn't say anything but noticed that Greg was absentmindedly rubbing the growing bulge in his crotch through his pants. Watching Greg rubbing at his bulge while he was so intensely focused on the action of my prick sliding in and out of Woody's barely forgiving silicone ass just added to the excitement. I figured I might as well really go for the gusto.
“You know,” I ventured, “you're probably gonna have to take that thing out of your pants before you hurt yourself.”
“Huh?” responded Greg, surprised. “You mean that?
“There's three of us and only two of us are having sex,” I said. “It's only fair that you join in.”
Still trying not to take his eyes off my pumping prick, Greg stripped down until he was only in his socks. Then he got back onto his knees and stroked his rapidly hardening dick in pace with my thrusts.
Greg's body wasn't too bad looking. A little soft around the middle, a trace of man boobs, but pretty hairy on his chest and stomach. Yet his pubic hair was trimmed nearly to the point of not being visible. That trimmed hair revealed a dick just a little smaller than Woody's fake prick once it was fully erect.
Watching Greg stroke his very attractive hard-on was getting me more excited by the minute and I would blow my wad into Woody in just a few more strokes. But I decided that I wanted to make this one last and stopped pumping into the silicone ass.
“You know, it, uh, would be a shame to jack off when you have a willing mouth available to you.”
Greg looked down at the head of our silicone friend excitedly. “I'd sure like to, But I wasn't sure if you wanted me to take him from this end since I promised you a clean doll.”
“I, uh, wasn't talking about the doll,” I said with a little trepidation.
“You mean...?” he asked excitedly.
The look on Greg's face was priceless. He appeared as though he might have been wishing in the back of his mind for such an opportunity, but perhaps wasn't sure how to approach it.
“Come on,” I said encouragingly. “Bring that over here and stick it in my mouth while I fuck your friend's plastic butt.”
Greg shuffled on his knees towards me, trying not to disturb the couch cushions as he carefully straddled the body of our inanimate fuck friend. He raised himself to his feet as he braced himself against the wall with an outstretched arm to keep his balance until his erection was bobbing just inches from my face.
Seeing Greg's dick pointing right at mouth, I had a better view of just how attractive it really was. It was crowned with a rather conical head that rested upon a thickly veined and slightly upturned shaft. Greg's scrotum was tighter than the sex doll's, almost disappearing into the crease of his thighs.
“Let me suck you,” I said. “Feed me.”
I opened my mouth as Greg leaned forward and cautiously slid his dick about halfway into my mouth. Apparently he was unsure about how much dick to feed me. I started to work my dick in and out of Woody's greased orifice again, surprised at how well the lube was lasting. As I built my rhythm up again, I matched it with strokes of my mouth on Greg's sweet prick.
“Christ, that's nice,” Greg sighed.
Within a few moments I relaxed my mouth enough that I was taking Greg's entire length until I was mashing my nose into the soft pudge above his cock and his tightly bound testicles were just on the verge of following his dick into my mouth.
“Holy shit, man!” Greg growled out, surprise forming his words. “God, that's wonderful!”
I couldn't agree more. I was pounding my cock hard into Woody's slippery silicone ass while sucking Greg's very real dick into my mouth and savoring the sensation the head and veins were transferring to my tongue and the roof of my mouth. It only hastened the fire growing in my belly. I started to shake all over.
“I'm gonna cum, man,” Greg said. “I'm gonna cum in your mouth if you don't watch it!”
Shifting my weight to my right arm, I took my left and reached up to grab the back of Greg's meaty thigh and held fast to him, telling him in no uncertain terms that I had every intent to have him shoot his load into my mouth.
“Fuck!” howled Greg. “Here it comes!!”
Working my sucking and fucking in unison I was just as ready to cum as Greg when his dick started to twitch in my mouth and I could feel the first rush of his seed pump through the shaft of his cock and right into the back of my throat.
“Oh, God!” yelled Greg again as another musky, salty burst erupted from his sweet dick, coating my tongue with its thick cream.
At that very moment my own dick loosed with a massive load into my silicone lover and quickly filled the tight tunnel. I was surprised at how much cum I was ejaculating, so much that my continued thrusting was causing my load to squirt past my pumping prick and out onto my thighs.
Greg was quickly fading along with his ebbing ejaculations, weakening even as I increased the suction of my mouth on his tool to try to hold him in place so I could continue to enjoy a moment that happened all too few times.
Finally, Greg pulled his drained dick from my mouth and staggered back, landing on his butt on the opposite couch cushion and looking just as satisfied as I was sure his dick was. Likewise, I withdrew from the intense grip that was Woody's anal orifice and fell to my knees where I was eye level with the slightly stretched silicone sex toy and watching my cum run out of the hole and down the rigid dildo suspended from between the squishy thighs.
“Well?” Greg asked in a strained voice.
“I'll take it,” I replied. “On one condition.”
“What's that?” Greg croaked out.
“Woody here was really good and all. I mean, it felt really nice,” I said. “But, I think the best part was having your dick in my mouth, too. If you're game, there's no reason why we can't get together again.”
“A living, breathing person sure beats fucking a hunk of silicone any day,” agreed Greg. “Finding one when you're our age is another story.”
“Well, I think we found a couple guys our age willing to fool around,” I said. “And with Woody here, just like today I think we might even have some great threesomes.”
“Then I'll make you a deal,” Greg said. “A thousand bucks and you spending the night tonight and teaching me how to handle that monster dick of yours in my ass. That, and my work schedule so you know when I'm available to get together with you again.”
“Sold,” I said.
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