Gamble for One minute? Ch. 03

Story Info
Tricked into confinement.
3.7k words
4.38
23.2k
8

Part 3 of the 4 part series

Updated 06/07/2023
Created 03/17/2015
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Make sure to read part I and part II, you will miss the background without it.

*****

It was Monday, I was picking up supplies at the lumberyard for today's project. While loading the 2x4's, I noticed this guy glancing at me, twice actually. He didn't look familiar to me, but there are a lot of people that know me and I am not too good with names or faces. I secured the load and headed into the office to sign for the stuff and get my receipt.

He was waiting for me outside and said, just before I hopped in my truck, "Mark told me all about your visit to his girlfriend last week." He was smiling ear to ear. He was one of those little guys that naturally tried to make up what they were short by hassling others.

"I have no idea what you are talking about." "I don't even know this Mark dude you are referring to." I told the little guy while I slammed the door shut.

"Oh, he said that you couldn't even last a minute standing before his girlfriend!"

WTF I thought to myself, this dude has no idea how I was tricked into that mess, so I replied angrily: "I wonder how you would do if her mom was jerking you off while she dropped her tights!"

I started the truck. Put it in gear, and noticed this little guy just turning white out of amazement. His mouth dropped open. If it wouldn't have been attached, his jaw would have hit the pavement! Crap, he didn't know, and I just gave that detail away. Nice Monday morning!! I cursed to myself and drove off, a little too fast.

During the drive to the jobsite, I replayed the scenarios one after another. Maybe I just had to accept that these folks were super un-conventional, at least in their view of sexuality. To them this may be just a big joke, I mused to myself, quite annoyed.

"HOOOONNNKK!" it sounded from ahead of me. Some truck just honked at me and I saw a glimpse of the dude waving and just laughing out of control. No idea who it was, but since there was a bunch of plywood in back, I guess another one of Mark's buddies.

Great, I thought to myself. Now I have a reputation that I will never live down. But then, I could always counter any of their comments with: "How many times did Laura dance for you?" That would shut them up for sure. I pulled up to the job. It was time to put these thoughts aside and get to work.

As the week went on, I ran into countless folks that would make sneering comments. Some funny, some not funny at all. But, I thought to myself, they either have too little going on themselves, or are simply jealous. I made sure not to give any of them much for extra food for thought though.

It was time to start the deck project. With supplies and tools in back, I headed over to Pete and Karen's place. It was a little early though, and I remembered Karen asking not to start exceedingly early. She liked her night's rest to last as long as possible.

Off course, my mind was full of thoughts as I approached the place. Maybe it would be a good idea to empty out, just since I had the time, and to make sure I didn't get my horny self in trouble again? I found a private parking spot and started rubbing myself. Oh, with thoughts of skintight tights, it didn't take long to get ready.

Knock, knock. My heart skipped a beat, two actually as I jumped in my seat and got yanked back to reality. I looked over. There was the face of Laura, the face I was just fantasizing about, sweet enough to give an alligator cavities, looking into my window. She had her hands up next to her shoulders and asked "What are you doing?" as I tried to make myself presentable as soon as possible.

As I tucked everything away, I rolled down the window. "What are you doing?" she asked again. By now my face was beet red.

I stammered something that was supposed to sound like a question to her, where did she come from?

She ignored the question and said: "My parents are looking forward to you starting today. I just ran out for some fresh baguettes and saw your truck here. I was afraid that you were starting a job somewhere else, so I stopped." She smiled again, as she said: "Little did I know that you were indeed starting a job here" and giggled. "Let's go, I am sure that by now the coffee is ready."

As we walked in, Laura told Karen and Pete: "Guess who I found on my way back from the store?" It was a question that needed no answer, and everything would have been fine if she would have left it at that. But I so had underestimated their non-conservative attitude.

She continued and said: "And guess what I found him doing in the back of the parking area?" as she smiled with a telling look on her face.

Karen picked right up on that one. "Oh, I know right what was happening, and I bet I can even guess just who he was thinking about in the middle of that." she said. My face was beet red, that alone gave everything away. Nice start of the project I thought to myself.

"Coffee?" Karen asked as she poured me a cup. No, I really didn't want coffee, I really wanted out of there and to just go to work, but that did not seem to be a possibility, not right now. So, I accepted the coffee and as soon as I reasonably could get away from these crazy people, I did.

Outside, at last, I thought to myself. And with all that pent up energy, I got to work with a vengeance.

At the end of the day, I looked over what I had accomplished. I was very happy with the progress I had made. Part of the frame was up and you could start to imagine what it would look like when it was done.

It had been a hot day and as usual, I had taken my shirt off. My shoulders were slightly burnt by the sun and I was in desperate need of a shower.

Karen noticed I had cleaned up the tools and was getting ready to call it a day. She came out and was full of smiles. "Looks great!" she said. "Take a quick dip in the pool to freshen up and have a beer with us." She sounded real.

And I had already been eyeing that pool, not only because earlier that afternoon Laura decided to swim a few laps and work on her tan. No, words could not describe how good she looked with that bright yellow bikini. But it was work time and there was just enough distance between the deck and the pool that I could stay focused, more or less.

After a few lazy laps, I was starting to get cold. The pool was unheated and it was still early in the season. I hopped out and tried to shake some of the water off. "Towel?" Laura asked, holding out a neatly folded towel.

I accepted happily and dried myself off. As I stepped in the door, Karen said: "you can just leave your wet things by the door." Crap I thought, is this all a trick to get me naked again? "Oh, don't be so shy, we have all seen you naked already, and you must be getting cold." Karen giggled. That was true, and my wet shorts were definitely cold now the sun had gone behind the trees.

With a sigh, I took my wet shorts off.

"What is the deep breath for?" Karen asked smilingly. It was obvious she had something on her mind. "We already know you are a grower, so you don't have to be embarrassed now you are cold." she giggled.

Oh, I could feel the blood rise to my face. I quickly glanced down and no joke, I didn't think it could get that small. I sort of draped my towel around me as Pete pointed at the open beer that was sitting on the table.

"You made a lot of progress." He said. "It looks great!" and we had a brief conversation about next steps and how the new and old would blend even though there would be a color difference.

Karen walked towards us at the table. I could have imagined it, but I was sure she had something on her mind and she was just waiting to bring it up. "Oh, My!" she exclaimed. "You are all burnt by the sun!"

It was true, it wasn't too bad when I was still outside, but now it really started to show. "Oh, I will be allright." I said.

"No, this is not good, Laura go get that suntan lotion you took downstairs yesterday." she asked Lauren.

I didn't trust what was happening, and asked: "That better not be that pink lotion you used on me the last time" I said.

She grinned, Pete grinned. "Oh, you didn't like that?" she asked mockingly.

"No, not at all, the heat seemed to get worse for a long time after, before it faded." I said. "What was that stuff?"

"It is called: Linger, Zinger" she said. "And it is supposed to make sure you don't forget what you just got." She giggled. "And I guess, it hit the mark."

Laura came back with the suntan stuff. It was indeed ordinary suntan lotion, with aloe vera, it said on the label. Still I was weary about this situation. "So, why do you all of a sudden want to ease my dis-comfort if last time you wanted to make sure I left hyper un-comfortable?" I asked. I didn't trust this situation at all. She was up to something. I asked: "Are you just trying to get your hands on me?"

I remembered her look at me when she made me count. It was very obvious she liked looking at me then. And now, I was wearing even less than I was then.

I looked up at her, rubbing the suntan stuff on my shoulders, expecting a reply. She just smiled.

I was super curious as to her thoughts. "OK, out with it!" I said. "What is on your mind?" By now all three of us, Pete, Laura and I were looking at her.

"Oh, I was just thinking about the burn on your shoulders." She said.

"Nice side step." I said. "We all know that wasn't what was on your mind."

"Yes mom, tell us, you can't be the only one having fun here." Laura said.

"Well, if you must know, I was thinking of that wrestling match we saw in Vegas, where the couple was shiny with oil."

"Ooohh," Pete and Laura went. I wasn't exactly sure what they were talking about but assumed they went to an adult show and oil was part of the scheme.

"Yeah" Laura said, "She got him good!"

Now it was my turn to be curious, and asked: "Let me guess, they were both naked?" Karen nodded. "And the girl suckered an orgasm out of the guy?" I asked.

"No, not exactly" Karen answered.

"So what happened?" I asked, while I looked at her face, trying to unearth the thought on her mind.

Pete seemed to know already where this was headed. "You can't possibly be thinking these thoughts, Karen." He said. "He is almost twice your size."

Crap, I thought. Somehow her massaging the suntan lotion on my shoulders made her think of putting her hands all over me in a wrestling match! While Karen wiped her hands and the remaining lotion on a towel, I looked at her and thought to myself, yeah a wrestling match with her would be over in three seconds flat. I am a strong guy and while she may be in great shape, I must be almost double her weight.

"True." Karen said. "But then, if I would enlist some help..." as she looked over at Laura.

Laura didn't need any prodding: "Yes!" she almost yelled. She was obviously excited, her smile was all over.

WTF? These chicks want to wrestle me? "Pete, you can't possibly be OK with this?" I unbelievingly asked Pete.

"Oh, you have no idea." he said. "This is some kind of foreplay, and later, I am going to take over where you leave off." The look on his face wiped away any doubt I could have had. These people really, really, really have some unorthodox beliefs as to sexuality.

Still, I was way leery about where this was going to go. After the two last events -while fun and the core of many fantasies- I felt way taken by Karen and I wasn't going to agree just like that. "OK, so what happened to the guy in vegas?" I asked.

"Oh, she tied him up and took his orgasms." Karen replied.

"Was that orchestrated and fake?" I asked.

"No, the regular guy somehow didn't show up, so they found some guy in the audience to take his place." "He just had no idea what he got himself into" Karen giggled.

"So, let me guess," I said, "you want to wrestle me and if I lose, I get tied up."

"Exactly, and we can do whatever we want." Karen replied.

"So, what do I get when I win?" I asked.

"Well, if you last more than five minutes without getting tied up, I am more than sure that you got your share of grabs to make it worth your while" Karen answered. Laura was listening attentively with a smile that went from ear to ear. I looked up at Pete. Pete too was way smiley.

It was Laura who got up and took my hand. She led me to the living area where the thick rug took the space between the oversized lazy chairs. "Never mind the towel, you are completely dry." she said as she took my towel and tossed it on a chair. Karen was close behind and was already loosening the buttons on her shirt.

It was hard to tell who was more excited, Karen or Laura. I just sat there, on my knees, watching these girls strip in a hurry. Laura was a knockout, that was for sure. But Karen, while older, was definitely worth a second look. Or a third. I could not keep from looking at her. Her firm breasts looked soo much better now she didn't have those conservative clothes on. As she stepped out of typical grandma underwear, I almost gasped. She had shaved too, in the design of a V, as if I needed that type of stimulation.

I looked at Pete. "You are a lucky guy!" I said. "I now know where Laura gets her looks!" I exclaimed. "I bet this is the best kept secret in the valley." I said more to myself as to anyone else while looking at Karen. Pete grinned and was proud as a peacock.

"OK, Pete, You keep time." Karen said as she lunged forward and dragged my head down to the rug. It was a thick rug, with great under-padding, but still I was surprised by Karen's aggression. Her boob was right next to my cheek. I grabbed her around the waist and was surprised how toned she was. While she might have been a light weight, she surely was mostly muscle. I didn't waste any time and while rolling tried to slip my hand up her leg. I could feel the bristle of some fuzz, but not for long as my feet were getting pulled straight away from me.

With a couple kicks I got my feet loose again, but was disoriented with the number of hands grabbing me. I saw Karen's boob flashing by and grabbed what I could. She was firm, with very small nipples, and -maybe I imagined it- she held still for a second while I started to roll her nipple between my finger and thumb.

It was Laura who got a hold of my wrist and yanked it away. She put her weight on it and while giggling said, "There, that teaches you not to be fondling my mom." Oh, sweet goodness, some punishment to see that skinny tan body that close up. And, I still had one hand free. I grabbed her left butt cheek and squeezed it. She giggled some more and wriggled wildly. That only served to loosen my grip and somehow -right somehow- my hand slipped between her legs, felt a bit of a bristle and dove into some soft, moist spot. "AAAAHHHH" she shrieked "He got me!" I knew she was hot, felt hot to wrestle me, but never had expected her to be wet!!

I found a hand starting to stroke me. It took all the strength out of me, it felt soo good. The girls used the reprieve to get themselves situated. I felt some rope ensnare my legs. I kicked but somehow it just seemed to tighten itself. Some weight came off of me and I figured out that just Laura was on me. I rolled over with her even though my feet were tied to something and grabbed her boobs, both at the same time. She giggled. "Mom, you can't leave me here!" she exclaimed. The small breasts were quite the sight, and even more so now I had my hands cupping them. Just as I was starting to deliver a good pinch on her nipples, I found Karen all over me, forcefully pulling me off her daughter.

I reached forward, but my tied feet were holding me back. I held on to Karen, and pulled her closer. After all, I was bent on getting my hands on her breasts, even if it was just for a second. Laura climbed on my back, but with her limited weight, I could still envelope Karen in my arms. I reached for her boobs, but she twisted out of reach. Her twist however, put her lower belly right in front of me. "Oh, AAAHHH" she uttered, as I plunged my tongue between her fuzz.

Looking back, I can't believe I did that, but right then, I didn't have time to think, and took my chance. She tasted way good and again -maybe it was just wishful thinking- she seemed to hold still for a few seconds so I got a good few laps in. With a rough tumble, caused by Lauren, I lost my grip on Karen.

By now, all of us were panting. Both girls were holding on to my wrists, stretching my arms above my head. I rolled over, but it didn't free me. I felt some rope slipping over my hands and suddenly, the girls started giggling as I was stuck! "Haha, got you!" Karen said.

All of a sudden, I realized, we had not discussed what was going to happen next. "So, now you are going to bet my release on if I can hold out for sixty seconds again?" I asked. A lot of giggling was the result. As I was trying to look what was going on, Laura sat on my chest, held my ears in each hand. Karen was nowhere to be seen. I felt something jiggling and tugging on my dick and balls though, so that must be were she was at. It wasn't comfortable, it actually almost hurt, so I moved as much as the ties allowed me.

"Laura, can't you do something to hold him still?" "Can't you distract him for a moment?" Karen asked.

Laura didn't need any prompting. She slipped her hips forward a little, and said: "Stick out your tongue, I know this is what you wanted all along." She smiled, grimaced actually when my tongue actually went in action. I felt something cold on my dick, but never let go of what I wanted to do to begin with. Laura was starting to hum in excitement.

I heard a faint "Click" from behind Laura's body. Karen's face suddenly showed up above Laura's shoulder. "Well, that wasn't exactly what I had in mind when I said distract him!" she said in a scolding tone.

Laura got off of me. I looked at my dick. I yelled out: "What the hell is that?" Some type of steel contraption was over my dick and a ring was around my balls. The click I heard earlier must have been the little lock that seemed to hold it all together.

Everybody laughed. Except me of course. Karen said: "that is a chastity tube." "It will keep you pure."

WTF, I didn't want to be pure. I didn't want any of this. "Let me out of here!" I exclaimed.

Karen replied: "Oh, you agreed we could do whatever we wanted after we had you tied up." "And since Pete and I will be out of town for a few days, we thought that this would take your mind off of little boys thoughts and help you focus on your work." And while she looked at Laura, she added: "And it would make sure you wouldn't get into any trouble with her." I was ready to throw a fit. "Tut, Tut, cool down." Karen said. "We will untie you, but remember I have the key," as she lifted the fine silver necklace around her neck with a tiny key dangling from it. I couldn't believe that this whole time she was standing next to me, talking, I was laying on the ground with the best possible view.

Karen was obviously enjoying it. My dick was straining against the tube and Karen just had to point that out. "You will find that quite uncomfortable, being aroused. But when you are calm, you will barely notice your little friend in confinement." She said.

They undid the ropes, while I got a few last glances at the scenery which I would have really enjoyed if I wasn't in the predicament I was in.

Karen said: "Now be nice, and work hard. We will be back on Friday, with the key, and will set you free, if you behave." I gathered my things and got out of there.

While starting my truck I said to myself, and how, just how do I get myself into this kind of trouble?

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
mrwidehorizonsmrwidehorizonsabout 9 years ago
Love it!

I love chastity stories and this one is so hot and original I gave it a 5!!

AnonymousAnonymousabout 9 years ago
LOL

This guy is such a douche. I picture a Lou Costello schlub of a half assed "handy man" bumbling from scene to scene with the family each week in an R rated comedy on Cinemax. Looking forward to the next episode.

MasterfuljimMasterfuljimabout 9 years ago
Nice thought

I'm sure a handy guy like him will remove it in ten seconds flat.

Share this Story

Similar Stories

Kidnapped and Milked Nurses drain their subject of his essence.in BDSM
Flagpole of Humiliation Babysitter takes control.in NonConsent/Reluctance
Any Other Port In A Storm He is saved in a storm, but his hostess has plans for him.in NonConsent/Reluctance
Her Science Project Ch. 01 John helps his roommate Jenny with her psych project.in Mind Control
The Sleepover Woman takes advantage of sleeping man.in NonConsent/Reluctance
More Stories