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Introduction:

This a story of the first time I particapated in bondage
Intro to Bondage
The other day I caught myself day dreaming, for whatever reason I got to thinking of my first summer after high school. I was 18 and I was ready to experience life.
Even though I was working full time at a local burger joint, I had plenty of free time. One afternoon I get a call from my mom asking me if I wanted to do some yard work for someone, after I said yes, she gave me the phone number. I called to see what they needed done. I was given the address, told that they had everything except a strong back basically. She told me it was too late that day and asked if I could be there first thing the next day. I said at the crack of dawn yes.
The next day, just as the sun crepted over the horizon, I pulled onto the drive way which was about a quarter mile long; I could only admire the house.
I knocked on the door; my new boss answered the door. “You were not kidding about the crack of dawn”
“Yes mam”
Don’t call me mam, I’m not that much older than you.
Sorry, it’s the way the I was raised,
No problem, I just wish more were raised like you.
She showed me what all needed done, and where the tools were, I got right to work.
On the back of the house, they had a pool that was screened in. I would glance in the direction, not wanting to look like I was trying or anything, none the less; I couldn’t see anything in there.
It took a few hours, but after I was finished, Donna thanked me and paid me very well, she invited me to stay and swim, but I had to get to work.
About the time I got home, I get a call from my mom, saying that Donna wanted me to call her and she gave me their number.
When I called, Donna said that her sister, Jenna wanted me for something, I told her I could be there about the same time, she asked me to get there around 8:30.
The next morning, as I was getting out my car, she walked out telling me she had to get to an appointment, and that Jenna was at the pool waiting on me, she told me to head through the house to patio. As she got into her car, she seemed to make it a point to tell me she wouldn’t be back till around 3:00pm
When I walked onto the patio, she was relaxing on the lounger wearing a very sexy black bikini.
She handed me a list of things she wanted done, I looked at it as I walked to the shed to get the tools.
It only took me about an hour to get everything done, I walked onto the patio to tell Jenna I was done, looked like she hadn’t even moved from when I got there.
Here is your money for today, her pointing to the bottom of her bikini, no hands allowed in getting the money, the money was rolled up, and sticking out the top. I bent down and grabbed it with my teeth; I kissed her belly while I was down there.
As I stood up, she sat up starring at the bulge in my shorts. Looks like someone is awake.
I bet you got your share of pussy while in high school.
I got some. Yes.
Shit?
She reaches up and starts to rub my cock through my shorts, and then before I know it, she unsnaps my shorts and pulls them down, my rock hard cock bounces once it’s freed.
I’ll make a deal with you.
If you can last 30 minutes without Cumming, I will let you fuck me till you can’t handle it.
I start running through my head what all she could do; I said it’s a deal.
Great, go to the back side of the shed, get the whole sheet of what looks like peg board and bring it to the living room.
As I start to turn, she tells me to step out of my shorts and to pull my shirt off.
I was glad we were out in the country, I jogged out to the back of the shed, I saw what she was talking about, and it was a whole sheet of heavy peg board. With 2x4s framed around it, with hinges towards the middle, I picked it up and started into the house. I get it into the living room; she instructed me where to place it.
She had me lay down on it. She placed a set blind fold on me now just relax while I get everything set.
Then she starts to strap me down
When she was finished, I couldn’t move a muscle, she had everything bound, my head, hands, feet, even my hips.
After what seemed like forever she removed the blind fold, she was wearing a black leather or vinyl looking teddy. Hose and heels.
She pulls on two ropes sitting me up.
Here is how it’s going to work out, I am going to tease you to death, and you might even call it torture.
If you can hold off Cumming for 30 minutes. I will then give you a few minutes, to calm down, and then will ride your cock until you beg me to stop. If you cum before the 30 minutes is up. I will stop, let you clean up, and then leave.
I could only say, let’s run it.
I was hoping you’d say that.
She started by first stroking my cock really slow, using a lot of some sort of oil. Rubbing from the base of my cock up over the head, almost like she was trying strangling it.
I kept trying to pivot my hips, but she had me tied down. I was completely at her mercy and it was an incredible turn on. Just as I thought I couldn’t hold out any further and was about to blast a load of cum from my cock, she would pause and rake her nails up the length of my cock. Pausing for a moment only to rake a metal tracing wheel the entire length, for the base of my balls, to the tip of my head.
I was loving the mixture of the pleasure with the pain.
All of the sudden she stopped got up and walked out of the room, only to return with a bag of ice and place it on my cock.
All I could do was moan in agony.
I so wanted to blast her with a load of cum, but I wanted to last as long as I possibly could.
After a few minutes with the ice on my cock, she removed looking at my now soft but hardening cock.
She stood over with her legs spread,
Get your cock as hard as you can without my touching you. You only have oops, I forgot to start the timer she had the most devilish grin on her face.
Once I harden myself, she knelt down, and tied a string around the base of my cock, and then my balls.
She tells me to sit up; I try but can’t really do it.
Here, let me help, she reaches down, grabs something from out of my sight, and clamps them to my nipples. (Yes my introduction to nipple clamps). After she clamps both of them on, she pulls the string.
Now sit up. I somehow manage to sit up.
Once I sit up, she lets go of the strings, “Now stay like that”.
She straddles my face, “Lick it”.
I stick out my tongue as far as I can.
Splitting her Pussy lips, and penetrating as deep as I can.
“Oh god, what are you, part horse or something”?
I had always thought I had a rather large tongue.
She kept putting so much pressure on my face; I was flat on my back quickly.
Just as I was starting to enjoy eating her Drenched Pussy, she stands up.
Wow, you have a future in that young man.
She starts stroking my cock, almost like she was wanting me cum. Just as I was about to blow, she stopped, and after a pause started running the tracing wheel over my cock.
When I snuck a peek, it looked like a tracing wheel that I had seen used before, but this had larger pins coming off.
All of the sudden, she tells me “ok, that’s close enough”.
She stood up, time for a bit of a break, and then I’m going to ride your cock, as much as you can handle. She reaches down and unhooks the nipple clamps; I could not believe the pain from her taking them off. After removing the clamps, she seemed almost like she forgot about the string tied around a cock, she reached down and untied it, and it almost felt like I was pissing cumm. She rubbed my cock, scooping up some of the cum. She placed the finger in her mouth.
“I love the taste of cum in the morning”
She walked out of the room, leaving me where and how I was.
I thought to myself, “great, I was about to blow the biggest nut”.
A few minutes later, she walked back into the room.
OK, you lasted 30 minutes plus, with me torturing and teasing your cock.
I replied “I have no idea how, I will be honest, I was about to blow when you stopped”.
Now I am going to ride your cock until you say stop.
My cock hardens up just from the anticipation.
Someone is ready to go. She reaches down and re-attaches the nipple clamps. I almost beg her not to. I grimace in pain. But I loved it at the same time.
She then reached up and pushed a couple thumb tacks into the ceiling with yarn attached to each one coming down to the corners of the board; she has me sit up some, and ties the yarn to the corners.
Now hold it there, don’t let the tacks pull out. She straddles my cock, facing away. And rams my cock into her and starts to ride my cock.
For some reason, I wanted to smack her on the ass. She kept riding and I kept enjoying,
Finally, I moan “I am about to cum”.
Not yet, she pulls on the string attached to the nipple clamps.
I have no idea why I couldn’t cum. I guess it was the pain from the clamps, my sitting at the angle, and trying to make sure the tacks stayed in the ceiling.
Before I know it, Jenna starts to tense up, before I know it she cums.
All I could do was say, don’t stop. I was still strapped to the sheet of re-enforced peg-board.
She stopped for a moment to rest and I guess to gather herself. She reached down she rubbed her pussy with her one hand, turned towards me.
Open your mouth, she put two of her pussy soaked fingers in my mouth, I started lapping it up. Loving the flavor.
Are you ready?
Yes!
I so wanted to cum, but I also didn’t want for this to stop and I thought that as soon as I came, it would be over.
She started rocking on my cock, first slowly and slightly, then more forceful. The harder she rocked, the closer I would get to Cumming. For some reason I could not cum.
I know she got close to another orgasm, she stopped stood up.
In a very angry voice “WHAT THE FUCK’S THE PROBLEM?!”
What do you mean?
“IM PUMPING THE HELL OUT OF COCK, AND YOU DON’T SEEM EVEN CLOSE TO CUMMING!”
“I really think it’s the clamps, and having to sit up.”
She looked and noticed the string still attached to the ceiling. “OH SHIT, I CANT BELIEVE YOU HELD THEM IN”
She faces me, straddles my cock, and kneels down, my rock hard cock slides easily into her drenched pussy.
I’m bound and determined for you to cum. She started pumping my cock in and out. I was so close to Cumming, but I just couldn’t.
All of the sudden she leaned over and started sucking on my neck, like she was trying to put a hicky on me. And then she add pain to pleasure, she reached down and twisted one of clamps.
As much as what she was doing to my nipple hurt. I was about to bust a huge nut.
“I feel your cock swelling, now fill me up”
She kept pumping; I knew I was about to bust. All of the sudden I couldn’t hold back anymore. I let go, and shot rope after rope of cum into her. This orgasm was so intense, it felt like my shins cramped up. She did her best to not break rhythm but she couldn’t. She had to stop.
She pushed me back pulling the tacks out of the ceiling, and then she removed the clamps. Not allowing my cock to slip out of her pussy.
“You get hard and I’ll keep pumping. With the pain portion no longer a concern, and her very slight movement. I was rock hard almost instantly.
“that’s what I like” as she started pumping my cock’
You can cum all you want, I’m fucking you until you either go soft or can’t handle it anymore

I still couldn’t move even a little. She would not un-do any of the straps.
She continues to pump my cock, and suddenly, I was Cumming again, shooting a couple hard ropes into her.
This time she really concentrated on the head of my cock, trying to touch only the head of my cock.
I could barely handle it; I could not believe how sensitive the head would be.
She somehow spun around using my cock as a pivot. I so wanted to pump my cock, but I still could not move even slightly.
I could see her ass bouncing up and down on cock, I knew I was in her pussy, but it looked almost like I was butt fucking her.
Suddenly, I start to tense up, I cum yet again. This time it was too much. She thought I was having a seizure the way I twitched and jerked.
Are you ok?
She looked worried, when I gathered my composure; I was able to tell her yes. It was an extremely intense orgasm.
I ask her to untie me.
You had enough?
Yes, for now.
She unties me; I stand up working the stiffness out.
At first I was not sure if I wanted to thank her or not.
I decided to, “Thank you”
She asked for what
“For the fuck of my life”
“You are young, with your life ahead of you, I’m sure you’ll have good fucks”
She tells to take a dip in the pool.
I jog over to it, jump in, god it was cold. I try and swim a lap or two, I had no energy. I decided to just grab the pool toy and float.
I pulled myself out after about 30 minutes; I asked if she needed me for anything else.
She asked me to put the peg board back. I did so without even putting my underwear on. As I walk back into the house. Jenna asks me when my next day off was.
I said Monday.
Good, plan on coming out Monday morning; I will have a surprise for you.
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