The First Time

Story Info
A mature male is tied and taken anally by a stranger.
1.7k words
4.35
37.3k
18
5

Part 1 of the 3 part series

Updated 06/08/2023
Created 10/22/2016
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Well, when I was very young on the farm my 2 older brothers used to tie me up & leave me in the haymow until they decided to come & get me. Later I started doing it to myself-only naked. A couple of times I almost had to call for help as I was swinging from a rafter tied by my wrists & couldn't take the pressure off of the ropes in order to free myself. Sometimes I hung there for a while.

When I traveled for work I met a lady who lives far away. We are both married but craved something different. Sex was great and eventually we tied each other up - or down- and I found that I enjoyed being tied more than tying her up. I am a bit of an exhibitionist and began wearing some of her panties but she was very small and so I developed my own wardrobe and sometimes I would give her a fashion show.

She would tie me up or down whip me a bit, pinch my nipples and eventually she did my mouth and ass with a strap on while calling me her slut-which was amazing. It was so sexy & wild. I can't get those images out of my head. Me bent double over the back of her sofa with my ankles tied to the outermost legs and my wrists tied to the front ones. She would stick her cock in my mouth and I'd get it very wet before she slid it up my ass while slapping my thighs.

I have numerous Polaroids of these sessions which are dangerous to keep around but I just can't bring myself to burn them. Unfortunately both of our circumstances have changed and we can no longer get together.

I advertised on Craig's list several times for a lady to take her place but got no takers. There were few opportunities for a man my age and with my fetishes to get any sort of satisfaction.

I began to fantasize about having a man actually fuck me since I had taken a strapon up the ass. So I changed my ad. The title read "Submissive first timer" into cross dressing, anal and bondage. I have fantasized about being taken orally and anally by a man who has 'captured' me and would really like to have this experience. I have had oral sex with a man years ago, but would love to have a cock up my ass and and in my mouth under the right circumstances .

That got some results and one of the first only lived 10 miles away. After emailing each other for a few weeks we got the opportunity and I got the courage to meet at his place one morning while his wife was out. He liked ladies lingerie too- specially pantyhose and so I got some clothes to match his attractions.

I shaved practically all of my pubic hair off and buzzed my legs & thighs. I took 3 enemas until I was clean as a whistle. I inserted my silicone butt plug and put a leather ring around my cock & balls. I placed my wardrobe in a shopping bag & drove to his house. It was all alone at the end of a long driveway out in the country. The door opened before I could knock and he let me in. He was a few years younger than me, a little more hairy and well proportioned.

After some talk and a drink we decided we should try it to see what happened. He left to get dressed and I went to the bathroom to do the same. I opened a flask and took a big gulp of Vodka I'd brought with me, put on a black snap thong and covered it with a garter belt and fishnet stockings. A chain with nipple clips went on top covered by a see through black camisole that just came to the top of my ass in back & the thong barely covered my hairless cock. I pulled on my black leather pants and zipped up my black leather jacket, and slipped into high heels. I then placed a leather collar, and nylon bracelets & anklets on, each one with a chrome ring fixed in it. and put on a pair of dark sunglasses. Stupid I know but my first time, right?

I asked through the door if he was ready and he said yes. I opened the door & stepped out to see him standing there in a pair of patterned panty hose and a silk blue top. "Looking good!" I said. He answered "so do you, what you got under there?"

I said "come over here & take a look." I slowly unzipped the jacket to let him see and he came forward to feel my chest & pulled lightly on the chain. I moaned in spite of myself. I removed the jacket & said the rest was up to him. He unbuttoned the fly of my leather pants & slid them down to my ankles. I had to kick off the shoes to get them off. He then told me to slowly turn around which I did as he said "Nice ass!"

"Thanks "I said- "Yours if you want it". I walked around him and caressed his ass through the panty hose and reached around to stroke his hard cock. His hands reached around to grab mine which responded instantly. We felt each other some more until I took the initiative and dropped to my knees in front of him. Slowly peeling down the panty hose I licked his shaft and then plunged his cut cock in my mouth and sucked hard. It became clear he would not last long so I asked what he wanted to do & where he wanted to come- in my mouth or ass- both if he could manage. He said he wanted my ass and god I had fantasized so long about getting to feel a real cock in it!

I reminded him it was my first time with a man and that I was very nervous in spite of appearances and that was what the ankle and wrist bands were for- in case I chickened out. I wanted & needed to be tied down. He had a kitchen table that would do nicely. I bent over it and handed him 2 pre-cut pieces of soft pliable nylon rope. He deftly fitted an end through the steel loop on my left wrist and around the top of the left table leg in front of me an pulled forcing my chest to the table top. Then the rope went around the right front table leg and through the right wrist loop and he pulled them tight before tying a firm slip knot. No turning back now, I was his.

He followed the same procedure with my ankles until they were spread very far apart to the other 2 table legs. With my high heels on my ass was the perfect height for his bobbing cock, but first he wanted me to suck on it some more which I was perfectly prepared to do. I feel like my amateurism was outweighed by my enthusiasm and soon he was almost ready to burst.

Then he came around behind me and unsnapped the thong. Noting that I was already occupied, he slipped his fingers around the base of the Butt plug and slowly slid it out of my ass.

"I wonder where this could go?" he said, and stuffed it in my mouth securing it with a strip of duct tape. I felt him lube up my ass, inserting first one and then 2 fingers and heard the foil come off the condom we had agreed upon. I felt the head of his cock press against my puckered ass hole and he slowly pushed home until the swollen head entered and continued until I could feel his pubic hair against the crack of my ass. He held it there in the heat and tightness for a moment and then began to rock back and forth. With each forward thrust my pubic bone ground against the table edge and I moaned around the plug in my mouth and my semi hard cock slapped against the table bottom.

He grabbed my hips and thrust frantically a dozen times or more until I could feel his spasm and then he laid on my back breathing heavily. After a few minutes, he pulled out of me, slid off the condom and walked in front of me. He held me by the face and withdrew the butt plug from my mouth and replaced it with his sloppy cock which I sucked to erection in no time flat. He held my face with both hands and fucked my mouth until he came a second time. I swallowed it immediately- (swallow don't wallow) not as large a load as the one in the condom in my ass I was certain. Then he went into the kitchen and started to make coffee, leaving me spreadeagled over his kitchen table panting and trying to get some stimulation on my cock.

"Hey man", I said "what about me, I'd like to come and these nipple clips are starting to hurt."

He turned and forced the silicone cock back in my mouth, and secured it with a wide strip of duct tape. He said "What a great ass, he said, I think I'll keep it right here until I am ready to fuck it again- which won't be long!" Hen put his coffee on the table in front of me and then began slapping my exposed ass with one hand while he reached under the table and began to stroke my now hardening cock.

I heard the click of a door latch and heard a woman say "Well, well what do we have here? Looks like a whole day's entertainment. She dropped grocery bags on the floor and walked around me on the table and slid her hand over my body and kissed her husband. I still had the stupid sunglasses on with dildo taped in my mouth and the fishnets and garter belt and was spread wide open on her kitchen table. "Wait for me while I get my strap on"! "Oh, and I noticed that Bill & Mary's car is in their driveway, why not call them over to give us a hand with our new toy?!"

She left the groceries on the floor and headed to the bedroom.

To be continued...

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  • COMMENTS
5 Comments
hotwillyhotwillyover 5 years ago
First time

Great start, especially with promise of Part 2

Never had the pleasure of being subjected to such bdsm, but reading this story I would certainly be happy to change places, thanks

whiplegagwhiplegagabout 6 years agoAuthor

I have been told that "the first Time" may not be a suitable name for this story and that is a fair comment as most would view it as happening to a younger person- but in this case, not so much!!

part 2 is coming...

whiplegagwhiplegagover 7 years agoAuthor
thanks for reading

I have many more in this genre, and although I believe that my characters use best practices in keeping with the characters, it is a fictional work.

AnonymousAnonymousover 7 years ago
Liked it

Well I liked it :)

Deejay121Deejay121over 7 years ago
Not my thing

this is in the wrong category I believe sorry

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