Failed Escape Challenge
  • Author - tommiebuoy
  • Rating -   
  • Site Rank - 2722 of 2955
  • Story Codes - M-f, consensual, analplay
  • Post Date - 2/1/2021


I had a crush on Gloria since I was 11 and met her the first time. Her then-husband worked for my folks'construction company, and I met her at 4th of July BBQ they had. Gloria is blond, large- breasted, nice round ass just beggin to be patted, luscious lips to kiss (or do other things), and gorgeous. She and her ex were also friends with my older sister, and when she got married, they were at the reception. Gloria was dressed to "the nines", tight blouse with just a bit of cleavage, tight skirt hugging that delicious ass, hose, and stiletto heels. The heels made her taller than her husband, which ws one of the issues causing their marital discord. Her husband just wanted to sit and drink, Gloria wanted to dance, and other than me, there were no unattached males. So, her husband asked me to dance with her. It was heaven on earth. Holding her close, feeling her memorable boobs against my chest, wowza! Couple of time we even kinda rubbed crotches, and twice, she rubbed her ass against my crotch. Yep, it gave me an instant hard-on. Fast forward about 5 years, I was now 21, and out on the town with friends celebrating my 21st birthday.

Gloria was at the lounge we went to, apparently out with several of her co-workers. By now, she was divorced, (I knew that), still breathtakingly gorgeous, but also completely unattached. When her group found out it was my birthday, they kind of joined us (6 guys, no dates), and we had a grand old time dancing, and drinking, and laughing. When we go ready to leave, Gloria told me friends that I couldnt leave with them, as all had been drinking, heavily, and as a family friend, she would get me home. (She had been drinking also, but that kind of went past us). With little argument from any of them (I lived in the country, all of them in town, so not having to drive out to "the sticks" appealed to them. Gloria had an older car, I think 70s or 80s, that was enormous, so I loaded up with her and 2 other ladies, who she soon dropped off. On the way to my house, she asked me if kids still went to the reservoir to make out. Apparently that had been THE spot when she was in school. I told her. no, the county fenced it off. She then asked where kids went to make upit nowadays. Feeling no pain, due to my celebrating, I didnt realize the angle she was taking. By the way, Gloria is only 7 years older than me, same as my sister. I told her I didnt know where others went, but I had a really good, hidden spot, and no one ever bothered me there. She had me tell her where it ws, and shortly, we were there.

By nnow, the booze was wearing off a bit, and I was thinking much better. So, I asked her why all the interest in make out spots. She very politely informed me she wanted to give me a birthday gift. So, she did (actually 2-the best blowjob I'd ever had up til then, and then, in the back seat of that huge Pontiac, 45 minutes of great sex. As she headed out for my house, still with her blouse and bra off so I could see those magnificent tits of hers, she then began talking about tie-up games she played when a kid. I told her my older sister had played some with me and my brother, she told me that she knew that, thanks to my sister relating her experiences. She also told me my sister had told her I was better at tying than y brother who is 4 years older. Thats when she asked if I would like to get tgether and play tie-up games with her. Of course, I said yes. By the time we arrived at my house, we had set a date and time to hook up.


I spent the next day going to a hardware store, and retail store, a drugstore, and a home improvement store, acquiring supplies. At 6pm that night (Satruday), I knocked on the door of her apartment, and she opened the door. I was a bit disappointed when I saw her, as she was wearing a t-shirt, jeans, and flip-flops. She obviously realized it, and told me, "relax, this is just to travel in. I've gpt a bag with what I need."

She then informed me that we were going to her parents' clubhouse about 10 miles from town, on a private lake, but no one would bother us. We loaded into my truck, with her bagin the backseat (it was HEAVY), and off we went. When we arrived, she handed me the key, I unlocked the door, carried in her suitcase, put it in one of the bedrooms, and she told me to grab a drink while she got ready. 30 minutes later, she came out of the bedroom, and my jaw dropped! Her blouse was so sheer, she might as well not worn one, because it concealed nothing. Plainly visible thru the blouse was a black shelf bra that lifted those gorgeous tits but didn't cover them. Her skirt was tight, about 5 inches above her knees, and what I thought were black pantyhose turned out to be stockings, held up by a garter belt. She wor no undies, and had shaven her pussy since our previous hook-up.

She had on black stiletto pumps, (her trademark dress-up footwear), and had no jewelry on. Sshe proceded to tell me to tie her as good as I could, no restrictions. However, she intended to work as hard as possible to escape. If she escaped, we would go back to town, I would drop her off at home, and that would be it. No more hooking up, nothing. However, ir whe failed to escape in a predetermined time, 30 minutes, I was freee to do whatever I wished. Not just that night, but anytime. Just call and say where to meet me, and it would happed. So, obviously, I was motivated to excell.

I bound her wrists, just above the wrist bone, wrapping several wraps, then tightly cinching, then the same to her upper arms, which had the double effect of pulling her elbows together til they touched, and pulling her shoulders back, causing her big tits to thrust out. I also tied her forearms, just below the elbows, then, when I went to gag her with a new sponge, she told me she had some gags in her suitcase. I went in the bedroom, and brought her suitcase out. The reason it was so heavy, she must have had 2 miles of rope, several rolls of vetwrap, and gags, and some adult toys. I picked the cock gag, and when I held it in front of her, she said, "I might have known you'd pick that one", but her eyes were twinkling. I pushed it between her luscious lips, buckled it tightly, then taped her eyesvertically, then horizontally. I led her into the other bedroom, where there was a queen size brass bed. I helped her onto the bed, rolled her onto her tummy, and tied her ankles to her thighs, then hogtied her. As a final step, I wrapped all ropes with the duct tape I had brought. I told her to begins struggling, and I would tell her when 30 minutes were up. I actually waited 40, because I enjoyed her struggling.

My cock was so hard, it hurt, and after announcing time was up, I removed the gag and sked her if she needed any proof of the time. She said she didnt, she admitted she lost, and she was now mine for whatever, whenever, as long as I was interested. Thats when I pushed my cock b etween her red lips and she began sucking instantly. It took about 2 minutes, and I blasted the largest load of cum I could ever remember discharging down her throat, which she dutifully swallowed. I offered her a adrink, and after she had satisfied her thirst, I released the hogtie but not the frogtie. Pushing her knees apart, i knelt between them, causing her to say, "so, youre gonna fuck me like abitch dog, huh?"

Still blindfolded, she couldnt see the tube of lube I had; I was gonna fuck that delicious ass I had lusted over for years. Since she wore no panties, I just pushed up her skirt, pulled her back a bit so her knees were under her, then squirted some lube onto her buttcheeks, and when I began working it into her tight,puckered ass , she said, "really"? I worked quite abit into that tight opening, causing her to squirm a bit, but she wasnt complaining. Finally, I pushed the head of again rock hard dick against the "exhaust port" and began entering her as gently as I could and still make ssome progress. She moaned and groaned a bit (quite a bit, actually), and let out a yelp as I fnally went "all in". I gave her a minute of 2 to adjust ands stretch, but finally began thrusting; slowly at first, then faster and hard until I was pounding tthat ass like a wild man. I filled her shit chute with another load of jizz, then went to the bathroom and cleaned up.

When I got back to her, I asked if she needed to be untiedd, and she just asked to have the blindfold removed. Looking at her, in no time I was hard again, but this time, I rolled her onto her back, on top of her bound arms, and with out a word of warning, buried myself full length into her woaking but tight pussy. Much slower this time, as I wanted to enjoy her tits, but after 15-20 minutes, I got going hard again. One more load, and I told her we had to take a break for a while.

The End
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