I Dare You

I dated Kay in grad school. While the “Soxer” was 11 years older than I was, she was fun to be with at times and had a wild streak in her when it came to sex. She liked to role-play, have sex in interesting place, loved to exchange fantasies, and watch porno together. The best thing was that she could deep-throat me and I am not small (a little over 7.5 inches).

She liked to suck my cock and liked it when I came in her mouth. Kay was 5’9″, 140 pound. She had 38c tits and a nice pussy. I am a little over 6’00”, about 175 pounds. She said having sex with me was fun for many reasons but mostly because I have an adventurous spirit and I could make her have an orgasm by licking her pussy.

The Soxer had an aunt and uncle who lived about 45 minutes away, and we visited them several times while we dated. Once, on a hot and humid early evening on our way back to school, we stopped on a small side road in heavily wooded area and practiced “parking.” I had never done this before but always dreamt about it. We started off hot and heavy in the front seat (my 2-door car did not make the back seat conducive to these activities).

While I played with her tits through her button-down shirt, she massaged my dick. Eventually we stripped off our shorts and began to fuck, but the steering wheel began to cramp us. I backed out of the car and she hung the lower half of her body out of the car. I rammed my cock in and out of her causing her pussy to get hotter and wetter.

I pulled her out of my Fairmont and leaned Kay up against the car and penetrated her again. She wrapped one, than both of her legs around my body-I kept her pinned against the car while I pumped in and out of her for a few minutes. Wrapping my arms around her, I picked her up and slowly walked toward the hood.

All this time, I kept my cock inside her. Once at the hood, I lay her back and started fucking her hard. My hands drifted to her tits (still enclosed in her shirt and bra) and eventually Kay’s clit. She began to breathe harder and harder until I knew she was on the edge of cumming. I sped up my strokes, pulling my cock all the way out and slamming it back in. She came. Her body gyrated. She sighed over and over “Oh my God! Ohmygod!! How can you do this to me?!!” It was beautiful.

I left my cock in her for another minute or so. After pulling out, I was still mostly hard, but had yet to cum. After a moment of rest, Kay came alive. She sat up and after kissing me, softly said, “Thank you. That was one of the best orgasms I have had in a very long time. I guess it is time to take care of you. How can I get you off?”

I whisper back, “I want you to suck my cock. I want to cum in your mouth.” She kissed me and slid off the hood. Kay knelt before me. She softly held my cock, wet from her pussy.

Looking at me in the eyes, she said, “You like it when I lick your cock, don’t you?”

“Yes,” I hissed. She circled her tongue around the head of my dick. As I grew to full size, she slid her mouth along the sides of my cock, cleaning her juices off. Then she started to suck on my cock. At first, the Soxer just put my head in her mouth and circled her tongue around my head. The whole scene was sexy; both of us without pants, but still wearing our shoes. Me with a t-shirt on; her shirt unbuttoned about half way. Kay with my dick in her mouth. Just thinking about it made my harder. I asked, “What if someone drives by?”

“Let them watch to see how it is done correctly.” She took my cock deeper in her mouth with every pass. Eventually, she shoved the whole thing in her mouth. I felt my member hit the back of her throat and continue down. She could only hold it there for a moment or two, before she made me back out. I placed my hands on the back of her head and played with her hair. Eventually, I started to fuck her mouth. My orgasm approached. As I got to the “point of no return,” I pulled my cock from her mouth.

While pulling on my own dick, I held it about four inches from her still open mouth. I came. I came in 5 big squirts. The first landed mostly in her mouth. The second hit just under her nose. The third, on her chin. The fourth and fifth I sprayed on her neck and down her chest. She swallowed, then put my cock back in her mouth and sucked me dry. After she released me, still on her knees, she looked up and smiled. I will never forget that scene: her mouth, chin, neck and chest sticky with cum.

Slowly she stood up. We kissed. I actually like the taste of my own cum, so I licked her chin and around her mouth. We parted, “I guess we had better get back to town.” I don’t know if she did it purposely, or the humidity just fooled into thinking it was just sweat, but the Soxer did not clean my cum off her neck and chin. In fact, some of my cum soaked into her shirt. She attempted to button up her shirt but I stopped her. “Leave it unbuttoned like it is,” I said.

“Aren’t we stopping at the supermarket on our way home?” she asked.

“Yes. But I want people to see your big tits, lust after you and be jealous of me.” She looked a little hesitant. “I dare you.” We were always doing these little dares.

“Okay, but I have a dare too; I dare you to leave your underwear off.” I agreed.

We dressed and drove back to town. We glowing and feeling pretty giddy. The humidity did not allow my cum to dry on her neck and shirt. At the supermarket, I noticed how both men and women looked at Kay. It was obvious that she was covered in cum. Some gave look of disgust, but most looked at her with lust. Several guys spent a lot time examining produce while she leaned over while picking out apples. I even got a thumb’s up from one guy.

My cock started to grow again. As we proceed through the store, she kept making me examining items on lower shelves. As I squatted looking at some cans of soup, my dick slid out of my shorts. Kay was staring at me with a big grin. She was enjoying my display. We moved to the next aisle, and I did it again.

This time, the Soxer whispered in my ear, “I love seeing your cock. This is really turning me on.” Two aisles later we ran across a friend of Kay’s from church. She was a very attractive woman in her mid- forties named Trish. As she smiled, she asked what we had been doing, all the while staring at Kay’s chest and neck. “Oh nothing,” Kay said with a wink.

Being a little brave, I decided to give her friend a little show. I squatted and began to examining some items. My now rock-hard dick sprung out. Trish stared and put a very big smile on her face. I stayed down for a good two minutes. After which, she said in a hush to Kay, “You are so lucky to have a boyfriend like CJ.” And then she winked at me. We parted. Kay kissed me. Once we got home, we fucked like rabbits.

Several weeks later, we returned to Kay’s relatives. Although we did not discuss it overtly, we both want to repeat our previous encounter. To that end, I asked her to wear only a loose fitting tank top with a plunging neckline, and shorts without underwear. She made me wear a similar outfit-tank top and the same shorts that I wore before, without underwear of course.

We couldn’t be dressed like that at her aunt’s, so we each wore a shirt over the tank tops. Because we were only eating an early dinner with them, it was not necessary to wear different shorts. Departing her aunt’s, we both removed our shirts, and played each other’s chests through our shirts. I could tell that she was hot for me. I was equally excited for my cock had already sprang to action.

She took a different route back to school, and had little luck finding an isolated road. With light fading, we got on I-94 with disappointment in our faces. As the Soxer drove, I reached over and began to rub her inner thighs. After a few miles, she exited the freeway. “Why are you getting off here,” I inquired. “I thought we might pick up a video.”

I looked up, and realized that she had pulled into a XXX shop. Its parking lot was more than half full. “Kay, are you sure you want to go in there?”

“What, CJ is getting chicken?”

“Well, I am just concerned about you,” I lied; I wanted to go in badly, but I did not want her to feel she had to.

She looked me dead in the eye and said, “I dare you.” That was all I needed.

We got out of the car and walked toward the entrance. Kay still wore only the tank top, shorts and shoes. The signs on the front door warned that “You must be 18 to enter.”

“Ah-oh,” I said, “do you think we should bring our ids?” She giggled and just opened the door. We walked into a bright room full of sex videos and “marital aides.” All the 8 guys in the store looked at us while we examined the titles. Kay and I would showing each other video boxes with silly titles like “Edward Penis- hands,” and “Sperms of Endearment.”

We giggled quietly with one another. At one point, I quietly said to her, “The other customers are staring at you.” She grinned. “I dare you to lean over and let them see down you shirt.” She looked at me and winked. Moving down the aisle about 5 feet, bent over at the waist to look at some titles. The guys almost drooled as they looked down Kay’s shirt at her big tits. She did this about 3 times until all the guys had been flashed.

She returned to my side with a devilish smile on her face. “I want you to squat like at the supermarket.” I was a bit hesitant; flashing women was one thing, guys was another. “I dare you,” the Soxer said. I proceeded to the next aisle and squatted down. My dick popped out of my shorts. The two men in my aisle gazed at my cock. One smiled. Like Kay, I made sure I flashed everyone in the place.

We were getting a little bored looking around, and then I spotted the hallway, which lead to the “Private Viewing Booths.” I had visited similar booths like these once or twice before. I found them to be very exciting. I motioned to Kay and nodded toward the hall. She had a puzzled look on her face. I whispered in her ear, “I dare you.”

She smiled and nodded yes. I got $5 worth of tokens from the store attendant. The hallway was dark. On either side were 7 booths. One or two guys were hanging outside in the hall. Most of the booth’s lights indicated that they were being used. The noises of the videos filled the area. We proceeded down to end of the hall and chose the second from the end on the left.

The little cubicle was crammed and dark. After closing the door, we put the seat down. Kay and I were able to sit side by side. I put the tokens in the illuminated slot. The video screen sprung to life. The opening film was of a woman being fucked doggy-style. Her huge tits hung down and shook as the man pounded in and out of her. Kay changed the channel. Looking around the booth, I notice holes at crotch height on either side wall.

I knew instantly that these were “glory holes.” I had read about them but never seen them before; they always fascinated me. Kay settled on a movie that showed a big-titted woman surrounded by 3 guys. While she sucked one, she jacked-off the others. Kay’s breathing increased, as did mine. I began to massage her thighs and rub her tits. I nibbled on her neck, all the while watching the screen.

Slowly, I moved my hand down to her pussy. I rubbed it with the palm of my hand. The Soxer now grabbed my cock through my pants. I pulled her shirt up and began to knead her tits. Eventually, I lifted her shirt off. She pulled my dick out. I pushed aside her shorts and began to finger her.

I could tell that Kay was getting very excited. I crouched down in front of her, put my tongue in pussy. She moaned and kept her eyes on the video screen. I worked her clit over while sliding 2 fingers in and out of her. After a minute or two, I could tell that her orgasm was approaching. I speed up my tempo. Kay came hard, bucking on my face.

After a short rest, she looked down at me with a smile. I sat back up on the bench on top of her shirt. With her big tits swaying as she bent over, Kay began to change channels. Eventually, she stopped on a gay movie showing some guy sucking on a very large cock. She had always been turned on by gay stories. I had confessed to her that I had always wanted to try sucking a cock. While we both watched the movie, she stroked my very hard dick. She said in my ear, “You want to do that sometime, don’t you?” I smiled at her.

Suddenly, as if on some cue, a cock came through the glory hole on the left. We were both a little shocked. She continued to stroke me. Looking at the faceless dick and then at me, she said, “Now is your chance.” I swallowed hard. It had been a fantasy, but reality? I was a bit apprehensive. Again she said to me, “I dare you,” and moved my head toward the cock. It was a nice cock, about 6 inches long, fairly smooth and not too much hair. My face was about 5 inches from it. Kay repeated, “I dare you.”

I went for it. I wrapped my hand around it and licked the head. A pearl of pre-cum oozed out. I licked that off. Kay urged me on, “Run your tongue along it.” I did. I came back to the head and swirled my tongue around it. “Suck it!” she said. I let it enter my mouth. I worked a few inches in my mouth. My head bobbed up and down.

At one point I looked over at the Soxer, she was squeezing her tits and playing with her nipples. I love it when she does that. I sucked the dick with more gusto. Suddenly, I felt it swell up. I knew he was going to cum. I pulled off, but not quick enough. The first shot entered my mouth. The rest hit my chin and spread over my hand. I released the deflated dick. It withdrew and I swallowed. The taste was not so bad. Kay looked down at me very pleased, and in fact I was pleased too. We exchanged gazes for a moment.

Suddenly, another cock appeared from the glory hole on the right. This one was big-about 8 inches long. I said to her, “You?” She just shook her head and nudged me toward the pulsating cock. I licked the head, which was dripping with pre-cum. Slowly I sucked the dick into my mouth. It was so big, I had a hard time in getting it in mouth.

Eventually, I was able to move about half of it in. I moved up and down on it. Again, Kay played with her tits. This guy came quickly, and this time it all went into my mouth. I swallowed as much as I could, but some of it dripped out of the corners of my mouth. The cock withdrew.

I sat back up on the bench. We kissed and exchanged cum from the strangers with our tongues. “I want to cum now,” I announced. Kay moved down my body, but I stopped her. I had something different in mind. “I want you to suck me off through the hole.” She looked puzzled. “I’ll go in the booth next door, and you suck me off. But the kicker is that I want you to put on a show so the guy in the other booth can see you through the glory hole. And I want you let me cum in your mouth and all over you tits.” Kay was hesitant. “I dare you.”

She said, “Okay.”

We stood and moved the bench up. I said, “I’ll be in this booth.” I tapped on the left wall, and quickly exited the booth. Just when I was closing the door, a guy entered the booth on the left. I gulped. Now what? The right booth was busy too. I stood there not knowing what to do. After a couple, the right booth opened, and a winded man walked out. I had just sucked him off!! He walked past me and I ran into the booth.

I got situated and looked through the glory hole at Kay. She was sucking the guy in the left booth!! She must have thought it was me! I was concerned but also very, very turned on. True to her word, Kay was putting on a good show. She sucked with her head off to the side. She kneaded her tits. I did not see it very clearly, but I could tell that she was deep-throating him at times. She put on a great show. I was so hard.

Soon, the guy started to cum. He came in her mouth and on her tits. That is when I said through the hole, “Kay what are doing? You’re sucking on the wrong cock!” She immediately let go of the cock and sat back on the bench. The Soxer looked a little dazed. I exited the booth just as the guy in the left booth did. I ran into the left booth. I looked through the hole and saw Kay still sitting there. I heard another door close. She looked down at the right hole and moved her face towards it. She did not realize that I moved. A cock appeared in the hole. I said, “Pssst.” She ignored me, figuring I was a stranger. This cock was a monster-at least 10 inches. She went to town on it.

Again, she gave me a good show. The cum of the previous guy made her tits shinny. Kay did her best to swallow this dick, but it was just too big. I continued to rub my cock. I don’t think I have ever been so excited. Soon the guy came; a huge load spattered all over her face and tits. She looked very satisfied.

I exited my booth and knocked on Kay’s door, “Let me in. It’s CJ.” After a moment of shuffling, she opened the door and I stepped in.

She embraced me and deeply kissed me. She forced her tongue in my mouth. I rubbed her soaked, slippery tits. “That was fun,” she said.

“But Kay, you sucked the wrong cocks.”

“I knew that. I just wanted to put on a show for you!” I was stunned, but still rock-hard.

“Suck me off now.” I sat on the bench and she knelt before me. “You liked sucking those cocks, didn’t you?” I asked.

“Yes. And you loved watching me.” I did. Soon she was deep-throating me. I was close and she knew it. She pulled up and let me shoot on her tongue. She let it pool there. I was spent. Kay crawled up to me and we exchanged my cum.

We both rested for a few minutes. The Soxer put her shirt back on; her chest was soaked so much cum that her white tank top became almost see-though. Her nipples stuck out. We both were a mess-cum all over our faces and necks. “I guess we should get going.”

“Okay.”

We got a few looks from guys as we walked down the hall. The lights in the main room blinded us for a moment. The clerk gave as a smirk and said, “I hope you enjoyed yourself. Come back and see us again soon.”

Kay shocked me by answering, “Oh, we’ll be back soon!”