Wendy Wins Our Bet

Sex Toy
2006-03-12

“How about this,” I said with a smile. “If State wins, you have to do what I want in the bedroom, and if Tech should somehow get lucky and win, I have to do what you want. ”“That sounds good to me,” Wendy replied. “But let me guess: If your team wins, I will be dressing up in those new schoolgirl shirt, skirt and stockings you bought me, and I will have to talk to you about my bad grade. Of course, I am sure my teacher will give me a spanking and I will have to suck him off as well. ”“Oh yeah, that sounds about right. But don‘t forget the teacher loves anal action too,” I said as I laughed. Wendy knows the teacher-student scenario is one of my favorite role plays, and that I will ask (or beg) for it quite often. “So what if you win the bet? What will be in store for me?”Wendy cracked a smile when I asked the question, and added: “Oh, I‘ll think of something. ”I wasn’t sure what to make of her answer, but I didn’t think much of it as we settled in to watch the game. We snuggled together on the couch, munching on some popcorn as we watched what turned out to be a close game. I love having Wendy near me; I could hold her in my arms for hours. Two hours later, Tech came out with the win, and Wendy was wearing a big smile. “I guess I win,” she said with a grin. “Yeah, I guess so. So what exactly do you win?” I said.

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  “Well … you’ll find out after dinner tonight,” she said with a twinkle in her eyes. “O. K. … I guess that sounds all right,” I replied, with a little dose of excitement evident in my voice. Later that night, after we enjoyed dinner, Wendy went upstairs to our bedroom while I cleaned up and did the dishes. She told me to come upstairs when I was done. Thirty minutes later, after I had cleaned up, I bounced up the stairs with wild thoughts running through my head. Wendy seemed to be planning something new for me, but what could it be? I stopped at our bedroom door to compose myself, and then I opened the door to see something I never would have expected. Wendy stood in the center of our room with nothing on … except a big smile and a strap-on dildo. To say the least, I was shocked and I am sure I had a dumbfounded look on my face. I had no idea she owned a strap-on, let alone wanted to use it on me. “Come on in baby,” Wendy said with a smile. “I hope you are ready for something new. ”“Well … maybe,” I answered, as I stared right at her pink dildo that she was wearing proudly. It looked about 6 or 7 inches long, and pretty thin.

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  “Well Ted, you lost our bet. And I decided that for losing, your teacher wants to be sucked off, and wants some anal action. Now strip for me,” Wendy ordered, with a serious tone in her voice and a smile on her face. I did as I was told, stripping naked in record time. Wendy seemed to like the fact I was ready to play by her rules. “Good boy. Now get down on your knees,” she ordered, and as I dropped to my knees she approached me. “Let’s get started. First, I want you to give me a blow job. ”I have never done anything like this, and I’m sure my trepidation showed on my face. Wendy noticed, and in a soft voice said: “It’s O. K. , Ted, we can go slow if you want and we can stop anytime you want. ”I looked up at Wendy and smiled. “No, I am all right.

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   I am ready. ”With that, I lowered my mouth on her dildo. I started my licking the head, starting with the smallest of contacts with her new toy. But I quickly tasted her juices.

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She obviously had used the dildo on herself while waiting for me to finish cleaning after dinner. The taste of her pussy juices drove me crazy, and I started to take more of the dildo in my mouth. Like I said before, I had never done this before … but at that moment, I was really enjoying myself. “Oh yeah, that is nice,” Wendy moaned as she ran her hands through my hair. She lifted a leg over my shoulder, and took one hand behind my head to pull my face in tight to her body. I responded by taking the full dildo into my mouth for the first time. I was caught off guard, and nearly gagged a little, but I quickly adjusted to the situation. As I started to bob my head up and down her, I realized I liked having the thing all the way in my mouth … because that put my nose right in position to take in the sweet aroma of her pussy. “Oooh, I like that baby,” Wendy cooed as I worked her dildo in and out of my mouth, stopping each time at the base to enjoy her aroma. I slid a finger near her pussy, and I could tell she was soaking wet. That upped my excitement even more.

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   I continued to suck on her dildo, quickly developing a nice rhythm, running my tongue all over her plastic fuck stick while using my hands to play with her ass. I ran a finger into her asshole, causing her to moan loudly. A few minutes later, I ran two fingers into her asshole, and shortly thereafter, I buried three fingers into her sweet hole. “Oh Teddy, I like that … but now it is time for me to play with your ass,” Wendy said as she pulled away from me. She pulled some lubricant out from a table and tossed it to me. “Why don’t you do the honors?”I did as I was told, squeezing a fair amount of the lubricant into my hand. From my kneeling position, I turned my attention back to her dildo. I ran my lubricant-covered hand up and down her dildo, covering every square inch of the toy with my strokes. At the same time, I used my other hand to reach up and grab her left breast. She has small areolas with perky nippes that simply command attention. I ran one of her rock-hard nipples through my fingers, causing her to moan when I tweaked it between my thumb and forefinger. “O. K. , I think we’re ready,” I said as I stroked her dildo one last time. With that, I climbed onto the bed where she had placed a pair of pillows for me to prop up my ass.

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  “We’re not quite ready,” Wendy answered as she took the lubricant bottle and squeezed some right into my ass crack. As the lubricant rolled down to my asshole, Wendy ran two fingers into my hole and proceeded to spread the lubricant as much as possible. “Wow, that is nice,” I muttered as Wendy worked her fingers in and out. She has run a finger or two into my asshole in the past, and it always felt good, but for some reason this time felt especially good. My cock was starting to grow harder. Wendy continued to work my asshole for two or three minutes, and also reached down to give my balls some attention. Then, she stopped and said: “O. K. , are you ready?”“Yeah, I think so,” I said in an eager tone that surprised me somewhat. Wendy took the cue and started to work her dildo into my asshole. Needless to say, this was a tight fit, but she quickly popped the head into my hole. I gasped a little, causing Wendy to giggle. She clearly was enjoying our role reversal. She stopped for a minute to let my body adjust to this new experience. Wendy slowly worked her dildo into me with short, slow strokes.

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  “Oh, I’m not sure about this,” I said. The dildo was pretty thin, but it felt awfully thick to me at that moment.

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“C’mon, you’re OK,” Wendy replied as she started to pick up her pace, at the same time running a hand over the small of my back to comfort me. Then, she grabbed my hips tightly and started working her dildo quicker, and I felt her slam me with a hard stroke. “Aww, ooh, is that all the way?” I asked, prompting Wendy to laugh. “No, that is only about halfway baby!” she said. “But speaking of all the way …”With that, Wendy buried it all the way into my asshole for the first time. She left it all the way in for about 20 or 30 seconds to let me adjust. "How does my baby like that?" she asked. “Ummm … oh yeah … ummm … I like that a lot!” I said as I felt the dildo expand my tight hole. With that, Wendy went for broke. She started slamming in and out of my asshole with quick, precise strokes. “Oh yeah, Wendy, fuck me hard baby!” I moaned, at the same time lifting my ass to meet her strokes. Much to my surprise, I was enjoying this a lot. Wendy giggled as she started rocking my asshole with long, hard strokes.

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   I could not believe how good it felt to have my girlfriend fuck me like this. I could feel my dick becoming harder and harder with each stroke. “Oh baby, your ass is so nice. I could fuck you all night long,” Wendy said as she smacked me on the ass, causing my dick to grow even harder. “Oh, oh, oh, yeah,” I muttered as Wendy stopped for a brief stretch to lean down and kiss my neck. She quickly resumed her hard strokes, which were giving me the most incredible feeling. Finally, with my dick ready to burst, Wendy pulled the dildo out of my ass. I’m not sure what she was planning, but I pounced on the opportunity to flip her over onto her back. I quickly pulled off her strap-on, and dropped my nose into her beautiful red pussy hair that I love. I quickly ran my tongue along her slit, which was soaking at this point. I darted my tongue in and out a few times, and nibbled on her clit just enough to elicit a long moan. “Fuck me baby … fuck me hard … fuck me now!” she yelled, but I continued to suck on her clit. Knowing I love it when she yells, Wendy let out a scream: “Fuck me Ted … fuck me please!”With that order, I ran my 7-inch dick up and down her slit, coating my dick with her juices. Wasting no time, I quickly popped my head into her, causing her to gasp just a little. Wasting no time, I proceeded to slam my rock-hard cock to the hilt.

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   My cock had never felt so hard in my life, and her pussy had never felt so warm and inviting. Her pussy seemed to grab my cock like never before. I pounded Wendy with hard, fast strokes, bringing moans from her as I hit all her favorite spots. She ran her fingernails deep into my back, tearing at my skin . . . something she knows I love. I responded with my hardest strokes. "Mmmm, oooh, damn baby!!" Wendy yelled as I brought her legs up to my shoulders, and grabbed her ankles as I pumped my dick in and out. She loves this position, and I quickly brought her to an orgasm that rocked her body for what seemed like a couple minutes. I followed close behind, unleashing a large load deep into her pussy. Later, after we recovered, I fucked Wendy in the ass and brought her to another orgasm. After pumping my load into her ass, we fell into each other's arms and giggled. We obviously had just started a new chapter in our sex life, and we could not have been happier. .

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