She's the BossbyDreamingofJennifer©
I recently went to visit Jennifer, a friend of mine who was going through a divorce. She's a very attractive blonde whose intelligence and motivation has helped her become a success in the business world. She's the type of woman people look up to and respect, and her strength makes her all the more beautiful.
Of course, her drive to succeed in the work place had hurt her relationship with her husband, so they were now going their separate ways. Although she was going through a rough time in that regard, she told me it didn't stop her from flirting from time to time.
"There are these three guys who flirt with me pretty much nonstop," she said over a glass of wine as we sat and talked in her living room. "I bet I could call all three right now and they'd drop what they were doing if I asked them to come over."
I told her I didn't doubt that. A man would have to be senile not to want to spend a night of passion with her. While her bright blue eyes could take your breath away, her body was just as noticeable. She often complained about her small chest, but I thought her breasts, from what I could tell, were a perfect fit for her thin frame. Of course, like most women, she thought her hips were too big, but I'd be lying if I said I hadn't thought about moving close to her, giving her a kiss, and reaching around to grab her ass and pull her closer.
Maybe it was the business suits and skirts, or maybe it was her success. Or maybe it really was only those deep blue eyes. But for whatever reason, Jennifer was the type of woman who would make heads turn. So when she mentioned there were men falling all over her, I had no problem believing her.
As it turned out, she was feeling frisky and a little tipsy, so she wanted to test her theory.
"You know what, I think you can help me test my theory," she said with a mischievous smile. "I bet those three would do anything to sleep with me."
"So how does that involve me?" I asked, intrigued to say the least.
"Oh, you'll see. Just follow my lead."
With that, she went to the kitchen and made some phone calls.
* * *
Not long after, Jennifer and I were no longer alone in the living room. She had changed into the world's sexiest black business suit with a skirt that showed off plenty of her soft, creamy thighs.
She leaned back in her chair, holding her glass of wine as she spoke to the two men across from her. "I have to admit, you two look great tonight."
Both men had definitely shown up dressed to impress. The taller of the two, Steve, was clearly a high ranking official in some company, and his sharp business suit indicated he was both wealthy and intelligent. The other, Mark, looked to be the rugged adventurer type with square jaw and piercing eyes.
There was a little small talk as we all had a drink, but it was clear neither of them knew what to expect. Neither did I, actually. Only Jennifer knew, and that added a sort of electrified tension to the room.
She crossed her legs, revealing more of her thighs to me from where I stood against the mantel. I immediately wished she hadn't called these two. I'd much rather just be alone with her, even if we were just friends and would never sleep with one another. Can't hurt to fantasize, right?
"Let me cut to the chase, gentlemen," she said in a voice that was both authoritative and seductive. "It's obvious you both would like nothing better than to sleep with me. And to be quite frank, I've fantasized more than once about being with each of you."
I was a little surprised Jennifer was getting the fun started already since only two of the three men had shown up. Didn't that alone prove her theory wrong? But I wasn't about to say anything now. I had no idea what I was in for, but I was interested to see what happened. Plus, I didn't want to ruin whatever she had planned by asking why we weren't waiting for the last member of the party.
The two on the couch were clearly interested in what she was saying. I imagined their hearts racing, knowing that the prize they coveted was almost within reach.
"But while I would love to spend a weekend with both of you doing nothing but exploring your bodies and coming up with creative ways to get each other off, I simply can't decide which of you I want to play with first."
I noticed these two confident men were both squirming in their seats, just a little. She had them right where she wanted them.
"So I brought you both here tonight to see which of you wanted me more," she said, standing now and moving toward them. She knelt down in front of them and rubbed her fingers over their legs. "I have a few plans. A few tests if you will. I want to see just how far you'll go to be with me."
She stood again. "And believe me, boys, no matter what I ask you to do, the reward will be worth it." With each word, she unbuttoned her blouse just a little lower, tempting them with more and more of her tantalizing skin underneath.
She turned to me and said, "James here is my advisor. It seems he doubts my sexuality and my desire. I've asked him here to watch the festivities." With that, she sat back down and motioned me to her so I stood over her shoulder.
"Are you both willing to do what I ask?"
They nodded in unison.
"Good. I first want you to stand and take off your shirts. I want to see if my mental pictures have been accurate."
I looked at Jennifer. She was certainly enjoying herself. The power. The control. Two men in her grasp. She loved it all. And of course, as the two shed their shirts, it was clear she liked what she saw. And why not? Both were in fantastic shape. While Mark, the rugged outdoorsy one, was more muscular with nice tight abs, Steve was no slouch and apparently hit the gym several times a week.
"Mmmm, very nice," she said. "Now the pants."
They both sat to slide off their shoes and socks, then stood again to pull down their pants. Steve was a little embarrassed as he revealed his bright red boxer shorts with little white hearts all over them. Jennifer snickered, but I think she liked them much more than she let on. Mark, however, was wearing grey boxer briefs, and judging by the bulge pushing against the material, he was excited to be here. Of course, Jennifer's soft gasp revealed that she had seen it too and was equally excited.
Jennifer stood and grabbed my hand. She led me over to her boy toys. "You're both doing great. You might say, passing with flying colors," she said, looking at Steve's shorts and winking at him, forcing another blush.
She got on her knees, and tugging at my arm, brought me down with her. From there, she proceeded to gently tug at Steve's boxers until they fell to his ankles. His hard cock stood straight and tall. She ran her thumb along the shaft. "Mmmm, I like what I see."
She turned to Mark and put her fingers under the waistband of his shorts and slowly pulled them down. I watched her smile grow as his cock popped out. Her eyes deceived her for the briefest of moments, the twinkle there telling me she was using all of her strength to hold back from wrapping her lips around his manhood.
"Oh god," she whispered, turning to me with wide eyed anticipation. She reached up and wrapped her hand around each cock. "I was hoping it would be obvious which was nicer, but gentlemen, let me tell you that these are two gorgeous cocks."
She moved her hands over them slowly. "Don't you agree, James?" she asked, turning to me slightly.
"Umm, yeah, I guess," I said, hesitant.
"Oh, come on. Just tell me. Do you have a preference? Who has the nicer cock, Mark or Steve?"
She was toying with me now, and loving every second of it. She was in control and she was going to have her fun.
"They both look great," I said. She winked.
"Here, maybe you need a better view." She stood and motioned me to take her spot. I moved over and knelt inches from two very straight, very large cocks. She leaned over behind me and whispered in my ear. "Which is bigger, James?"
I studied them both, doing what she wanted without question yet without any self doubt either. I didn't even question the fact that I was only inches away from two naked men, their cocks hard and straight. Their size and shape were essentially flawless. Either would have no problem making a name for themselves in adult cinema.
Mark's was slightly longer, easily over seven inches. He had trimmed the area around his shaft and his balls, making his package looking even that much more impressive. Steve's wasn't quite as long, but looked a little thicker. Although he hadn't trimmed his as closely as Mark had, it was still a rather nice, clean display of manliness.
"Maybe it would help if you held them?" Jennifer asked seductively. "Hold them in you hands, James." Her breath was soft and warm on my ear, sending chills down my back all the way down to my crotch, where my own cock started to rise.
With only a moment of hesitation, I moved my hands up and wrapped my fingers around each man's shaft. I didn't need our host to know what was expected of me next, so I slowly began to run my hands up and down each cock. I could feel just the slightest discomfort coming from Mark and Steve, but after running my hands over their warm meat several times, their whole bodies started to move with my hands.
Out of the corner of my eye I saw Jennifer move back to her chair to watch. And I wanted to put on a good show for her, so I focused on my grip and the pacing I set as I jerked off two perfect cocks. Jennifer, meanwhile, had opened her blouse even more and was now running her fingers over her exposed breasts.
Knowing from one of our late night conversations that she enjoyed fantasizing about gay sex, I knew what would get her even more interested in what was taking place in her living room. And although I had never been with a man or even really fantasized about the prospect, I was ready and willing to give her what she wanted. At this point, I'd do anything for her. And she knew it.
With my left hand still moving slowly over Mark's shaft, I moved forward and wrapped my lips around Steve's. I moved my tongue around his bulbous head and flicked the underside of the tip, licking it like an ice cream cone. I pulled back just enough to notice that a small drop of pre-cum had already made its way to the tip of his cock. I looked out of the corner of my eyes at Jennifer and gave her a quick smile, then I extended my tongue and tasted Steve for the first time.
His pre-cum had just a hint of saltiness, but for the most part, it was tasteless. Yet I knew the time for my first real taste of a man would be here soon, so I turned to Mark's cock and gave it a quick lick before I turned back to Steve's and engulfed it with my mouth.
I began to suck Steve's cock, moving my lips up and down on his erection, making sure I ran my mouth all the way to the base before moving back up toward the tip. All the while my tongue slid over the underside of his huge shaft, feeling the veins bulge in my mouth. We quickly found a rhythm, with his hips pumping his cock further and further into my hungry mouth.
I moved off of him, using my tongue to tease the tip. I ran my hand over his shaft, jerking him off while I pleased his sensitive head. He began to moan and I knew he was enjoying my first blowjob. When his moans became quicker and more intense, I took him fully into my mouth again, pursing my lips and sucking deeply as I moved up and down.
I was lost in the movement, enjoying the feeling of his soft yet hard cock running over my lips and tongue. I could feel him getting bigger inside of me, his cock throbbing inside of my mouth. I knew he was nearing the end of his ride, and I took that as my queue to quicken the pace.
Jennifer must have known this to, because she moaned from her chair, "Oh god, James, tease him. Don't let him cum just yet." Out of the corner of my eyes I could see that she had hiked up her skirt and was toying with her moist pussy lips, moving her fingers over herself.
But I was beyond listening, too focused on pleasuring Steve to really care what our host wanted. I might pay for it later, but I wanted his hot cum in my mouth, and I wanted it now.
And I didn't have to wait long. I felt Steve's body tense and his hips gave one final thrust. Then his hot cum shot into my mouth, splashing off the roof with a force greater than I expected. I had to swallow quickly to keep from spitting up any of his hot, salty cum. He shot several loads into my waiting mouth, and I took in every drop.
I pulled back and swallowed again before running my tongue over my teeth and lips to get it all. His cum was creamy, salty, almost bitter. There was a tanginess that I hadn't anticipated. I leaned forward one more time and grabbed his already drooping cock. I slowly pumped him one last time, pulling out one more drop of creamy white cum. I licked it slowly and let it rest on my tongue before swallowing it.
Steve plopped down on the couch, completely spent. I smiled up at him. For the briefest of moments I wondered if I liked the taste of his my first man, his cum. But before I even had time to consider, I turned to Mark and I knew I'd have my fill again. But this time, I'd follow Jennifer's order and tease him some before giving him the relief he wanted.
I moved over in front of Mark's hard cock, appreciating again the nicely trimmed thatch of hair at its base. I leaned in, but instead of moving my mouth toward the tip or to the thick shaft, I turned my head so I could run my tongue over his smooth balls. I opened wide and gently placed one then the other in my mouth, running my tongue over each one in turn.
I then moved up along the underside of his shaft, which was already throbbing. It stood tall and thick as I traced the tip of my tongue along the vein that led from the base all the way to the round tip. Once there, I wrapped my lips around his head and ran my tongue over it, toying with his tiny slit.
As my mouth began its journey up and down his manhood, I moved my hands to his muscular thighs. I ran my hand over them, caressing the insides up near his crotch and then down again. Once his hips started to move with the rhythm of my sucking, I moved my hands up to his ass, gripping each muscled cheek and pulling him tighter toward me, which allowed me to take him in deeper and deeper into my mouth before pulling out ever so slowly.
I wanted nothing more than to suck on him and make him cum right then and there, but I resisted. I wanted to tease him first, so I pulled off of him and moved my lips to kiss around the base of his cock, blowing gently on his lower abs and crotch while keeping my hand moving up and down on him to keep him nice and hard.
I moved back to his erection, which bolted upright at the attention it received from my tongue. I kissed the tip, then licked it slowly before wrapping my lips around him and taking him fully into my mouth. When Mark grabbed my head and pulled me toward him, I knew he wouldn't let me tease him anymore. He wanted to cum as much as I wanted to make him. So I gently pushed him back to the couch where he sat down. Bent over his lap, and with his hands still guiding my head, I went to town on his huge, thick cock, sucking him with a sexual frenzy I had never experienced.
I lathered him up good with my mouth, moving faster and faster over his hard cock. My hands covered his body, running over his stomach, chest, and thighs. When his cock started to throb, I knew he was close to exploding in my mouth, so I doubled my efforts, rubbing him with my hand while I sucked him with everything I was worth.
When he burst into my mouth, I swallowed quickly and often. It was a big load, but I managed to take it all in. I savored it on my tongue, loving my second taste of man. As with Steve, I rubbed the last drop out of his cock and licked it off with my tongue, already regretting that the experience was over. When I looked up and saw his exhausted look, I knew it didn't have to be my last.
With both men spent, I turned to Jennifer. She was working feverishly on her clit, her fingers glistening with her own wetness. She slowed down as she realized the show was over, as if coming back from a daydream. But the way she looked at me told me this was just the end of act one.
She stood and pushed down her skirt, leaving her blouse unbuttoned. She moved toward me and reached for my hand. As I stood, she kissed me so deeply I wished for that fleeting moment that I could stay in that embrace forever. Instead, she broke off that powerful kiss and said, "Gentlemen, I've made my decision." She looked at me. Her eyes told me exactly what she wanted. And she wanted it now.
With that, she moved off, leading me toward the bedroom. Looking back at the two on the couch, I suddenly realized I had been wrong earlier. There were three men involved with Jennifer's little experiment. And somehow, I was the one going home with the prize.
When she shut the bedroom door and fell against it in anticipation, looking at me with hunger in her eyes, I knew it would be a prize worth any test she could've possibly given.