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May the best man win

"Two boys compete to get a blow job, but they both end up losing"

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Jon and I were friends from high school; we had just graduated in June and were getting ready for college. To get ready for the party scene we had enlisted the help of our former baby sitter, Angela. She was five years older than us and 5'9" tall. She had been a dancer through college and had such beautiful sexy legs and a strong torso. We were from a small town and she had been the sitter for both of us individually and occasionally together too.

She had just graduated with a degree and was enrolling in the graduate program at the same college we were going to attend. As we parked in front of her apartment, we were very excited about the party we were going to tonight.

"Hi Boys, its great to see you," she said as she opened the door to her apartment. She had a huge smile and such beautiful eyes. "Aww look at you, you're all grown up now!" She said as she gave me a hug. I could feel how strong she was as we hugged. I was so horny and girl starved I almost got a hard-on right then. "Oh Jon you look great too!" And she bounced over to him. I could see her sexy legs in the black stretch pants she was wearing. What an ass!

We walked into the apartment and I could smell the perfume and general feminine smell of the room, it was intoxicating. Jon and I had both talked about how much we would love to have sex with her, but she was way out of our league. Smart and beautiful and getting a graduate degree when we were both lucky just to get into a state college.

"So where's the party tonight?" I asked.

"Just two blocks the street. We can walk there now, if you're ready," she said with a seductive smile. I was excited about the party and also the chance to ogle her body all night. And with that, we left for the party.

****

Three hours later, we were slight intoxicated and walking back from the party, Jon, me, and Angela.

"Well boys I think you learned a lot tonight," she said.

"Not as much as I wanted to, that girl with the black shirt totally wanted to hook up with me!" said Jon.

"Right, that's why she left an hour ago with her boyfriend" I replied sarcastically.

"Such a great party anyways," said Jon.

"Well if you played your cards right you could have gotten a blow job out of her, or at least a hand job," said Angela.

"That would be a first for Jon!" I said, and Angela started giggling.

"You mean you've never had a blowjob Jon," said Angela

"No", said Jon, and he looked down at the ground.

"Haha, oh wow, Jon thats okay you're so sweet and innocent," she said.

"Yeah Jon its OK," I said.

"well you've never had one either!" He fired back at me.

Now I looked down at the ground while Angela started giggling even more.

"Well which one of you wants a blow job more?" said Angela, and Jon and I both stopped laughing and looked at her to see if we heard her correctly.

"Well, which one?" She said.

"Definitely me," I said. "No, I want one more," said Jon.

We were at her apartment and walked up the stairs to get inside.

"Hmm", said Angela. "Two young boys at my apartment, both want a blowjob for the first time".

I started getting a hard on as I watched this sexy woman in front of me talk about giving me a blowjob. I was feeling light headed and sat down on the couch. Jon sat down next to me.

"Well, I'm not a slut, am I boys?" She said.

"No," we replied in unison.

"So I'm certainly not giving out two blow jobs tonight. But I'll give out one," she said lazily.

My dick started throbbing in my pants and I could tell Jon was getting turned on as well. God I wanted to feel her lips wrapped around my cock so badly, it would be the greatest thing ever. And I would get a blow job before Jon, one-uping him forever.

"Well lets make this interesting. May the best man win," she said.

"First one to undress wins!" She suddenly blurted out. I leapt up off the couch and so did Jon, furiously ripping off our clothes. My shirt came off, I unbuckled my pants, and stripped off my socks and underwear in record time, but so did Jon.

"Hahahahaha, oh my god, look at you two boys," said Angela. She was sitting in a chair across from the couch, laughing hysterically.

"Ahahahaha, sooo ridiculous. You two are so horny." And we realized we were standing there, naked, in her apartment, with our dicks sticking straight out.

"So gullible. Sit down, naked. Sit back down on the couch," she was laughing, and I noticed she looked at my dick for a few seconds, then over at Jon's, then back at mine.

"Well, I'll tell you both what.

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I'll give one of you a hand job, and one a blow job." she said. "But we're going to do it my way. I want you both sit on the couch, but turn around and face the wall. Sit Indian style, with your legs crossed."

I was so horny, my dick was swollen with blood and I wanted to win this blow job so badly. I didn't even look at Jon but I could tell he was the same way. Naked, we turned around on the couch, sitting and facing the wall. She came up behind us and put a hand on each of our shoulders. Her hands were so warm and sensual.

"Now boys, slowly lean back," she said. I leaned back a little with her hand on my shoulder. "More, lean all the way back," she said. I was balancing precariously on the edge of the sofa, about to slide off.

"Grab the couch with your hands and keep leaning back," she said, kneeling down to be closer to us. She was still fully clothed, I noticed. I held on to the couch and leaned back as far as I could go, my head lower and lower. Finally I felt it hit the carpet. Angela reached out and started rubbing my chest and stomach.

"Ok boys, very good. Keep doing what I say and you'll get your first blowjob tonight," she said.

I leaned back until the back of my head was comfortably resting on the floor. Jon was in the same position. She grabbed my leg closest to her and pulled it back towards my head, curling it towards me. She did the same with Jon, and soon my legs were wrapped over my head and I was staring at my penis, about seven inches from my face.

"Now comes the competition. I'm going to gently stroke you both, and whoever cums first, loses. Whoever is the bigger man, so to speak, and outlasts the other, will win a blow job. And I give damn good blow jobs, "she said.

And just like that, she reached a hand in between both of our legs and wrapped her warm fingers around my dick. The feeling was incredible, I'd never been touched by a woman before, or commanded by a woman before, and she was clothed and older and in control of me. I only hoped that I could last longer than Jon and show her what a man I was. She squeezed my dick and slowly stroked down to the head. My god it felt good! I saw her little fingers slowly massaging it. She extended her thumb to the base of my shaft and gently rubbed between my balls.

"hold on to your loads boys, I want to give you a blowjob. Both of you. But only one can win," she said. She stroked up and down again, slowly, and it felt incredible. I was so excited about the orgasm I completely forgot about the blowjob. But after just five or six strokes I realized that I was already close to orgasm and , looking straight at my penis, realized if I lost I would shoot my load directly onto my face, with my legs wrapped over my head as they were.

She stroked my again, and again, and the feeling grew more intense. I could hear Jon squirming over there and I knew he must be close too. She wasn't stopping for anything, just rhythmically stroking away on my shaft. I only had a few strokes left. Jon was whimpering too, obviously having reached the same conclusion as me.

It felt soo good, and the pleasure spread through my dick and balls, shooting down my legs and enveloping my entire midsection. She wasn't going to stop and Jon hadn't cum yet! With the next stroke I felt my head start to spasm and my balls clenched up, and opened my mouth to scream. "Ahhhh oooooohh mmy goooodddddd" I yelled, and at the same time I heard Jon start to yell too. Another stroke and my dick started shooting cum out, a table spoon at a time, it felt so good. The first load hit my face and snapped me back to reality.

Angela just kept stroking and stroking us both, while we shuddered in orgasm. Every stroke brought another load out and onto my eyes, nose, and even my mouth. It was so warm and smelled strongly.

Angela was giggling uncontrollably. Finally she stopped stroking us and took her hand from my dick to my face. She looked at me and my shocked eyes, and she slowly caressed my face, smearing the cum over my eyes and face, and running her fingers into my mouth. I was in total shock but she held me mesmerized. She did the same to Jon, caressing his face but really just smearing the cum everywhere. It had felt so good.

"Well boys, I guess neither of you is man enough to get a blow job yet. Maybe next time," she said as she stood up.

"I'm going to sleep now. Let yourselves out. See you later!"

My last sight of her through my jizz stained eyes was her beautiful butt, tight and firm and sensual, walking down the hallway away from me. I had been so close. So very close.

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Written by LovingTouch
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