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A Past High School Flame

We arrived at the Reef, it was Wednesday and you were looking forward to $6 wines a maybe splitting a simple wrap. Malissa must have read your mind as she reached for a new cold bottle. As she poured, you shared your cancer diagnosis and treatment. Malissa was of course supportive and took it as the reason why we had not seen her in a while. You then asked Malissa, pour a “Fireball” for Al, I need to warm him up a bit. Fireball? I thought to myself? The drink had been a code word Dave Green. I downed the shot and you motioned to Malissa to pour me another. OK I thought, as I downed the second, already feeling the warm of the first. “Give us a few minutes Malissa and he will be ready for another…

You had a naughty smile on your face as you sipped your wine. Knowing it would not take long for those two shots to have the desired effect. You could see my posture soften as you pushed my glass of wine towards me. As I raised the glass to take a sip, you commented. “ I shaved last night”.. Letting the words linger for a few seconds. Dave I asked? No.. Actually, a better “Fit” for both of us. The bar was getting busier as Malissa asked if we were ready to order. “Just another shot for Al”… By the third shot you could tell, it was time to share.

So, you started. “A month ago, or so, I received a friends request on Facebook from an old high school boyfriend. His name is Jim, but with a knowing smile on your face, I called him “Tip”. So, tell me more. We were both seniors, he was smart, treasure of our class and on the basketball team. Which is why I was able to call him “Tip” even though it really had nothing to do with this basketball skills. We have been messaging back and forth and kind of reconnected. He’s divorced, no kids, lawyer, new to Syracuse after moving back from North Carolina. I know I should have cleared this with you, but I expect him to stop by in a few minutes. The three shots had clearly taken your intended effect, as I said, well I think I know where this is going.

It was not hard to miss him when he came in, tall, well dressed, confident. Malissa as well as most of the bar fly’s noticed as well. He did a direct bee line to you. You stood, giving him a more than friendly embracing and very lingering kiss. He then took his time, holding the bar chair for you, making sure you were tucked in and comfortable, before he turned to me. He was a few inches taller but had at least fifty to seventy pounds on me and he made it clear from his handshake that he was the Alpha here and I let my hand relax to acknowledge the same.

Then with a very fluid but deliberate move, he took my seat. Immediately he engaging you with conversation as I sat on another unbacked cold metal bar stool. By this point, Malissa was all over him, smiling. Jim did a quick glance at the top shelf bar stock. With a slight hint of disappointment at the selection said, “Double Southern Comfort, neat, short glass”. I watched as Malissa did a generous pour for Jim and did the same for me but with Fireball. She delivered the Southern Comfort and slid over my wine and double Fireball. Under her breath whispering; “The Fireball’s on her. I think you will be needing it.”

I understood, as for the next twenty minutes you and Jim basically did everything but rip each other’s cloths off. Conversation, laughter, your light touches of his shoulders. Jim a bit bolder, running his hand up the inside of your jean cover pussy before bringing his fingers to his nose to smell your scent. Finally, knowing that I must be feeling a bit left out you turned to me, asked if I was ok? …. From behind you, Jim kind of stared me down, “Maybe you should invite Jim back home is all I could and knew I was expected to say.

Fifteen minutes later, Jim was striding throughout our first floor, even thought I was clearly buzzed, I could tell his was impressed with his surrounds. He wasted no time with small talk or another drink. Taking you by the hand he guided you up the stairs. I knew you were comfortable, safe with him, so I hung back, I understood the importance of you having private time with a past boyfriend.

I took a Fireball from the freezer, taking my time downing it before heading quietly up the stairs. Peaking in, Jim was standing naked at the end of our marital bed, you sitting on the bench. I then understood why you called him “Tip”. While he was clearly above average in size in length and girth, the head of his cock, the “Tip” was a freakishly large mushroom shaped head.

I watched, memorized, as you lovely, kissed the “Tip” of his harding manhood. I understood it had been at least fifty years since you had fondled it last. My guess it was now, even larger than it was back in high school. I was sure you had given him “Head” before, probably many times. There was a bit of doubt in my mind if he has ever been able to do more than just rub the “Tip” of the monster over the outside of your tight high school pussy. It was clear, tonight he was going to finally going to get more than the “Tip” of his cock deep in your now married pussy. Finally delivering a huge load of his warm potent sperm deep into your womb like he so wanted to so many years ago. By now you both were clearly enjoying each other. You licking, kissing, partially mouthing his cock. You knew you could not actually give him deep oral; the head of his cock was just too large. Soon you were standing, your jeans dropping to the floor. He smiled approvingly when saw your smoothly shaved womanhood. For him however, all he saw was that tight high school pussy that he was finally going to properly “Break-in”.

Jim had been here many times before with married woman. He had learned that no matter willing, wet a woman was, she would need some additional lubrication for penetration. Looking at me, he said “Lube” ? It was the first time he even acknowledged my presence. As I found and handed him the Astro-lube, he gestured for me to be quite and just watch. He then pushed the bench out of the way, gently guiding you back onto our marital bed. He lubed his cock generously and ran the bulbus mushroom “Tip” of his cock up and down your pussy lips, teasing you. Warming you and him up for the main event. Then for the next few minutes he gently pressed the “Tip” of his cock into your married pussy, ever so slowly. He took his time, letting your pussy naturally yield to his size. He lovely asked several times if you were ok? He understood his size. That his cock could bring great pleasure, but it could also bring great discomfort. There was no doubt from your encouraging moans, Jim was doing it right. With each stroke he penetrated a little deeper before bottoming out eliciting a satisfied moan from both of you … and me. Once he achieved full penetration, he kept his genitals tightly locked to you for what seamed like forever. Wanting to remember this moment. He had finally gotten to “Nail” that gal he so lusted over when he was 17..

I then watched as Jim began to fuck.. mate.. with you. In and out.. In and out.. over and over. You both were experiencing something special, I know you have faked orgasms so many times, but not this time. For the next thirty minutes I submissively watched as you experienced multiple orgasms. Witnessing the clenching of your pussy around Jim’s cock, bringing him closer to his release each time, but he had amazing control. Then I watched as your body just began relaxing, slipped slowly limp. The combination of wine, multiple orgasms was sending you into a deep satisfied sleep. Jim understood, it had happened before with woman he fucked. It was now his time. He pounded away at your pussy for several more minutes before giving one last hard deep satisfying thrust. I watched as his large testicles contracted and his cock begin to rhythmically pulse .. five.. six.. seven.. times releasing a torrent of his warm potent sperm deep into your receptive married womb. Jim then kept his genitals tightly locked to yours. Wanting to assure all of his load stayed deep inside you as he initiated on another post coitus kiss. But he found you all but non-responsive. You were clearly done for the evening.

I figured he was done, but no. Sitting back on the bench, he waved me over, telling me to strip. He smiled approvingly, finding me in a pink pair of lacy sissy panties. “Al .. We are going to get along so well…”. He pulled the satin pouch to the side a bit, liking that my clitty was small, contracted, limp. He directed me to turn, to show him my ass. “Your shaved, smooth, nice, he then roughly pressed a finger deep past my rosebud. “Your so tight, I just might have to “Tap” that, but first, clean my cock..” I knelt in front of the bench, as he dangled his semi-flaccid cock in front of me. It was becoming clear, but unexpected, he had a dominate bisexual side. Then with slow licks I began cleaning him, servicing him. Soon he began to press the back of my head down wanting me to take all of his enlarging gland deep down my throat. Holding me there till I started to gag to reinforce his dominance. The combination of your scent mixed with his male musk was overpowering… intoxicating… Jim could tell as I took his cock deeper his manhood continuing to engorge, I was ready to his good little gurl. .. Soon his cock was too large for even me to pleasure properly and I move to licking his hair covered balls..

That’s nice he said.. But I want to see you clean up my load. You were still deep asleep as my tongue found his sperm pooling at your open flower. I lapped, enjoying, finally, being allowed to be involved. I loved the feeling of submissiveness. It was apparent, I was there to be a good understand, supportive cuckold. There to just provide oral services. I was still enjoying licking his load as I felt his large warm hands kneading my ass and a cold stream of Astro lube running down it. Jim then pressed his first finger inside me. He found me receptive to his touch as he worked a second and then third finger inside me. By now he could tell I was going to be totally submissive to any of his needs. He guided me to the far side of the bed, having me lay on my stomach. He aggressively kicked my feet apart. Face down, I felt a strong hand in the center of my back, securing me in place as he ran his cock slowly up and down the crack of my ass a few times. He took his time, enjoying his dominance and what he was about to enjoy doing. Soon I began to feel the pressure of his mushroom head, just the “Tip. Quickly finding the entrance to my boi pussy. “Just relax.. Kay says you been bred a few times.. But I can assure you I’m going to spoil you with an experience you will never forget..” I had just the right number if Fireballs, as I did my best to accept what was about to happen, but I still winced with a bit a pain as my anal cherry was finally properly popped by a well hung dominate male. Jim was not as gentle with me has he had been with you. While he was generous with the lube, he was not there for my pleasure. I was there for his. I laid limp under him as he pounded away for several minutes. I could feel his impending orgasm building when I felt the warm touch of your hand on my back.. Your fingers were interlacing with Jim’s... Looking over, you were awake, smiling, supportive with soft whispers that Jim is good for both of us. Jim then changed his position, his full weight now on top of me, he was in full control now as his thrusting became more urgent. Jim could tell I was beginning to tremble with an impending prostate orgasm, and it was exactly what he was waiting for. With one more thrust he released his load deep in my boi pussy knowing I was at the same moment releasing my warm gurl clitty milk into my sissy panties.

I then felt him relax, his full weight still on top of me, wanting us both to enjoy the afterglow of our mutual orgasms. I could feel his cock softening as I felt his release dribble from my boi pussy and down the crack of my ass. When he finally rolled off me he had a satisfied, contented smile. He had finally found a true hotwife/cuckold couple. Even better, one with a submissive, maybe even slightly feminine bi hubby that would be lots of fun to train. After this evening experience he was going to make sure this became a long-term thing. What was wonderful, we were both knew we had found the perfect play partner as well. Both of us looking forward to his next visit.

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