A Orgasmic Prom Date with my Best Friends Son in Watford

Rushing around the house, we were making sure everything was locked and we had all the things we needed for the weekend. We were making one of our occasional visits to Watford. The trip usually took just under two hours, but it felt as if we were going across the country. Carol and I had been best friends since first grade and until recently we always lived within walking distance of each other. They moved because of an excellent job opportunity working as a personal assistant in Watford. I missed having my friend around, but since we were still relatively close to each other, we visited quite a bit. Also, it's a good excuse to take more mini vacations together.

Their son, Ian and mine Lee had been the best of friends growing up. They still were close, but know with the distance they hadn't really kept in touch. My daughter was a little older, so they really didn't hang out too much. It's still hard to believe Ian is eighteen and a senior and that my kids are in their twenties and in college.

In an old life I had been a math teacher at the high school before our kids were born. When they reached school age I stopped teaching and took up real estate on a part time basis in order to be home when they were. Finding that I preferred it to teaching, I decided to stay, and have done quite well. With my husband, Mike's job as a programmer I was able to stay part time even after the kids were pretty well grown.

In school, Ian had quite a bit of trouble with math and he would come to our house after school so I could watch him until Carol and Martin got home. Since I loved math and missed teaching, I took the opportunity to become Ian's tutor. It's funny, he obviously knew the subject, but still insisted that I show him every step several times before he had the confidence to do it himself. It's like if I wasn't hovering or leaning over him, he couldn't do anything.

They moved right before Ian started High School and now he is in advanced classes so I feel I was able to rub off on him. We had always got on well even though I hadn't really seen much of him since he started they moved.

The last time I saw Ian, was at a swim meet last year. He had always been big, but now not only did he have a swimmer's physique, but he towered over me and Carol. But I still see the little kid who'd complain that, "It's too hard."

Mike watching me run around checking locks and making sure we had everything, for some reason always arouses him; walking up behind me, he grabbed my breasts and nuzzled his mouth on my neck. Knowing I needed to do something if we actually want to make the trip, I spun around, dropped on my knees and opened his fly. Grabbing hold I ran my tongue up and down the shaft, then circled his head. With the foreplay done, I swallowed his member while I massaged his balls. After twenty-five years of marriage, I've learned what it takes to satisfy him and to and give him what he need so that we can do whatever we needed to. And he does the same for me. Hearing his breathing begin to speed up, I knew he was getting ready, and when his body stiffened, I pulled my mouth of him, maneuvered so I wasn't facing his throbbing cock and jerked him to completion. Seeing the mess, I almost regretted that I didn't swallow, but the thought frankly is unappealing in the extreme.

When we were younger, he'd occasionally ask me to let him come in my mouth, but each time I tried, I couldn't bring myself to do it. Now, he doesn't even ask which, frankly, I'm pleased with.

We finally arrived on Watford at Carol and Martin's house just after noon. They had a nice lunch waiting for us and we sat down and caught up with what we were up to. After finishing and cleaning up the dishes, Ian came in and joined us. We talked about school, his grades and who he was planning on going to the prom with.

"I don't think I wanna go."

"What?" I said not believing what I heard. I mean, he was six feet two, chiseled with curly dark hair and deep blue eyes. How could he not go?

"Yeah, I'm not really much of a dancer and there's no one I really want to go with, besides, It's a hundred dollars a couple or fifty a person."

"Hey!" I said, "lock us both up in a room and I'll have you dancing . and then some."

Laughing, Ian was about to say something when Mike piped in, "Now you've done it. I think you're going now, even if you have to take Diedre."

As Mike was speaking, I grabbed my purse, pulled out a hundred dollars and handed it to Ian. "Ok, we're going, now when you do get a date, just use the money for a nice corsage."

I spent a good part of the weekend showing Ian how to dance, from fast freestyle to ballroom. He picked most of it up so fast, it was hard to believe he was so worried about it. I felt like I was his personal tutor again and that he was a sponge into which I was pouring my knowledge. I really enjoyed the weekend and was almost hoping I'd end up being his date, since Mike and I didn't really get out to dance too often any more. During the weekend, Carol pulled me aside and said, "Thanks for showing Ian how to dance. I swear, I don't know why he doesn't want to go to his prom. It's not like he doesn't have a date every weekend and he's constantly surrounded by girls."

"Well," I answered, "some people just aren't into that kind of stuff, the formal wear and all the other trappings."

"Yeah. But I am glad you convinced him to go and that you agreed to go with him if he doesn't want to go with anyone else."

"I do feel a little weird about it, but if I do end up going, I'll make sure he dances with so many girls, he'll forget I'm there."

"Thanks, I'll owe you a big one for this."

Of course, as the date approached I was becoming more concerned that I'd actually have to go through with the prom thing. Here I was, a forty-three year old possibly going to a high school prom with an eighteen year old. Two weeks until the prom, I had spoken with Carol and it looked like I was it. Wondering how such a hot young man could not have lined up one date completely baffled me. But since I did promise, I went out and bought a knock out prom dress. I also got some hair color to get rid of the little grey I had in my hair.

After talking with Mike, then Carol, I decided the best option was for me to get a hotel room near Watford where the prom was being held. That way, if anyone had too much to drink, they'd have a place to crash. Also, I didn't think I'd want to drive back to Carol and Martin's place after, much less home, so I'd crash nearby and drive home the next day.

The day of the prom eventually arrived and I was still the one Ian was taking. It's like he didn't even try to find someone else. I wanted to check into my hotel and have Ian meet me there before going to the prom. Unfortunately, Carol and Martin were getting too into the idea and insisted I go to their place to pose for pictures and pretend everything was normal. I admit, I enjoyed the attention and felt like a teenager again. I got into my nice but simple black strapless dress, fixed my hair and got myself ready. I looked at myself in the mirror and thought, "Damn, you look good." I can't pass as a high schooler, but I think I look darn good with my dark shoulder length hair, green eyes and my hourglass figure.

As the flashes went off before my eyes, I felt more at ease with Ian having his arm around me and holding me while we posed for the an endless number of pictures. Carol and Martin were enjoying the spectacle, but not nearly as much as I was. I know it was Ian's prom, but as far as I was concerned I was the center of attention and I loved it.

After posing for the official photographer, we wandered around the hall looking at the beautiful decorations and settings. Finding our table, we hung out nearby and engaged in small talk. Many of the boys as soon as they noticed us were stepping over each other to meet me and all were very nice. The girls? Well they pretty much ignored me, which really didn't bother me since I wasn't there for them anyway.

We sat down and ate, chatted and enjoyed listening to the music in the background. When the dessert was finally finished and the dance floor was officially opened, Ian grabbed my hand at the first note as if racing to be the first ones. We didn't quite make it, but it was a photo finish. The first couple of songs were fast ones, but the third was slow. Ian held me close to him and I got lost in his strong arms.

He was so smooth and graceful I had a hard time believing he was nervous about going dancing. Something seemed oddly familiar but I couldn't quite put my finger on it, I also noticed that I was becoming aroused. When the song ended, he wanted to stay, but I suggested we go back to the table and take a break, and maybe he could dance with some other girls. He didn't seem interested and I didn't want to force him to do something he didn't. In the end, he did dance with a couple of other girls probably because several of the boys had asked me to dance.

Near the end of the night, Ian and I were pretty much glued to each other on the floor. During another slow song, I realized what seemed familiar. I asked Ian what cologne he was wearing. He told me and I remarked, "That's what Mike wears, mmm I love it."

"Really?" Ian replied nonchalantly.

Thinking about Mike really got my juices flowing. I now regretted the decision to spend the night and really wanted just to drive home and jump him before the door closes.

Suddenly, as if splashed with cold water, I remember part of why I was here. Unfortunately, I was monopolizing Ian and not letting him mingle and dance with the plethora of young women in attendance. Here I was, an old woman reliving my youth and denying Ian his.

Feeling my cheeks flush, I told Ian, "I need to go out and get some air."

"'K, I'll come with ya'."

"No, stay here and have fun, I won't be long."

"Na', I could use some air too, but if you want to stay, I'll come back in a few minutes."

"Deal," I replied.

From the stuffy ballroom, the little breeze from outside felt nice. Unfortunately, being out here on a nice night with a beautiful, clear sky above, I started to feel even more aroused. Ian looked at me concerned, "Your face is getting red, you ok?"

"Sure, just needed some fresh air," I replied.

Walking to the edge of the patio, the slight breeze felt really nice. Noticing several other people spread out on the balcony, talking or holding each other swaying to the beat that wafted out from the main floor. Taking a deep breath I looked out onto the busy highway and streets below. Sensing someone right behind me, I looked and saw Ian gazing up at the sky. Hoping this would quell my rising hormones, I found that it actually intensified them.

"Beautiful night," he said.

"Yes," I answered.

"An almost perfect evening."

Turning to face him, "Almost?"

"Yup."

"Then go back in and make it perfect!" I sternly said.

"Oh, I plan to."

Waiting for him to go, I looked up and saw he was just looking at me, almost through me. Glancing at my watch, I saw that it was nearing midnight. Putting some firmness into my voice, I said, "I really can't keep up with you all; go back in, I think I'll head to my room."

"Just one more dance?" he inquired smiling.

"Look, you're wasting this night, go in and give some girl a nice memory, I'm don't think I can last much longer."

"Ok . you win, just let me walk you to your room and I will say goodnight." Thinking I had finally got him to listen, I agreed. I would make sure to send him back down so I could have some alone time.

Arriving to the room, I opened the door and was surprised when he walked right past me into the room. Looking at him questioningly I said trying not to sound exasperated, "You really should go back; you don't have much time."

"Oh, I think I have plenty of time," he said looking into my eyes as he put his hand on my shoulder and gently began running it up and down.

For a long moment I remained frozen, unable to do or say anything. It was only when I was able to turn my face from him that I was able to think again. Backing away from him, he moved closer and put his free hand on my other shoulder repeating the movements with more firmness. Looking into his eyes again I was transfixed, feeling the tingling between my legs virtually erupt. Slowly, he leaned in towards me and it was all I could do to again try to pull away. "No!" I said, "You can't."

Turning away from him and facing the window, he walked up and put his arms back on my shoulders. Despite my protests, his touch caused a bolt to run through my entire body.

"You're shivering? You cold?" he asked.

Unable to tell him that the shiver had nothing to do with the temperature, all I could do was shake my head. He then nuzzled my neck, lightly flicking his tongue up and down.

He stopped at my ear and whispered: "I've been waiting for this moment forever."

Hoping to deflect him, I pulled away and turned toward him, "You're crazy, I'm old enough to be your mother, hell, I'm your mother's best friend."

"I mean it," he said. "I've wanted you for so long. You are the most wonderful woman I've ever met."

Blushing I stood there stunned not believing what I was hearing. Taking my lack of anything as a sign, Ian moved toward me again. I surprised myself by remaining where I was as if unable to move. His face came within inches of mine. He wetted his lips, took a breath and kissed me.

Not only did I not resist him, I responded by kissing him back. All the pent up energy that I had been fighting all day suddenly surged through me. I loved feeling his strong hands caressing my back, running down and roughly massaging my butt cheeks.

After what felt like an eternity, I was able to push him away. Feeling weak, I sat down on the bed dazed and confused. Ian sat next to me, looking into my eyes, he bent his head forward and kissed me again. This time, though, he moved his hands to my back and slowly pulled down the zipper. I sat there returning the kiss, then moved my arms so the dress fell to my waist.

Feeling his hands reach around searching for the clasps to my bra, he quickly found it and attempted to release it. Pulling back a little I said, "No!"

Ian just looked in my eyes and was able to unhook the bra then let it join the top of my dress on my lap. "No!" I said again but remained sitting where I was . My eyes were staring into his. Mesmerized, I remained still as his hands moved down to my hips.

Without any conviction, I said, "No!" once again. As if he wasn't aware that I had said anything, he laid me back on the bed and pulled my dress down the rest of my body, over my shoes then tossed it aside. My panties soon joined them as I lifted my bottom to help him remove them. Now that I was naked on the bed, Ian picked up the pace, practically tearing off his clothes. He was soon on top of me, massaging my breasts and kissing me as if he only had a minute to get a lifetime of kissing in. I felt his stiff penis on my stomach as he reached with one of his hands between my legs.

Feeling how wet I was, he began kissing and licking down the length of my body. Squeezing and tugging my breasts while sucking each nipple, I had to tell him to ease up, they weren't going anywhere. He then went down waiting pussy and slowly began circling the edges of my labia licking and lightly nibbling the skin. After driving me crazy for a good while, I grabbed his head and pulled him closer into me. Taking the hint, he began fucking me with his tongue. It didn't take long for me to have another sweeping orgasm that left my body quivering and gasping for breath. He continued tongue fucking me as he deftly added his fingers to the mix. He easily got four fingers into me as his thumb rubbed against my clit. This sent another intense orgasm pulsing through my worn body and satisfied body.

Lifting his head, he made the trek back up my body, kissing and licking until he was positioned between my legs.

He grabbed his ready member and rubbed the head up and down my pussy lips, torturing me.

"Fuck me!" I cried and he pushed himself into me. I couldn't resist a second longer and experienced the most thunderous orgasm of my life. Screaming as he continued to pound into me, I never wanted the feeling to end. Unfortunately, the feeling did begin to recede. As I somewhat regained some sense of clarity, I asked "Wait! Do you have a condom?"

As he continued pushing himself into me, I said, "Don't cum!"

With urgency in his voice, he replied, "Let me cum in your mouth!"

"No!" I said.

Not listening, he pulled out, leapt up to my face in a fluid motion, grabbed my head and inserted himself into my open mouth. Immediately tensing up, Ian shot his semen to the back of my throat. Trying not to choke and with his cock still in my mouth, all I could do was swallow the load. After several more squirts joined the first in a run to my stomach, he leaned back on the bed as I rolled over with his cock still in my mouth, still pumping him as the heat slowly dissipated from his member. Feeling a little queasy after swallowing his gunk, it turned out to be not as horrible as I expected. Still, it's not something I plan to make a habit of, but...

Pushing off of him and lying beside him, he said, "Sorry," rather half heartedly, "but you've definitely given me a great memory."

Sighing, I replied, "You know, I never even let my husband do that!"

"Really?" he said and I could almost hear the huge smile beaming on his face, then regretted saying it.

"So?" he said, "What else doesn't he do?"

Looking over at his naked body, I noticed 'he' was coming to attention again.

"That," I said, grabbing the shaft and helping him up.

Smiling, he sighed contentedly as I worked on him, the intense hunger between my legs suddenly returned stronger than before. Looking at him closer, it was definitely thicker than Mike's and may have even been slightly longer.

Positioning himself on his side as I held on to him he leaned forward and kissed me again. His tongue probed my mouth as I returned likewise. Spasms of pleasure again shot through my body with such strong intensity I felt I might lose consciousness.

"God! You are so hot," he whispered returning his lips to mine.

Moving his hands to my breasts, he gently massaged them, occasionally pinching the nipples sending more currents coursing through my body.

Turning me over, Ian began massaging my back gently moving himself back and forth. Feeling his solid member touching my back as he leaned forward again opened the gusher between my legs. Next he positioned himself so his staff was between my already slick buttocks. Adjusting himself so he was now between my legs, he grabbed my waist and began gently pulling. To help, I lifted myself giving him full access to me again. Running his cock between my asshole and pussy to tease me, he then inserted himself in me again. This time with slower, gentler strokes he plumbed my depths from behind. The sensation was so wonderful I quickly climaxed again. Giving me time to recover, he then lifted me up to my knees as he continued to pump his stiffness in my hot mound.

While he fucked me from behind, he reached around and grabbed my breasts again. Suddenly, he stopped and withdrew, as an audible sigh of disappointment escaped my lips. Leaning towards my ear, he whispered, "This time, it's for you."

Turning over, I grabbed his shoulders and moved him so he was now on his back. "In that case ." I said. Leaving the sentence incomplete, I straddled him, grabbed his hot cock and inserted it into me again. Pumping up and down, with my boobs bobbing around I got lost in the lust. Feeling his hands on my hips trying to push me off, I realized he must be close to his second climax of the evening. Pulling myself away, I maneuvered my head so I could take him in my mouth again, without having to be asked. Grabbing my head, he thrust up one more time and shot his load deep into my hungry throat again. As he began to recede from my mouth, I continued sucking and licking him savoring every drop. With each swallow, the grossness factor subsided a little.

After cleaning him up, I straddled him again and inched my way up. Stopping at his well developed chest, I kissed and licked him all over while rubbing his shoulders and biceps. Laying on him as he gently rubbed my back, I glanced out the window and noticed the sun was beginning to rise. "Shit!" I said, "I'm not ready for tonight to end!"

"Hey," replied Ian, "we don't have to be out 'til noon."

"Good, 'cause there's something else me and Mike've never done."

"Yeah?" an obviously worn out Ian said. Soon after he fell asleep, while I lay there beside him running out of juice myself.

As I began to fade out into slumberland the events of the night race through my head and the realization of what had happened fell on me as if the roof had collapsed.

Looking over to Ian, his eyes were closed, but he had a big contented smile on his lips. I felt like the polar opposite. Not only had I betrayed Mike, but I taken advantage of our best friends' son. Suddenly, I felt on the verge of tears, that oddly enough never did come, I did feel an intense hollowness in the pit of my stomach though and wished I could have a good cry. How can I face any of them again? Should I confess? What do I do now? With that last thought, Ian jostled and turned towards me putting his arm across my chest. I continued to lay there and eventually was able to drift off for a fitful couple of hours sleep.