Emily's Big Night Out

My husband Brent and I live in a nice neighborhood in Sarasota, Florida. Our next door neighbor, Beverly, Bev for short, is my best friend and a single mom of an 18 year-old son, Jeremy. The truth is, Brent is away so often on business that I often feel like I’m single myself, although fortunately we don’t have any children of our own. When Brent is away, Bev and I sit on my back porch near the pool amidst the bright pink hydrangeas and bougainvilleas and commiserate on our aloneness. Sometimes Jeremy will come over and swim while we talk. Jeremy is a good looking kid, tall and athletic with coal black hair. Bev says he looks like his father who was supposedly some New Yorker of Sicilian descent who just refused to grow up. She dumped him when she found out that he had had numerous affairs, one with a 14 year-old girl they had hired to watch Jeremy when he was still a baby.

One afternoon, our discussion turned to my lack of an escort for a formal awards banquet at the university where I teach communications. I had won a prestigious award from a national association and as much as I wanted to attend, I felt it would be a little awkward since there was supposed to be dinner and dancing after the presentation. There would be poor little Mrs. Bennett sitting there with no one to dance with. Brent had agreed to go with me at first, but then backed out when he learned he had to go to China to deal with one of his import clients instead.

“This might sound a little weird,” Bev was saying, “but why not ask Jeremy if he’d be interested in going.”

I suppressed a giggle. “Come on,” I chided, “you can’t be serious.”

“I am serious,” she said in a low voice so as not to be heard by Jeremy who was floating on his back at the far end of the pool. “Look he’s always complaining that I don’t treat him like an adult, not that there’s a chance for him to act like one. I mean, look it’s not like I have to worry about him; he’s with you. It’s an innocent banquet, not like a date or anything.”

“Well, I suppose so, but come on, he’s not going to be interested in going to some dumb old banquet with his mom’s friend – how embarrassing do you think it would be for him?”

“Emily Bennett, don’t you dare sell yourself short,” she replied feigning anger. “You’re an attractive woman, you don’t look a day over 30 and I think any young guy would be flattered to go anywhere with you on his arm.”

“I thought you said this wasn’t a date,” I challenged, from beneath raised eyebrows.

“You know what I mean,” she said brushing it off.

I had to admit I was intrigued by the idea. He was a good looking kid, definitely the type I would have been interested in high school. I would look very much the cougar walking into the event with a young stud like him in tow, and the thought was titillating. Still, I wasn’t sure that he would be all that thrilled at the prospect. After all, I was 38, and despite Bev’s assurances, I was starting to show my age. My hips were a little wider and my breasts a little less firm than they once had been. It wasn’t all bad though, I still had terrific legs and although my face had a few more lines than it had in high-school, it was nothing to sneeze at.

“Jeremy,” Beverly said loudly enough for him to hear, startling me. “Come here please, Miss Emily has something to ask you.”

I blushed realizing she was forcing me into action before I had even decided that I was going to do it. Jeremy sauntered over in that confident way high school boys tend to do when they are trying to appear cool around “mom and her friends”.

“Yes ma’am,” Jeremy said politely standing in front of my chaise lounge awaiting my question.

“Well, ahem, Jeremy this might sound strange, but I was wondering if you would be willing to be my escort to an event I have at the school two Saturday evenings from now. I … I had asked my husband, but you know he travels a lot and unfortunately he’s going to be out-of-town that weekend, and I’d really prefer to go with someone.”

“Well, uh, I guess it’s alright. What kind of event is it?” he asked. I couldn’t tell if he was flattered or not, but I certainly hoped so. My ego was already buoyed by the fact that he had accepted so readily without even knowing what the event was.

“It’s, uh… it’s a banquet,” replied, embarrassed by my stammer. Jeez, I was acting like a giddy school girl being asked to the senior prom, and I was not at all comfortable with the situation. “Of course, there’ll be dinner and dancing afterward, which I why I would like an escort, but I don’t want you to feel obligated just because your Mom and I are friends.”

“No … no,” he replied. “It’s not that, I just was kinda wondering what I should wear and all.”

“Oh, I would imagine a nice suit would be fine.”

“OK, I guess that’d be cool,” he replied and then sauntered off as if it was the most common thing in the world for his mom’s friend to be asking him out … to a function, that is.

“Well, there you go,” Bev said, “told you he’d be fine with it.”



* * * * *



The intervening two weeks flew by agonizingly quickly. I felt as if I were approaching a date with the executioner. It wasn’t that I wasn’t eager to go with Jeremy; in fact, it was just the opposite. I was positively thrilled by the prospect. But that was the problem. I was a married adult, supposedly able to control her emotions, and here I was acting like a 16 year-old with raging hormones. I was positively disgusted with myself.

Finding a dress was an adventure in and of itself. Designers don’t really make dresses that say sexy and matronly at the same time. “Conservative,” said my sensible side, elegant, but not too suggestive. All the while my heart was telling my brain to shut the hell up and pick up the sparkly little red number with the top cut down to there and the slit, cut up to … well, you get the picture. Fortunately, sensible won out, but just barely. I selected a sleeveless, calf-length oyster-toned formal with a pretty lace shawl to cover my bare shoulders. It was understated and elegant, but the lace details hinted at the sexuality underneath – perfect for the evening’s events. I also picked out a pair of strappy sandals with 4 inch heels and a delicate rose detail. Some men were shoe guys and some weren’t, but I thought they were very sexy and I figured every little bit would help.

The weekend of the banquet Bev was going to be out-of-town visiting her sister in Miami. No big thing really, since Jeremy was more than able to look after himself. Still, she asked me to keep an eye on him over the weekend. Motherly concern had always been her strong suit.

If this was a real date, of course, I would have expected Jeremy to drive and come to the door to pick me up, but after all I had asked him, not the other way around, and besides, as I kept trying to convince myself, this wasn’t a real date. So I just popped next door.

“Wow, Mrs. B, you look … you look really good,” Jeremy managed to stammer out as he opened the door for me.

“Why thank you, good sir,” I said putting on my best mock elegant accent, and twirling for him to see the total package. “And you don’t look so bad yourself.” That part was true enough, too. My neighbor’s son cleaned up nicely and clearly had good fashion sense. He wore a blue suit in an expensive fabric with a four button jacket to accentuate his athletic frame.

“You really think so?” he asked, turning this way and that in a feeble attempt to examine himself.

“Of course,” I answered. “Why wouldn’t you think so?”

“Well, Mom bought the suit for me and I’m just not used to wearing suits, I wanted to make sure I don’t look stupid.”

“No you look fine,” I answered. “Better than fine.” He smile sheepishly, apparently accepting my assessment. “Shall we go,” I asked offering my arm. It took him a second to figure out what was going on, but he quickly took my arm and we were off.

Throughout the drive to the conference center where the banquet was being held, I kept sneaking glances over at my hunky “date”. He was clearly nervous – but in a cute kind of way. I was hoping that I was the one having that effect on him, not just the fact that he was going to his first “adult” event. “Don’t worry,” I said, reaching over to pat him on the hand. “You’ll do fine.”

And that he did. He conducted himself quite well, going so far as to open doors for me and hold my chair while I sat. I thought such gentlemanly manners had gone the way of the dinosaur, but my friend had taught her son well. Any girl who was silly enough to break up with this kid, didn’t know what she was missing out on. If only I could train my husband so well. When the time came to dance, I had to do a little coaxing to get him out on the floor, but he did a nice job there as well. It’s not as if we could have been on Dancing With the Stars, but we held our own. By the time we left, I was a bit more giddy with the wine than I should have been, so I wisely decided to let him drive us home. I didn’t think I was past the legal limit, but it was better to be safe than sorry. I could just picture myself calling Bev in Miami to bail me out of jail for DUI, and with her son in the car no less.

“Thanks for the treat Mrs. B., it was a lot of fun,” Jeremy said, climbing out of the car.

“Why don’t you come inside,” I offered. “It’s still early, we can talk or watch TV, whatever you want, I’d enjoy the company. I might even find a couple of wine coolers or some beer, I don’t guess your mom would mind you having one beer. Unless, of course you’d rather go home.”

“Well, I guess I could come in for a while,” he said shyly.

I unlocked the door and he followed like a puppy. I don’t know what he expected, and to be completely honest, I didn’t quite know either. That said, there were three irrefutable facts: 1.) My husband was out of town and wasn’t coming back any time soon; 2.) Jeremy’s mom was out of town and wouldn’t be back until Monday; and 3.) I was horny as hell and my neighbor’s son was looking really good to me right about then. “Come on back,” I said nonchalantly, leading him back to the master bedroom. He politely waited in the bedroom while I went into the dressing area just outside the master bath. I had to get this damn dress off. Oh, it was nothing sexual, it just felt so confining. If it gave Jeremy other ideas, well, then that was just an unavoidable consequence, wasn’t it. I moved my hands to the zipper at the back of my dress, carefully eyeing Jeremy in the mirror which gave me a complete view of the bedroom. I tried not to let on that I was watching, and I don’t think he caught on.

“Uh, Jeremy,” I called, pretending to be having trouble with the zipper. Of course, I was quite capable of unzipping myself, but what would be the fun in that. “I was wondering if you could help me with my zipper?”

“Your zipper,” he half-gasped.

“Yes, I seems to be stuck.”

“Well, ah yeah, I guess … I guess I could.” He stepped up behind me and drew the zipper down and stepped right back out before I could even lift the dress over my head. Dropping the dress over the stool against the wall I stepped into the room dressed only in a half-slip and my underwear.

“Uh, Miss B., this is, I don’t think ….,” he stammered at a loss for words.

I laughed uneasily, “Come on, Jeremy, you’ve seen me with less on out by the pool. This shouldn’t bother you. Besides, I just want to be comfortable.” I paused, trying to think of something creative to say, but my mind was drawing a blank. “So you graduate next week, huh?” I asked stupidly.

“Yeah, it’s going to be weird finally not having to go to school unless I choose to.”

“Well, you are going to college, right?” I asked. “Your Mom said you got accepted to the University of Florida.”

“Yeah, I mean, I’m starting in the fall and everything, but it’s like I’m not being forced to go to school and all, like high school.”

“Where is Kit going to school?” I asked, mentioning the name of his latest girlfriend. Bev had told me the Jeremy and Kit had broken up about a month ago, but I wanted to confirm it for myself. Kids were so fickle, they broke up and got back together all the time, sometimes without even bothering to mention it to their parents.

“Ah, who knows,” he huffed. “She said she wanted to go to Florida, then South Florida. It doesn’t really matter anymore, I guess. We broke up about a month ago. I haven’t even talked to her since.”

“Oh, I’m sorry.” I said, feigning genuine concern.

“No,” he said without much feeling. “It had been a long time coming; I guess I just didn’t want to see it. I’m better off without her. Even my friends were telling me I needed to get rid of her. It’s like one minute she cared about me, the next it was all about her. I don’t think she was ready for a serious relationship anyway, she wasn’t mature enough.”

“Well, it’s very mature of you to see that and be willing to make the tough choice and let her go … although, I think she’s crazy if you ask me.”

“Huh?” he asked, not getting my drift.

“Look, Jeremy, I’ve known you and your Mom for a long time now, right?”

“Yeah.”

“I’ve seen you grow from a little boy into a young man, and I can see that you’ll make a fine husband to someone one day. You just need to find the right woman, one who will value you for all you have to offer.”

He began to blush, turning away to hid the flushing of his cheeks and I saw my opening. I crooked my right index finger and placed it gently beneath his chin, turning his head to face me, and lightly, but insistently kissed him on the lips. “Oh … uh,” he stammered and swallowed hard as I drew back. I had clearly left him at a loss for words.

I suppressed a giggle. “I’m sorry,” I said, “I didn’t mean to leave you so flustered. I don’t know why I did that, but I’m not sorry I did; and I do deserve it, after all. What kind of date ends without the girl at least getting a good night kiss?”

“Well, I … it’s not that ….”

I laughed out loud and shook my head, “It’s okay, Jeremy, believe me, I understand. It’s not cool to have your Mom’s friend kissing you. I just thought maybe … well, maybe the night might not be complete without the goodnight kiss. Besides, you earned it. You were a very good escort.” I swung my legs off the bed and was about to get up. At least I had given it a shot. Truth was, I shouldn’t have expected anything different, I was crazy to have thought Jeremy would be interested in me. Besides, it was wrong to be going after him like I did; he was still practically a child.

To my shock, Jeremy grabbed my from behind before I could get up and pinned me down by the shoulders and kissed my violently his tongue probing relentlessly. After recovering from my initial surprise, I willingly reciprocated. I had to admit he was a good kisser, surprisingly good for being only 18. I thought despairingly of my husband. Brent was 40, and he still couldn’t kiss worth a damn. It soon turned out that Jeremy was also very persistent. It was a full five minutes before he let me up to catch my breath.

“Wow … uh, well … now it looks like I’m the one who’s speechless,” I managed to spit out, breathing heavily.

“Look, I’m sorry … Miss Emily, I didn’t ….”

“No need to apologize, Jeremy,” I soothed, putting my fingertip on his lips. “It’s fine. I liked that. In fact, I was sort of disappointed when you didn’t respond immediately. I thought you were embarrassed that I kissed you.”

“No, it’s just that it was so sudden and unexpected. Miss Emily ….”

“Just Emily,” I said. “Please. It feels weird when you call me Miss Emily, especially after what we just did.

“Uh, okay … Emily. It’s just that … well, I don’t know exactly how to say this, so I’ll just tell you. See,” he sighed, “I’ve been kinda been thinking about you for a long time. You’re so pretty, and I … well, I sometimes wish I was your husband. He’s gone a lot and I think he’s crazy to be leaving you here all alone. That’s why I agreed to go with you tonight, I figured that it would be really nice to be able to be out with you, even if it wasn’t really a date. I never … I never expected this to happen.

“Really,” I asked, incredulous, my eyes brimming with tears of happiness.

“Yeah, really,” he confirmed.

“Oh God, Jeremy, you’re so beautiful,” I responded, kissing him deeply once again. I couldn’t believe it was really happening. The decision to give myself to him wasn’t even difficult, but I knew we would have to be careful. His Mom wouldn’t be home to miss him, and Brent wouldn’t be home for days. We could spend the night together, but what about in the future. We would have to tread carefully, but I couldn’t see giving Jeremy up, not now. “Jeremy,” I half-whispered, looking down on him from my dominant position, lying halfway on top of him. I stared him straight in the eyes so he could see I was serious. “I’m yours tonight. Anything you want to do with me you can do; but, that’s all, tonight only. I’m not saying that it’s going to be that way forever, but I need time to think things through. Your Mom, and my husband, I have to figure out how – or if – we can work our way around them. Brent shouldn’t be too hard to fool, hell, he’s never here anyway; but your Mom is another story. She knows me too well, and if we start sneaking around, she’ll know something’s up for sure.”

“Uh, oh … okay, I guess,” he responded.

“I’m serious, Jeremy ,” I reiterated. “Nod if you understand.” He nodded. “Good. Now, you’ve got me. What on Earth are you going to do with me?”

His response was tentative at first. No surprise really. If you were an eighteen year-old boy and just been given the green light to do whatever you wanted by a beautiful – well, okay looking, anyway – half naked lady. You would probably be confused by the mind-boggling array of options as well; or maybe he just didn’t know if all the boundaries were REALLY taken away. In any event, his initial move was simply to kiss me again. I tried to be as responsive as possible to make it clear that I wanted him, wrapping my arms around his powerful torso, lightly running my glossy, long nails up and down the broad expanse of his back. “Oh, Jeremy,” I whispered into his ear. He backed away, and my heart dropped thinking I had pushed him too far too fast. To my relief he, stood up and removed his shirt, slacks and socks, climbing back on the bed clad only in a pair of thin boxer shorts. I thought that was sort of cute, he was a shy one, but I wanted to see what was beneath the blue plaid fabric.

I pushed myself up so that we were both on our knees facing each other. I reached one hand out to caress his cheek. He responded by putting his hands on first my shoulders, then allowing them to slip down around behind me. I could feel him fumbling with the clasp of my strapless bra, and thought about helping him, but he was a big boy and I was sure he could figure it out on his own. There was something sinfully erotic about allowing him to take total charge; and after all, I had promised to give myself to him, I was his to command.

As my bra dropped onto the sheets, Jeremy lowered his head to my nipples. Oh, he had done this before. Skillfully he nibbled at the areolas and pinkish nubs the as his fingers gently caressed the milky flesh around the perimeter. Oh yes, Kit was definitely going to be disappointed. Not every guy was this skillful as she would no doubt find out, much to her disadvantage. I grew faint and slumped back against the pillows, pulling my young lover along with me.

He looked me in the eye. “I want to make love to you,” he whispered. Ah, so courteous. I suppressed a giggle, this was fun. I decided to shock him.

“I don’t want to make love to you, Jeremy,” I replied in as sultry a voice as I could muster. His little face clouded over momentarily as if I had just told him I was taking a toy away. “I wanna FUCK you,” I continued, placing special emphasis on the word fuck. “Fuck me, Jeremy,” I said more loudly to increase the effect. “Fuck me hard. Fuck me now.” I reached down and literally tore his thin boxers from him to put an exclamation point on my demand. I was not disappointed by the sight of his stiff member. It was not gigantic, but it was discernibly longer and thicker than my husband’s. Fortunately, he responded well to orders. I wanted him to take charge, I wanted for him to use me, but sometimes with boys it takes a little prodding.

He yanked my slip and panties down, leaving my shoes and stockings in place. I was a little surprised at first. In my experience, boys his age seemed to be interested in getting a girl as naked as possible in as little time as possible. I seemed like it was mostly older men whose tastes were refined enough to appreciate the eroticism of sex in high heels and stockings. I spread my legs wide, anticipating his cock, but once again I was surprised. Instead of sliding his cock into my expectant pussy, he moved his head down between my thighs. Jesus, I wanted his cock inside me. There was plenty of time for this later. But he was insistent, burying his face in my mound, his tongue probing the folds of my sex. Instinctively, I grabbed his head, entwining my fingers in his hair and guiding him to exactly where I wanted him. I felt a fluttering in my belly as his tongue thrashed at my clit, driving me insane. The first wave of my climax hit me harder than I expected as my eyes rolled back in my head and my fingernails dug into his scalp. Undeterred by the pain, he continued to lap at my slit until I came again with an animalistic groan, squirting a thick stream of my juices into his face.

Enough!

I clawed at his back, willing him forward, finally being rewarded by the feel of his cock throbbing against my inner thigh. My fingers guided his rod to my aching cunt, positioning the tip at my entrance. “Push baby,” I gasped, and he pushed forward. His girth was so unexpected that I cried out and grabbed at the sheets, clutching them tightly in my fists as he penetrated me. He was much bigger than I thought, so much so that I could feel the very tip of his member bottoming out against the opening of my cervix. Our lips met again as he began moving within me. Instinctively, I wrapped my legs around his hips resting the heels of my shoes on the backs of his thighs. Brent always loved the feel of my silky legs wrapped around his hips and the way I dug my heels into his thighs when I came. Jeremy filled me so completely that I knew I would be spoiled forever. No way Brent would ever feel this way. Jeremy’s talent was limitless as he withdrew almost all the way on each sensuous stroke before plunging back in to the hilt. He varied the angle with which he entered me so that each time he thrust in, it was a new adventure. “Oh, yes, baby,” I cried over and over again. I was near tears as my emotions overtook me, I was loving it. “Oh, God” I shrieked, so loudly that I was worried the neighbors would hear, and a double-shot orgasm rocked me to the core, the second wave nearly causing me to pass out. I dug the heels of my sandals into Jeremy’s thighs like spurs and he groaned as I felt his cum jetting into me, I let loose with a torrent of my own, our combined fluids gushing out from between my thighs and pooling on the sheets below.

As I was basking in the warm afterglow, Jeremy rolled off me, his wilting member sliding out of my well lubricated hole. “My God, that was wonderful baby,” I smiled, gently stroking his cheek with one hand, then allowing it to fall to his nearly hairless chest, soaked with a thin sheen of sweat. “I know a woman is not supposed to ask …but how do you …” I didn’t finish.

“I dunno,” he shrugged. “I guess I just try to imagine what I would like if I was a woman, ya know.” He chuckled at himself, “I know, pretty dumb, huh?”

“No, no, not dumb at all. You know, I never cease to be amazed at your maturity.”

He just shrugged.

“Well,” I said sliding my head down his chest, “there’s one area where I’m glad you’re not so mature. A young man like yourself is supposed to be able to regenerate quickly.” I stuck my tongue out and licked his flaccid shaft, attempting to coax it back to life. I wasn’t done yet. It responded quickly to my ministrations and sprung to attention. Drawing it into my mouth I proceeded to give him the blow job of my life. I had never done this for Brent. Oh, I knew how to give one, it was how I had managed to remain a virgin as long as I had in high school. There was just something repellant about his cock and I had never had the slightest desire to put it in my mouth, but I felt drawn to the young member I was now working so diligently on. I stared up at him from beneath my heavily mascaraed lashes, trying to appear seductively coy. Each time I pulled his cock from between my lips, I allowed a thin strand of saliva to connect his engorged shaft to my lips. God, it looked so slutty and nasty, and I was in heaven.

I didn’t know if he wanted me to suck him off of not. I was certainly willing to do so. I really wanted him in my pussy, but we had all the time in the world for that. As if reading my mind, he looked into my eyes and stated in a low, commanding voice, “Get on your hand and knees for me.”

His wish was my command, and truth be told, I loved being fucked from behind. I tended to be able to get it so much deeper that way and it hit my G-spot just so. Cumbrously, I shifted position, propping myself up on all fours, spreading my thighs slightly so that he could fit in between my legs without a problem. His hard cock butted up against the swollen lips of my labia, and I felt a trickle of lubricating fluid leak out. The tip of his cock parted my folds and slid easily inside me, as a groan of pleasure escaped from my lips. Ever so slowly Jeremy fucked my hungry cunt. It seemed as if I could feel every bump and vein on his hardened shaft as it pistoned relentlessly in and out my channel.

I felt a strong hand reach around and a finger probing at my clit. “Jesus,” I cried as the digit found the nub buried within the folds of my slit and began to toy with it. He sensed my increasing reactions to the pleasure I was feeling and responded by thrusting harder and faster. I was now moaning with each powerful stroke. I was going to go out of my mind if he didn’t stop. “Ungh, oh baby, yes,” I repeated over and over, letting him know that he was doing it right. When I felt my climax approaching, I realized that I wanted him to cum with me, so I yelled words of encouragement, “Yes, baby, cum. Cum with me, baby. Cum, cum, cum,” I cried, the words reverberating off the walls.

My entire body seemed to glow with pure sexual energy as I exploded in a wonderful climax, the muscles of my cunt tightening around his wonderful cock. Instead of cumming inside me, however, he withdrew and spurted jet after jet of his milky seed onto my ass and back, getting it in my hair and on the sheets in the process.

Unable to go any longer, I collapsed onto the sweat and cum soaked sheets, falling into a deep, satisfying sleep.

The sunlight streaming in through the sheer curtains hurt my eyes as I tried to focus. At first I thought I was dreaming, I was back in my old office, and the phone kept ringing and ringing. Ringing. The phone was ringing. I propped myself up on one elbow. The bed was a wreck and the room positively reeked of sex, my juices and Jeremy’s some of it dried on the sheets, some still damp to the touch. He was still curled up beside me. Hm, the kid could sleep through anything. Might be useful to know. I reached over and grabbed the receiver. “Hello,” I answered, knowing that I still sounded groggy.

“It’s 11:30 and you’re still in bed? That must be some kind of record for you.”

“Huh?” it took a second to register, then it hit me, Brent!

“Yeah, Miss Early Bird,” he joked. “You’re always coming down on me for being such a late sleeper what about you? I guess when the cat’s away …” he trailed off.

“Where are you?” I asked. “In Beijing it must be what, midnight?”

“Yep, in Beijing it is almost midnight, but I’m not in Beijing.”

“What?” what had I missed.

“Yeah, I’m back home. In fact, just leaving the airport now, should be home in 20 minutes or so. Business deal with the Chinese fell through, damn Chinks. That’s okay though, because I met a guy from Chicago, he’s willing to take the deal I was offering to the Chinese and it ends up being cheaper for me since I don’t have to worry about shipping shit halfway across the globe.”

“Shit!” I exclaimed under my breath.

“What was that?” he asked.

“Huh … oh, nothing,” I replied.

“Hey, well don’t worry about getting up on my account. In fact, I might just be tempted to crawl in bed with you when I get there. It’s been a long time baby.”

“Uh, yeah long time, heh.”

“Traffic is really light, looks like. I might even make it home in record time,” he breezed.

“Yeah, well, babe let me let you go,” I said.

Time to set some record times of my own!