Chapter 4: We take a huge risk
I mentioned my friend’s family was well off, and because my large family didn’t make a lot of money, I think THEY had a “soft spot” in their heart for me. So they sometimes took me along on family trips and vacations and the like.
In my 18th year, they decided to take a golf vacation to Kentucky and I was invited along. It had been quite a while since my handjob fantasy was fulfilled by Ms. Nancy, and once again, I was wondering where I stood with her. I eagerly snapped up the invitation, and soon we were driving together to Kentucky for a golf vacation.
I am sure you can imagine the several hour trip was excruciatingly frustrating for me. I sat in the back, behind her husband, and my best friend sat behind his mom. This beautiful woman, who had watched me cum, not once, but twice, and had made me cum while watching her jiggling tits was now mere inches from me and staring from the back seat, I could see the beauty of her face and watch the curve of her breasts in the “comfy” t-shirt she wore on the trip. Unfortunately, she was wearing a bra, so the road bumps were of little benefit during the trip. Still, just being this close to my long-time masturbation fantasy and reality had my hormones churning.
The drive was lengthy and exhausting, but at last we arrived in Kentucky and were introduced to the family in whose home we would be staying. They seemed like great people, and I knew I would be comfortable, even though I was the lone friend invited along on the trip. Our hosts had a home on the golf course. Their residency in the neighborhood included golf privileges for them and their guests, which meant we were going to get to play a lot of golf.
We were all big into golf, especially Larry and me. I probably played as well as I ever had, every once in a while beating Larry, who was an excellent golfer. Something that seldom happened.
Larry and I awoke at the crack of dawn each day to play. The older folks would go out later, because they did a great deal of drinking while on vacation and probably woke up hung over every morning. Whatever the reason, Larry and I were usually done by the time the older folks got ready and went out to play.
This doesn’t mean I didn’t get my opportunity to see the object of my many teenage fantasies. I got to see her late each morning as she and the other women (some of whom were not so bad either) got ready to go out on the course.
Ms. Nancy played golf in what they call a skort, which is a combination skirt and shorts, and a form fitting, but modest, polo shirt. She had great legs, a sexy mature woman’s rear end, and of course, those fabulous C-cup breasts protruding from her polo. She wore her hair fairly short, nice sexy lose curls about her face, and her makeup and lipstick were always perfect. She had beautiful green eyes and long eyelashes that could literally make your knees buckle as she stared into yours.
I couldn’t seem to take my eyes off her whenever we were together. I walked around with a constant 18 year old’s hard-on, thanks to her, and I am guessing that, if no one else noticed, the smirk she gave me every time we spent just a bit of time together was proof that she noticed my reaction to her. She was discreetly flirtatious, batting her eyes and smiling at me with those pretty white teeth whenever she could get away with it. Women seem to be good at this. Of course, I did the same to her, though it was probably a clumsier effort.
Still, there was virtually no opportunity to be completely alone with her. I think it was her conscious decision, as there were too many people around and I am sure she didn’t want to be caught alone with an 18 year old “boy” hundreds of miles from home. The shame would likely have been palpable. Thinking back, I’m not even sure how I would have gotten home. Even in my young mind, I was able to reason through these things and understand why, despite her many smiles, discreet glances, and biting a nail occasionally, nothing overtly sexual occurred during the first few days.
I, of course, was perpetually scheming to find a way to get the two of us alone. It occupied my mind increasingly as the week wore on and as I became more sexually frustrated. I was perpetually hard, but I resisted relieving myself on the off chance that we might find a few minutes to be alone. My sexual frustration affected my concentration, which affected my ability to scheme to find a way to be with her. As the week wore on, it also affected my golf game.
It had been a long week and Larry wanted to play 36 holes on Friday. We were scheduled to leave Saturday mid-morning, and we both wanted to play a lot that day. I was awful, barely breaking 90 both rounds, I was frustrated, I was thinking about a certain beautiful woman, I was thinking I wanted to cum, and I had been unable to fulfill my sexual desires. In my head, “damnit!” was the only thing I could think. If Ms. Nancy had a strategy and wanted me anxious and frustrated, well, antalya escort it was working.
That evening, after a delicious home cooked dinner prepared by their friends, Larry and I retired to the downstairs gameroom and played some pool (dude was a competitor, wanted to win at everything). In my sexually frustrated state, I was no competition and he won at pool, then dominated me in a game of nerf basketball. He wanted to play some more, but I said “No, let’s watch TV and then I’m going to bed.” My crotch was throbbing. I was hard as a rock, and I had had no satisfaction, despite being mere feet from my fantasy woman the entire week.
We were watching some mundane network program (back when we only got three channels) and I began to drift off to sleep after a long day and a hearty meal. I stood up, yawned, stretched, and said “I’m going to bed.” I was pissed about the way the week had gone. I had been mere feet away from this goddess, this vision, this masturbation fantasy and handjob maven for several days, a woman I desired and that I knew desired me, and yet had been unable to act on it at all. My best friend didn’t seem to notice my attitude, but he was, I think, a bit naïve and wasn’t really paying attention. He was interested in girls, young ones with perky breasts and tight cute teenage butts.
He could have them, I was only interested in the big breasts of his mom, her sexually mature rear, and those wonderful thighs.
I headed to the bedroom and lay down in my twin bed. Looking over at the clock, I saws that it was after 11 p.m. I heard the sounds of The Tonight Show from the other room. Larry was still watching. I began to doze off.
Probably about 20 minutes later, I heard the TV switch off and my best friend walked into the room and lay down in his bed. There were two twin beds in the basement bedroom that we were using. Having been awakened from my brief nap, I wasn’t ready to fall back asleep, so I listened to
Larry’s breathing become that slow, regular rhythm of a deep sleep. He was out cold. The guy did everything to the max, so I wasn’t surprised he was exhausted.
In my frustrated state, sleep wasn’t coming easily for me, and I began churning over in my mind where things stood with Miss Nancy. Was she done with me, was she through taking the risks? Had she “kicked me to the curb,” so to speak? I initially thought that my desires weren’t really love, but more of an extreme sexual attraction. But I desired no one but her. I hadn’t really looked at other women, I hadn’t thought about other women, I hadn’t been with other women. And there had been opportunities. She was all I wanted. Perhaps I was in love with her. My 18 year old brain struggled to understand the feelings I had.
My bed had heavy covers, a sheet, a bedspread, and a quilt on top. And yet, through all that, in the faint light of the bedroom, I looked down and saw this gigantic tent created by my hard on. “Wow,” I thought, “this woman has really had an effect on you.”
After probably a couple of hours of churning these issues over in my mind, I passed into the fitful sleep of a sexually denied and frustrated 18 year old.
The faint creak of the door hinges as the door to our bedroom slid open made me sit up and turn toward the door with a start. There was a very soft patter of tiptoes and as my eyes adjusted to the light, I could make out the vision of my fantasy walking softly toward me. In the dim light, I could see she was wearing white lingerie that came to about mid-thigh, and stockings.
Having been awakened from a light sleep, I was a little confused. She approached me, put a delicate finger to my lips, and very, very softly “shhhhd” me. I got the message. We both glanced toward her son, who continued in the deep sinus rhythm of his exhausted sleep.
Ms. Nancy gently lifted the covers and slid into the bed next to me. “We have to be very quiet,” she whispered into my ear. “If Larry wakes up, we’ll both be in huge trouble. Remember, you don’t touch me.” She pushed my hands behind my back. “Lock your fingers together,” she commanded softly.
Her lovely fingers began to trace lines over my face. “So handsome,” she muttered, “have always loved those dimples.” Her touch slid down to my shoulders and chest and she whispered again in my ear “No matter what happens, no noise!” I nodded my understanding. Finally her fingers worked their way lower and lower, touching my belly, then my upper thighs. She slipped aside my boxers and began to gently tickle my balls. I exhaled contentedly.
She put her lips next to my ear, kissed me, and whispered “I’ve made you so frustrated this week, haven’t I? But until tonight, there was too much happening. Jack’s on vacation, and when he’s on vacation, he wants a piece of ass every night. I have to take care of my husband’s needs first, then I can focus on mine. Tonight, I fixed him 3 bourbon and cokes, gave him a blow job, and he’s dead to the world.” Her fingers continued to lightly rub my swollen alanya escort testicles. I’m not sure how much of what she said I took in, my mind was roiling.
“Now it’s my turn,” she whispered. “I took care of my wifely duties, now I’ll take care of my wifely needs. I think a woman should always have a husband she takes care of and who takes care of her needs, and a desirable man on the side who takes care of her wants”
For the first time that night, I felt the touch of her fingers on my throbbing cock. “Oh, poor frustrated baby,” she whispered, half laughingly, ” have I made you suffer?”
I didn’t respond, I was simply enjoying the moment. She continued, “Well, how about if I make up for it?” With that, she slid my boxers down my legs and took them off, taking care to put them behind me.
“Tonight, you won’t need tissue, or my t-shirt. Know why?” She said softly. I shook my head no.
“Because tonight, you get the treat of your lifetime. I’m going to swallow every drop.”
My heart began racing. My all-time favorite fantasy woman, the hottest mom I’d ever seen, was about to give me a blow job.
Her fingers never stopped tickling and kneading my balls, but she let go my cock, and it continued to protrude straight out, she softly chuckled into my ear “Love your 18 year old cock, Jack’s doesn’t do that anymore, even when he’s on the verge of cumming. “
There was a rustle of covers as she slid her head down toward the middle of the bed, where my aching penis was dying for attention. But being the sexual temptress she was, she didn’t give it any. Instead, she started running her tongue over my belly, then my upper thighs, just above my penis, then she started lathering attention on my balls.
I found this more frustrating than the entire previous week. I kept thinking to myself, “Oh please just touch, just lick, just fondle my cock.” Clearly, Ms. Nancy knew how to heighten the moment, because as I thrust my throbbing hard cock toward her, she avoided it, focusing on everything but.
She briefly reappeared for just a moment, put her lips next to my ear and whispered, “You are about to enjoy the best blowjob of your life. Part of the reason it will be the best is that you will want me to finish it so badly. So stop trying to force me to suck it. I will do that when I’m ready, and when you truly need it.”
She continued her ministrations down my thighs, over my belly, across my balls. My cock was granite at this point.
I think she spent 25 or 30 minutes (OK, it seemed like a week) stimulating me, but completely ignoring my cock. When she was finished, she moved back up toward my face, leaned toward my ear, and whispered “ready, my handsome young man?” All I could do at that point was nod my head yes.
Pulling the covers over her, she slithered back down toward me, gently licked the head of my cock, gripped it firmly at the base, and proceeded to perform the slowest, most thrilling and excruciating blow job one can imagine. She initially slipped just the very tip of the head in her mouth, backed off, and ran her tongue over the head. She pulled back the foreskin and began slow, sexy, lengthy sucking motions. My hips began to respond, involuntarily, thrusting up and down, trying to make her go faster. Her nails gently stimulated my balls which, by now, were pulled taught against my body. I gave a very slight moan in response to her stimulation and she paused, giving a very quiet “shhhh.” I nodded my understanding, and she resumed the slow, sensual, drawing of my cock into her mouth.
She stopped again. I think she wanted to make it last. If she did it was for her, not for me. She ran her tongue very gently along the underside of my penis, then lathered it generously over the tip, took it back in her mouth, back down the shaft, and then back up. She took it back out of her mouth and in a very very soft voice she whispered “get ready,” she whispered. I nodded OK.
Finally, she began a slow, steady, rhythmic sucking of my rigid penis. Up, back down, then up, back down, fingernails gently rubbing my balls, over, and over , with the skill of the clearly experienced woman I had always known her to be.
I felt myself growing closer and closer to the edge, ready to explode, needing this, wanting this, having to have this. I clinched my hands tightly together behind my back as my orgasm approached, knowing I had promised not to touch her (and not wanting to ruin this). Finally, at long last, I kicked my heels into the bed, threw my head back, and began the repeated convulsions of a young man’s forceful orgasm. I couldn’t help it, I groaned, though as quietly as possible, as I felt my cum begin to spurt into this goddess’s wonderful mouth.
I felt her satisfied chuckle as she enjoyed the results of her efforts, greedily swallowing down the jets of sperm I was firing into her mouth. I lost count how many, but my orgasm seemed to last a full minute. I bucked, groaned, and grunted as the wondrous belek escort mouth of my fantasy gave me complete oral satisfaction.
At last, my orgasm begin to subside and she sensed it too. Holding still against me as the last few drops landed on her tongue, she at last slipped my semi-hard penis from her mouth, gave the head a couple of quick licks, making me shudder, then released me. She shifted up toward me, still under the covers, and in the dim light in the room, I could see the pearly whites of her happy smile. She kissed me on the lips, the first time I had ever been kissed by someone who’d just swallowed my cum , and whispered “was it worth the wait?” I nodded my agreement.
I heard her slip off her panties and toss them to the floor. She reached behind me, taking each of my arms from behind my back, turned so she faced the foot of the bed, straddled my head, and lowered her neatly manicured pussy toward my face. “My turn,” she whispered, and placed one of my hands on each of those sexy ass cheeks.
Man, that ass I’d always wanted to grope. Now I was! I immediately ascended back into heaven as she placed her pussy over my lips.
I was 18, I didn’t know my way around a woman’s vagina (didn’t really understand the anatomy), but I was game and willing to do the best I could. The low light and the fact that her powerful thighs were blocking it didn’t help. Still, I thrust out my tongue and began to lick her gently all over that area. She sat still on my face, her sexy ass over my nose, initially, letting me learn her anatomy just a bit, then she began to rock slowly back and forth across my tongue. I continued to attempt to lick her with my tongue.
After several minutes of this, she hmppppphd audibly, lifted herself from my face, bent over and said “Just hold your tongue out, hold it still, and let me do the work.”
I obeyed. Sticking my tongue out as far as I could, I held it still and she began to slip forward and back across my tongue. It was obvious she knew the spots she wanted it to hit. Her initially short back and forth thrusts across my tongue became longer and longer. Her pace became quicker and quicker. Finally, she leaned forward, put her hands on my thighs and, after a few more of her long strokes, she held still, quivered, gave several audible breaths, and began a hard, trembling, shuddering orgasm. I felt her sexy ass rock back and forth over my nose several time. She took my hands from her ass, moved them under her lingerie to her breasts, and rubbed them rapidly over her stiff nipples. A few minutes passed, her trembling began to ease, and I felt her body relax over my mouth.
She raised herself from me, slid back under the covers, then kissed me on the lips and said “It’s only fair I taste myself too.’
Her task having been completed, she slipped quietly from under the covers, felt around on the floor until she found her panties, then retreated quietly from the bedroom. The door hinges squeaked softly as she pulled the door closed.
I lay there for a few minutes completely satisfied, contemplating in my mind what had just happened to me, and wondering where things would go from here. I still had her taste on my lips and tongue, and I could smell her delicate scent. I wondered if it was just my imagination, or if my face really smelled like Miss Nancy’s pussy.
My first orgasm in at least a week, my first taste of mature sexy mom pussy, the kisses, and getting to put my hands on her luscious ass and tits, left my young man’s head, or maybe both of them, spinning.
I stared straight at the ceiling, breathing deeply, contentedly, and smiling inside.
After a few moments, I rolled onto my side toward my best friend. He was sitting upright, looking right at me.
“Let’s talk tomorrow.” He said. And laid back down. In a few minutes, I heard his steady breathing as he fell back asleep.
At that point, I didn’t know what was coming. From my best friend or my best friend’s mom. I soon fell asleep myself.
That morning I woke up to the shower running. Larry awakened before me and had not killed me. I regarded that as a good sign. He exited the bathroom a few minutes later, already dressed, walked across the room and out the door without saying a word to me. He headed upstairs. I jumped in the shower quickly (I have to admit I didn’t wash my lips or brush my teeth) and quickly followed him upstairs. I found him out by the golf cart, loading up his clubs. I walked out and he said “Let’s go.” I loaded up my clubs and we headed out toward our final round.
About half way to the first tee, he let his foot off the pedal of the golf cart, looked at me, and said “I can’t choose between my best friend and my mom. You have to leave her alone, or it will mean our friendship. Your choice.”
“You know my dad will eventually find out and if he does, he will probably kill you, her or both. I can’t have either of those things happen.”
I sucked in a breath and said “Yeah, I know. I guess I’ll have to end it.”
“Yeah. You will.” My friend answered, ” I think last night was her way of fulfilling all your fantasies. It will be easier if you deliver the news to her, without letting on that I saw. I won’t say a word.” We shook on it and it never came up again.