Chapter 3: Dates and Dalliances

Along around the beginning of November an astonishingly strange thing occurred, or at least it seemed strange at the time. It was Friday night and the only one going out on a date was Sue! Both Mom’s and my dates came down with the flu, while Sue announced that she was going to her first high school dance. She was very excited, since this was to be her first ‘date’ date. Mom had said no dating until sixteen but had relented so that we could date once we got to high school, and my sister had been asked by a fellow in his junior year. Bobby Pritzer was a thin-as-a-rail pimply computer geek, but what the hey, it was her love life.

He was picking her up about eight or so, so after nervously trying things on in her room, she called Mom and me in and asked, “So, how do I look?”

Mom didn’t say anything right away, and I kind of simply stared. I guess I wasn’t too tactful when I replied, “You’re wearing that?”

Sue got really red and demanded, “What’s wrong with what I’m wearing?”

Sue was dressed quite casually, but not what I like a woman to wear on a date. Her baggy black jeans did not cover the fact that her shoes were black Doc Martens, and her oversized red sweater had a wide neck, so that it tended to sag off one shoulder, exposing a plain white bra. “Nothing,” I said, “if you want to hang out at the mall with your friends. I thought you were going out to a dance.”

“Mom!” she screamed.

Mom looked at me disapprovingly, but before she could say anything I used The Power. {Work on her, }I thought to my mother. {Dress her up in something pretty and sexy. Lose this get-up.}To Sue I thought, {Listen to Mom. Cool down.}

“Now dear, I really think your brother, in his cruel and tactless fashion, has a point. This should be a big night, so maybe we can find something in my closet for you. I’ll just bet we’re close enough in size that I have a nice dress for you.” Mom took Sue by the elbow and began propelling her down the hall to her room. I tagged along.

“A dress? But I don’t have time to get all dressed up. Bobby’ll be here in fifteen minutes!” Sue complained.

“What’s his number?” I asked. Sue stared for a second, then told me his number. “Watch and learn,” I said.

Going to Mom’s bedside table I picked up the phone and called the Pritzer’s. Bobby answered. “Bobby, Paul Harron, how you doing? Listen, my sister asked me to call, she’s running a bit late, she needs you to come over a half hour late ... No, no problem, she’s just getting all dolled up ... I am not bullshitting you Bobby ... Yes, she’s going to look like a million bucks ... Now listen Bobby, I would suggest you wear something decent, you know, a suit or jacket, and a real shirt with a real tie ... Fuck you too my friend ... So what if I’m lying to you. What’s the worst that could happen, you take off the jacket and tie. But if I’m telling the truth and you look skanky and she’s gorgeous, you look like the asshole that you are ... Same to you ... See you at eight-thirty ... Bye.” I turned back to my family and said, “There, problem solved. And you, sweet sister mine, are now obligated to get dressed up.”

Sue looked daggers at me, and Mom told me she didn’t like my language, but she said it with a smile. I grabbed my cane (I had just graduated to a single cane) and wandered down the hall. I was downstairs when the doorbell rang, right on the dot at eight-thirty, and opened it as Mom came down the stairs. I let Bobby Pritzer in and was pleased that he had dressed up as well as his geekiness allowed. At least he had on a shirt, tie, and jacket.

“Hi, Bobby, Sue is still getting ready,” said Mom. Looking up the stairs, she called out, “Sue, Bobby’s here.”

Around half a minute later, Sue made her entrance down the stairs, and Bobby’s jaw hit the floor. Literally! He was standing there goggle-eyed with his mouth wide open. My sister looked outstanding! Mom had loaned her a dress, which while conservative for Mom, was a far cry from what Sue normally wore. It was a dark brown print, calf-length, with buttons from the hem to the waist up the front. About two-thirds were unbuttoned, showing her legs to several inches above the knee. Above the waist, it had a pair of wide straps which wrapped around to the back and were tied in a bow, letting a woman tighten it to give a very figure-flattering look. The neckline was quite broad and circular, showing a trace of cleavage, and almost all her shoulders. Mom had even loaned Sue a pair of low (for Mom!) two-inch-high heels. Sue had balked at makeup, but Mom had brushed out her hair, and she glowed in a wholesome manner. No doubt, she was a showstopper, and would be the belle of the ball.

Sue seemed delighted by the effect her appearance made and milked it for all it was worth, even twirling once at the foot of the stairs. “Well, how do I look?” she asked.

Reaching out, I tapped Bobby’s chin, and he closed his mouth. Coming out of his trance, he simply said, “Wow!” to which Mom and I laughed loudly.

“Offer the lady your arm, doofus,” I said. Bobby gave me a dirty look, but then smiled at Sue and cocked his arm out and she slipped her arm through with a grin. Then Mom gave Sue a kiss on the cheek, and we sent them out. As they went down the steps, I called out, “Now Bobby, make sure you pay lots of attention to your date tonight, because if you don’t, about twenty other guys will!” Both Mom and Sue laughed at that.

Mom and I stood in the doorway watching, Mom leaning against me, while I had an arm around her shoulder, as they got in his car and drove off. Finally, Mom looked up at me and laughed. “Well, Pa, our little girl is growing up.”

I laughed too as I closed the door, then followed Mom back upstairs. She went down the hall to her room and I followed, to see her picking dresses off her bed and putting them back on hangers. I leaned against the door.

“I’m surprised, Mom. There is no way she could wear a bra with that dress.”

Mom looked over at me but kept cleaning up. “Sure, she could, if it was a strapless bra.”

“Sue owns a strapless bra?” I asked incredulously.

Mom smiled and picked up a pair of scissors. “She does now.”

I laughed. “You couldn’t lend her one of yours?”

“Paul, we’re not quite the same size, yet, although if she keeps growing up, I suppose we will be someday soon. I guess I’ll have to take her out and teach her about lingerie soon.”

“Buy her some new underwear, huh?”

“It’s not quite the same thing, Paul.”

“So, what’s the difference.” {Tell me. Show me.}I was starting to get fairly turned on by where this conversation was going. Let’s see where it could take us.

Mom hung the last dress in her closet and turned to face me. “Well, underwear you wear for yourself, lingerie you wear for someone else.”

“Oh?”

“Uh, huh.” She held up one of Sue’s plain white bras. “This is underwear.” Dropping the bra on the bed, she grabbed the hem of her blue tank top. “And this is lingerie.” She whisked the tank top over her head and stood facing me in a small blue underwired brassiere. It was cut exceedingly low and was so transparent her nipples were visible through it. The overall effect was to lift her full breasts and present them for viewing (or whatever!) as if on a platter.

“That’s very interesting,” I said. “Does that come with a counterpart?” I asked, as my gaze dropped down past her narrow waist and deep belly button to her cut-off shorts.

In response Mom simply undid her waist button on the shorts and lowered the zipper. Pushing them down off her hips, she let them slide down her legs and stepped out of them. Her panties were part of a matching set, blue, quite small, and very transparent, although they seemed opaque enough to hide her pubic bush, which I couldn’t see. “See, this is not what you could call underwear,” she said. “Now, get out of here while I get dressed.”

I straightened up without taking my eyes off her. “Don’t change on my account. I like seeing beautiful women running around in their unmentionables.”

Mom smiled at the compliment. “Shoo.”

As I turned and left, I smiled back. Silently I used The Power to tell her that I liked seeing her in lingerie, and that she should wear it often in my presence.

By mid-December, I was stuck at home. Sue was at a girlfriend’s house for a combination birthday party-sleepover and Mom was on a date. I was dateless again, for the simple reason that Jenny and I had broken up. I had not used The Power to force her to be with me, only to make her my girlfriend. Well, boyfriends and girlfriends usually break up at some point, and so had we. In truth, Jenny had always had a bit of a roving eye and had begun flirting with a senior. And for my part, I had been dabbling on the side anyway.

My dalliances were at the gym where I worked out three times a week. I was no longer in therapy, but it was recommended that I continue to exercise, so I had joined a health club. On my third visit, I had noticed a good-looking middle-aged woman, forty or so, watching my progress closely, as if she was interested in me. As she passed by me, which she did several times, I sent out a thought, {Answer me. Like what you see?}

“Yes,” she verbalized.

{Let’s get acquainted.}”Hi, I’m Paul Harron,” I said.

The lady stuck out her hand, “Sherry Lanst. How do you do?”

{If you want me, let’s go somewhere and get it on.}

Sherry had a puzzled look on her face for a moment, as if she was coming to a decision. Then she came closer to me and lowered her voice. “Paul, don’t be offended, but I find you very arousing. Would you like to come over to my place for coffee, or whatever?” she asked.

Wow, talk about arousing! My dick, bent over inside my jock strap, tried unsuccessfully to rip through my shorts! “Sherry, I am not in the least offended. Why don’t we clean up and I’ll meet you in the lobby in fifteen minutes?” We separated, whereupon I took the fastest shower in history, during the longest fifteen minutes of my life. Truth be told, we got to the lobby within a minute of each other.

“Follow me in your car. I live about ten minutes from here,” she said.

Sherry lived in a suburb on the west side of town, and it was easy enough to follow behind her. I parked on the street and went up the walk to the door which she had left slightly open. I pushed it open and went in, closing it behind me. The first thing I noticed was her sweater, which was laying on the floor where she had thrown it.

“I’m up here.” She called out.

I picked up the sweater and went upstairs, picking up a T-shirt and a bra that I found on the stairs and in the hallway. As I entered her bedroom, I saw that she was sitting on the bed, kicking off her shoes and tugging off her jeans. Standing, she pushed them and her panties together down her legs. Naked she lounged back on her bed and said, “Well, don’t just stand there, get undressed.” I got undressed. We never took our eyes off each other. My cock was fully erect by the time I had my briefs off.

Sherry may have been older than my mother, but she was still a fine-looking woman. A medium-height, medium-build bottle blonde, she had nice legs, firm breasts, a slim waist, and a triangularly trimmed brown bush. With much anticipation, I crawled onto the bed and stretched out next to her.

We immediately began to kiss and stroke each other’s sides. As soon as I begin to fondle her breasts, she reached between us to stroke my cockshaft, whereupon I promptly moved a hand down to her crotch to finger her clit, while licking and sucking the breast I had abandoned. She was quite wet and began to jack on me so that I began to worry I was going to pop off in her hand when Sherry shuddered and came. Releasing me, she raised her arms above her head and reveled in the sensations emanating from her crotch. As she came down, she began to stroke me again, leaning in to lick my neck and upper chest. I lay there on my back, stroking her sides as she began to give me a hand job, then I lightly pressured her shoulders to tell her to move her head downstairs. Taking the hint, Sherry kissed and licked her way to my dick, which she gently took into her mouth.

Within a few minutes, my lady friend had a nice bobbing and sucking action going on in my groin, and I decided to return the favor. “Swing your ass up here. I think you need a mustache ride,” I said.

Sherry stopped her fellatio and looked up at me and giggled. “Really? What, sixty-nine?” she asked. I nodded and she repositioned herself, straddling my face and gently lowering her pussy to my lips. After my first few licks, she said, “God that feels good! My husband never wants to eat my pussy,” then lowered her own face back to my dick. Husband? Oh, well, hopefully he wouldn’t come home any time soon, and if he did, I would have to use The Power to make him forget.

Sherry’s hubby may not have liked giving head, but I suspected he enjoyed getting it, because Sherry was fairly talented. He was probably also smaller than me, since she never took more than about half my length in, but boy that half got a real treat. Her tongue was doing a dance all over my cockhead, while she continued to bob up and down, all the while with the suction of a vacuum cleaner. It was all I could do to concentrate on licking her clitoris, and much too soon I cried out, “Oh, God, I’m cumming!” Sherry simply stopped bobbing, leaving the tip of my cock in her mouth and she sucked and swallowed my cum.

Untangling ourselves, Sherry stretched out by my side again, gently fondling my flaccid penis and kissed me. I could taste myself on her lips, a not unpleasant taste, but one which gave me a somewhat homophobic feeling, nonetheless. We talked while she fondled me to hardness once again. Her only daughter was away at college and Frank, her husband, was out of town on a business trip, so nobody would disturb our interlude. We could fuck as long as we wanted. They both had frequent little affairs.

As soon as I was rigid again, Sherry climbed atop me and sank down on my manhood. Not too tight, not too loose, just right! I placed my hands on her hips to gently guide her motions as she began to slowly bounce on my cock. For her part, Sherry began to pinch and twist her pert little pink nipples. As I brought my thumbs around to her front to rub her clitoris, Sherry began to moan with pleasure. Her shudders got us both off a little too soon, and she stretched out on top of me, with my cock inside her, and nuzzled.

For our next act, Sherry got on her knees, and I positioned myself behind her for a nice doggy-style fuck. I had sunk into the hilt, and we were bucking against each other quite spiritedly when we separated just a bit too much and my dick popped out of her cunt. On the in-stroke, my cockhead butted against her asshole.

“Wait, honey,” she said. She scrambled over to her nightstand and pulled a drawer open. Reaching in, she pulled out a small tube and handed it to me. “Use this first, please.” Sherry moved back into position, spreading her legs wide and lowering her face to the covers, raising her ass even higher in the air.

The tube was KY jelly; Sherry mistook our movements for an initiation of anal sex! Well, I was game, if ignorant. “Uh, you sure? I’ve never...,” I said.

Sherry looked back over her shoulder at me with a big smile. “Really? Frank and I just love to assfuck. It’s just so naughty!” She led me through the basics, squirting some out onto her anus, gently poking some up her asshole with a finger, and spreading some more on my cock. When we were prepared, she leaned back down to the bed and relaxed her ass. “Now, just put the tip in and give me a chance to get used to it. Don’t rush. Once it’s in, I’ll open up some more and then we can fuck our brains out. Just go slow and things will be just fine.”

“Okay, you’re the expert.”

It took me a good minute to force my cockhead into the little brown pucker and I damn near pulled out when she gave a semi-pained grunt on my entrance. “Okay,” she said through gritted teeth, “now slowly start sliding it in deeper.”

I began to carefully comply, both concerned for her and in awe of the intense tightness of her ass. “Are you all right?” I asked.

Sherry let out a long breath as I sank home. “Oh, God, yeah. It’s just that you’re so much bigger than Frank. I’ve never had a bigger dick in my ass. Oh, it feels so good. Now, fuck me, fuck me!”

Well, you don’t have to hit me with a rock to get me to go along. She wanted it, she got it! I slowly pulled my dick backwards until only the tip was still inside, then pushed it back in until my balls were swinging against her pussy lips. Sherry moaned in appreciation, so I repeated the procedure at a faster pace. Good Lord, she felt good. I stared down at the little brown ring, stretched to seeming bursting around my erection, and reveled in the sensation traveling the length of my cock. This was simply fantastic! I shoved back in faster, and Sherry had her first anal orgasm of our session, crying out in ecstasy. She came twice more before I couldn’t stand the pleasure and grunted loudly, collapsing onto her back as my cock twitched and spasmed, my balls pumping a major load of cum into her entrails.

Once we came down off our high and disentangled, I realized I had given her a load in every orifice, and I was fairly wiped out. I needed to get home. Looking down at my shit-stained dick I was mildly revolted and asked to use the shower. Sherry sleepily nodded and stretched out on the bed. Gathering my clothes, I retreated to her bathroom for a good shower.