(For a woman with a great Heart)
Janet Penniwell wasn’t the first girl I had fallen in love with, nor second or third. Heck there was a time in my teenage years where falling in love was a weekly occurrence, not that any of the girls I had fallen in love with had a simple clue.
Falling in love was easier than being in love, and these relationships were purely in my mind. Girls from school were on the list, but the truth be know I was most infatuated with movie stars and celebrities of many walks of life.
My biggest crushes were with my ninth grade English teacher, Mrs. Vance (oh, I wanted to get into her pants) and the local female television anchor, the one with bright blue eyes and an infectious smile.
All were unattainable for one reason or another, but all were featured in my vivid imagination being loose and attracted to, well, me.
My first kiss came at the junior prom, but it wasn’t until my senior year that I wasn’t stopped with a peck on the cheek or, with a couple girls, passionate kisses (with tongue!). That senior year saw me dating a darling girl, the aforementioned Janet, and we had wonderful times together. Long walks in the park, dinner and a movie, even days at the beach. At a graduation party she young brunette allowed my hands to travel under her bra for the first time. The touch was fantastic, and I longed for the night when I would finally convince her to give into my passionate demands for more.
Janet, though, held back. She insisted no sex meant no sex, and it frustrated me to no end. I would beg and plead but had to be satisfied by heavy necking sessions which included kissing, nibbling and sucking on her bare breasts but no more.
After one fun yet unsatisfying date I walked her up to her front door and begged her to reconsider, pledging love forever and anything else imaginable, but she shooed me away and told me to be strong.
The next afternoon I arrived at the Penniwell household in the afternoon for what was supposed to be a swim with my girlfriend, only to be greeted by her mother who explained Janet was able to get a last minute tennis lesson with the lead instructor and had just left the house. She apologized for her daughter, but said it didn’t make sense for me not to get my swim so the pool was open.
The heat was intense and the pool sounded inviting so I agreed and thanked Janet’s mom for the opportunity. Minutes later I was doing laps before settling into an inner tube to relax when Mr. Penniwell came out and asked if I minded if she join me in the pool.
While saying it wasn’t a problem I began to stammer, as Mrs. Penniwell dropped her cover-up on a chair. It was a picture of perfection. The 40ish woman stood for a moment before me in her miniscule pink string bikini, a swimsuit which left little to the imagination. She had to have C cups, a wealth of cleavage, and while she wasn’t thin she wasn’t bulging out in any strange places either. I mean, it was a woman’s body in a tight, tiny swimsuit.
I was startled by the sight of her skimpy covered body, I know I did a double take as the woman seemed oblivious to my staring eyes. She was a beautiful angel of a mermaid slipping into the cool waters of the pool for her laps. Watching her swim, I though of a goddess. She looked awesome, no doubt about it. And my cock stirred in my bathing suit as I captured glimpses of her barely covered breasts or tight buns.
As if in a trance I merely watched her swim. Never had I imagined my girlfriend’s mom could be so beautiful.
Mr. Penniwell emerged from her workout, grabbed a towel, and looked teasingly over her shoulder at me.
“Well, Jonathan, are you done staring? Did you enjoy the view? That’s not polite, you know,” said the woman as I stuttered and stammered some meaningless answer.
What could I say? She was my girlfriend’s mom and I was looking at her as if she were a prime cheerleader swaying at the football game.
She sat back in the pool chair and laughed. “It’s okay, boys will be boys, if only my husband looked at me that way….well, it’s an honor young guy like you took notice of me.”
Mrs. Penniwell sat back as I attempted to take the stupid look off my face. I know guys talked at school about other mom’s, MILFs, but I never imagined I would be face to face talking, well, intimately with one. I was embarrassed at being caught staring at her, but then, she was indeed beautiful.
We made small talk for a while. She asked my summer plans, I asked what project she was working on these days. My girlfriend’s mom was always working on some
“Jon, can I speak with you about something personal?” asked the woman as I nodded yes. “You and Janet, well, I know you aren’t going all the way, but I am concerned you are pressuring her a little too much, she’s just not ready for that yet.”
I told the blushing mom that I had no intention of doing anything Janet didn’t want, I wasn’t that kind of guy.
“Bullshit,” said the woman, sternly, nearly knocking me off the tube and into the pool with her voice. “I was sitting on the porch last night and I heard you two talking. That sounded like you were pleading, begging, and I had to laugh. On one hand I was proud of my daughter, but on the other I was disappointed in you. I didn’t think you were that kind of boy.”
My mind jumbled, listening to my girlfriend’s mom lecture me. “Oh, what can I expect? You’re 18, you’re a man, and I bet you are preoccupied by sex? I bet she sent you home last night with, what do you guys call it, blue balls?”
My ears couldn’t believe the sound coming from Mrs. Penniwell’s mouth. I mean, never had I heard such, well frank language, not even from my health teacher. She was right, of course, I wanted to bang her daughter, and yet I couldn’t admit to it for fear of the consequences.
We sat in silence, she on the chair, me in the pool, for several minutes before Mrs. Penniwell spoke. “It’s okay, Jon, no more lecture. You know how I feel and I better not catch you going to far with Janet. Neither Mr. Penniwell or I will not stand for anything, or anyone, getting in the way of her college education.”
I nodded and mumbled something about of course I would respect and keep my hands to myself. Of course while I was saying this I had a perfect view of Mrs. Penniwell’s shapely thighs and my eyes wandered right up toward the V in her bikini, a fact that was obvious after only a few seconds.
“You are such a bad boy, Jon…okay, I give up, grab a Coke and join me up here, I need some lotion on my back.”
I started out of the pool before realizing I had a hard on leading the way. Stopping in my tracks, I couldn’t get it to go down. “What is it, Jon, what are you waiting for?….oh!”
The woman caught on to my predicament. “I’ll turn over, Jon, uh, you and you problem can get that drink.”
I tuck myself in as best as possible and thought of scary things and before long the bulge was only small. Sitting to her right, I grabbed the lotion and coated her back before sitting deep into the chair.
“So, does she give you blue balls?” Janet’s mom surprised me several minutes later.
“What do you do about it?”
I couldn’t believe the conversation, but she was a mom and all good and I didn’t want to stop the conversation.
“I take care of myself when I get home,” I admitted, then followed with the admission that I did that several nights a week thinking about not only her daughter but others.
It was as if we were in a parallel universe, as if I was in confession and she was going to give me approval or forgiveness or something. I spilled out details of how I’d masturbate, how often I’d fantasize and about whom, you name it. I admitted I was a virgin, had never gotten to third base, and how some of my friends had.
“It can be wonderful, Jon, but you are too young, wait for a while, savor the experience of experimenting, of the chase, of the anticipation. It’s something you will never forget.”
Mrs. Penniwell turned over and looked me squarely in the eyes. “Can I ask you something personal?”
I nodded yes.
“How big is your cock?”
I stuttered and stammered once again. This woman asked questions that women weren’t supposed to ask. Wondering if it was a test, and whether she’s suddenly slap me, I merely stared.
“Just asking, Jon, you don’t have to answer. But I have to tell you I am a little concerned about you and Janet, and I really think you have been pressuring her a little too much. She’s not ready for sex.” With that she got up, put on her flowing white cotton robe and strode into the house leaving me confused as to what to do next. Was I supposed to leave? Wait for Janet? Swim?
Mrs. Penniwell answered the question a minute later when she emerged from the house. “Janet called and will be home in a little more than an hour,” said the pretty mom. At this point I noticed something in her hand, a ruler.
“Come here, Jon, if you are dating my daughter and can’t keep your hands to yourself I have to remind you that it is not gentlemanly to constantly hit on her.”
She took my hand and marched me into the basement. She led me to a large wooden desk. “Bend over the desk,” she sternly commanded in no uncertain terms.
At first I thought she was joking, but the look in her eyes was anything but in jest. A myriad of thoughts exploded through my head, everything from this woman is a crackpot to if I don’t do what she says it might affect my relationship with her daughter.
She pushed me down and told me to lower my swim suit. I couldn’t help but follow her insistent instructions, and I slowly slipped the trunks down my backside, baring my ass.
“That’s better!” said the woman, resting the ruler on my bare ass. Then name one, two and three rifle quick smacks followed by a loud “ouch” emitted from my lips. Spanks four, five and six were firm, but the last four were stinging blows.
“Next time you are petting with my daughter your hands better not be roaming where they shouldn’t be,” said Janet’s mother as she lifted my up off the desktop. “Oh, what have we here?”
Here was my cock, standing at full erection. Why, I have no idea. But while my ass burned my dick churned, a mind of its own. Through tear-stained eyes I slowly lifted my gaze to Mrs. Penniwell. “I, well, I’m sorry, mam. I didn’t mean to….”
She shook her head then smiled.
“You are such a guy, Jonathan. Here’s I’m attempting to correct you, to punish you, and what do I get? You cock at attention.” The woman continued to smile, then, eureka, came up with an idea. “Well, since I have the ruler and you,” she nodded at my midsection, “have that, let’s check it out.”
In a flash Janet’s mom had the base of the ruler against the base of my cock, and she was holding it steady against the wooden ruler.
“A little over six inches,” she surmised. “Six and a quarter.”
Until this point I hadn’t realize she was holding my dick, but when she did the measurement I glanced down and realized where my manhood rested. That sent my dick throbbing around as my mind realized I was being touched by a female for the first time.
Mrs. Penniwell went over to the couch and sat down, patting the seat beside her. I shuffled over and sat next to her, embarrassed and on sore buns.
“Is that for me, or does it do that for any female,” said the woman.
“Uh, I think it’s a combination of things but yea, you are the reason.”
With that she shook her head then reached over and slowly, tantalizingly, began stroking my dick.
“Mr. Penniwell, Herbert that is, has one curved cock just like yours. It’s a little longer, but yours is thicker,” said my girlfriend’s mom as my dick jumped in her hand. “He doesn’t give it to me as much as in the old days, especially not as much as when we were courting.”
I mumbled something about her being beautiful, and she continued to jerk my dick.
The woman sensuously stroked my rock hard teenage dick up and down, up and down, alternating those strokes with a few caresses of the base and then the tip. I was ready to explode and tried everything to delay, but soon my cock was spurting one, two, three shots of sticky fluid high in the air and all over her hand and arm.
“Wow you have a lot of stuff, I thought you said you masturbated this week?” said the woman whose stroking continued, milking every ounce of cum out of my spasming cock.
I merely groaned as my dick was doing the talking.
Savoring the moment I leaned back onto the couch, gasping for air. It had been an incredible hand job. But what happened next took whatever air I had out of my lungs. The woman leaned back, opened her robe, took my hand and inserted several fingers under the front of the bikini.
I couldn’t be sure of how much, but she clearly trimmed down there, and soon my fingers were walking the wet slit first on the outside and then inside her hot, gooey hole.
“Ooohhh, that’s it, don’t stop,” said the woman as I played with her middle-aged pussy. “That’s so good and so naughty. I can’t believe I’m doing this, we’re doing this. In the basement and while I am wearing my daughter’s swim suit.”
Wow, so that’s why the suit was so tight! She was wearing Janet’s swim suit. Of course, a mom wouldn’t own such a revealing outfit.
I continued to flick in and out of her pussy, bringing her higher and higher. Her eyes were closed, head tilted back, mouth opening and closing as her breathing quickened. It wasn’t long before she groaned and let out a little gasp as she came all over my fingers.
The look on her face was priceless, and I merely stared at it while slowing down my finger action.
Mrs. Penniwell leaned over, kissed me on the cheek, and noticed once again my growing dick. “Doesn’t that ever go down?”
She answered herself. “I guess not without help.” With that she bent over and took my cum-soaked cock between her lips. Words can’t describe the feeling of your first blow job, but suffice it to say my dick jumped, shook, rattled and rolled all over the pretty woman’s face, cheek and mouth.
The woman moaned as she sucked my hardened cock to full erection. The feeling of her licking and sucking was electric, my body shook as my girlfriend’s mom mouthed my cock with a wealth of experience. I couldn’t believe the way she sucked most of my cock into her mouth and then slowly drew her head up to the tip. There, she sucked on the end and then slowly licked circles around the mushroom shaped head.
The sensations were unbelievable. I had always wanted to have my dick sucked, but never had I imagined how absolutely wonderful it would feel. It was everything I could have imagined and more.
She made love to my cock. There’s no other way to put it. She sucked it, kissed it, caressed it. At one point she slowly started at the top, tightened her lips, and moved slowly down my manhood. She got most of my cock into her mouth, and what she didn’t was held and stroked by several fingers.
My girlfriend’s mom continued to bob her head on my dick and within minutes I was shooting a load of copious cum into her beckoning mouth. Surprising to me at the time was how she never took her mouth off the cock, swallowing every drop of the sticky stuff.
Well after my dick subsided in length I looked at the woman and mouthed a very quiet thank you.
She shyly smiled, and reminded me to keep my hands away from her daughter.
It was a reminder, reinforced by my girlfriend’s mom several times that summer, I took to heart. Janet was a wonderful girl, but her mom was an absolute cocksucking goddess.
Janet never caught on that her mom was taking care of business with lucky young me. I wasn’t telling.