School Crossing Guard

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The school crossing guard is his sexual fantasy.
3.9k words
4.31
46.1k
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3

Part 1 of the 2 part series

Updated 10/30/2022
Created 04/30/2007
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I saw her every morning when walking my kids to school. She was always there helping us across the street. She was no beauty just your average female school crossing guard. There was nothing special about her, that is, until she smiled. Once she smiled was when you saw that there was undiscovered potential of a pretty woman beneath her uniform.

Friendly and outgoing, she smiled a lot. She enjoyed her job, obviously, knew all the kids by name and they all knew her. During her brief time with the children, in the morning on their way to school and in the afternoon on their way home, she was an extension of their mothers fretting over them, buttoning coats, tying shoes, giving them verbal comfort, and making sure that they arrived to school and returned home safely. You could tell that the kids liked her because she made them smile with her smile and with her concern for their safety and well being. Actually, she made a lot of people smile. People going by her in their cars tooted their horns and waved.

"Where's your hat, today, Simon, it's too cold to be walking to school without your hat?" I heard her say to one of the kids yesterday.

"I forgot it," said the boy putting his head down.

"Good morning, Julie. Wait there and I'll be over to cross you."

"Okay."

She had short blonde hair, was maybe 5'4" tall, and weighed about 120 pounds. Everything about her appeared average, yet, every morning, I was excited with the anticipation of seeing her, again. Maybe, it is because I am horny in the morning and since my wife died a few months ago, there's been no way for me to release the sexual tension that controls my thoughts other than to masturbate. Like brushing my teeth, combing my hair, and taking my vitamin, masturbation has become a morning ritual since Amanda died.

Yet, masturbation is not nearly the same as touching, feeling, caressing, and kissing a naked and willing lover lying beside you in bed. Certainly, it is not nearly the same as making love. There are no fireworks when I jerk off. I am so very detached and it is all so mechanical. Not once, do I say to myself, gee, I can't wait to go home and jerk off; I am so excited by the thoughts of it. Okay, I may have said that when I was a horny teenager and my hormones were raging, but not now that I am an adult and have the ability to begin and sustain a sexual relationship with a woman but, it is too soon since Amanda died. I am not ready to start over, again. I cannot even imagine myself with another woman.

I grieve the terrible and sudden loss of Amanda killed by a hit and run driver while out jogging, as she crossed the intersection. Not only did he hit her but he dragged her body down the street a few hundred yards. The forensic report read, by the blue paint found beneath her fingernails, that she was desperately trying to hold on to the vehicle, so as not to be run over and may have survived the initial impact, but when she lost her grip and fell back on the pavement, the asshole ran over her head.

The severe injuries mandated a closed coffin. I identified her body and she was unrecognizable but for her few bloodied clothes that they found scattered along the pavement. They closed the street so that the police could pick up pieces of her before the morning traffic flattened her in the pavement like animal road kill. By the evidence left at the scene, a broken headlight and blue paint chips on her clothes, and beneath her fingernails, they narrowed the driver's vehicle to a blue, Chevy pickup truck. I wish I could find that bastard. I would kill him with my bare hands torturing him first to make him beg me to end his miserable and cowardly life. She was my dream woman come true and I am such a mess without her and my children are forever pained with the loss of their mother.

I miss feeling Amanda's tits pressed against my back when we spooned just before waking up. She always leaned into me, kissed my ear, and reached her arm over and down my body to put her hand around my cock. Instantly, she gave me an erection and I reached my arm over her and my hand back behind her feeling her firm, round ass. She had a wonderful ass. All of that jogging paid off. With my head on her breast, I miss having my hand resting on her flat stomach before she left to jog around the neighborhood. I miss her returning home flushed and sweaty and ready to take me deep inside of her in bed, on the bedroom carpet, or in the shower before getting the kids off to school. I miss her. I hurt missing her.

"Good morning, Baby, did you sleep well?" Every morning she asked me that simple, yet, endearing question. I never realized how important her concern for my good night's sleep was until she was no longer there to ask me that. I miss her and I miss her asking me if I slept well. She was my baby and I loved her.

Now, for some inexplicable reason, other than I am so lonely and so horny, the school crossing guard has garnered my attention and is my current fantasy. Whenever I think of the school crossing guard I feel like I am cheating on Amanda. We were together 7 years and I never cheated on her. Cheating on Amanda never even crossed my mind. We were so compatible physically, spiritually, and emotionally, that there was nothing that I needed that Amanda could not give me. Actually, except for the couple of women in work, the receptionist and the bookkeeper, the school crossing guard is the only other woman who I come in contact with on a daily basis and the only woman who I find myself thinking about.

She has a nice voice. She has helped me across the street so many times that her voice is a lyrical background in my mind. It is a melodious voice that is not too high or two low. It is a voice of a woman who is in control of her mood and her mood is always pleasant and confident. Her voice is feminine. I can see myself being aroused in bed by her voice when she is talking dirty to me.

"Freddie, I love holding your cock in my hand and staring at it just before I put it in my mouth. You have a beautiful cock. May I suck your cock, Freddie? May I take you in my mouth? Will you cum in my mouth for me? I love how your penis grows for me and how you tense your body just before you cum. I love the taste of you." (You can tell a guy wrote this.)

Jesus, I have to pay attention to my driving. I nearly rear ended the guy in front of me thinking about the school crossing guard talking dirty to me while about to give me a blow job. Oh, my God, I am so fucked up. What is wrong with me having sexual thoughts for my children's school crossing guard?

"What are the charges, Officer?"

"He's been stalking the crossing guard, your Honor."

That imagined exchange of dialogue that happened yesterday when picking up my kids from school made me wonder if she was married or attached. Most school crossing guards are married to or have a boyfriend who is a cop, which is how they have the inside information and preferred status to get the job, as a school crossing guard, in the first place. You would not think that a school crossing guard job was a plum position in the community but, it is a job that pays more than double the minimum wage and the extra income with mother's hours and within walking distance of their home, it is a job that does not interfere with the rest of their day. Suddenly, I felt like a cad lusting over someone else's wife or girlfriend. I would not like it certainly, if some Dude had been lusting over Amanda, although, I am sure there were plenty of guys lusting over her because she was a good looking woman who had a killer body.

Still, I wondered what she looked like without her orange safety vest. The cap she wore made her look cute. Some women cannot wear hats, but the school crossing guard looked sexy with her cap. I imagined her giving me a blow job while wearing her cap tilted to one side. Maybe, it was her uniform, maybe, it was because I was so lonely, so horny but, she was beginning to look hot to me.

I imagined her slowly stripping off her uniform, unbuttoning her blouse and unbuckling and unzipping her trousers to reveal an outrageous Victoria's Secret matching bra and panty set. You know the lingerie I mean, the one with those low cut bras that barely covers her areolas and that serves up and offers her tits to you and the one that has those panties that frame and highlight her mound. Oh, baby, I just love Vicky's dirty little secret underwear. You could be the most prim and proper every Sunday to church woman but still surreptitiously be wearing Victoria Secret underwear beneath your dowdy clothes.

So, there I was horny again before having to take the kids to school and jerking off in the bathroom while fantasizing about my school crossing guard. In an effort to add detail to my image of her while jerking off, I tried to think what color eyes she had. I figured blue but I was not sure. Were they blue, hazel or brown? She must have crossed me 100 times and I never noticed her eyes. I was probably too busy staring at the impression her tits made in her safety vest or how her round ass filled out her uniform pants. She was definitely a full B cup, maybe even a C cup. Even with her safety vest, I could tell she had tits, nice tits. It is difficult to tell with all the clothes she was wearing and navy blue made her appear thin, really thin, still, when I stared at her long enough, as I apparently have over the months, I could see that she had womanly curves that gave her a hot body.

I wondered what her name was. It bothered me that I did not even know her name. What a knucklehead I am. That missing detail ruined my jerk off session. How could I jerk off over someone without even knowing her name? Suddenly, I felt like Jerry Seinfeld when he forgot the name of his girlfriend, "Oh, you, you, you," he called her. "You are so pretty. You are so sweet." Jerking off about someone without even knowing their name is like trying to jerk off without touching yourself. I stuffed my limp cock back in my pants and went downstairs to hurry the kids for school.

Today, I would make eye contact with her to see the color of her eyes and today I would ask her name. I was nervous driving the few blocks to where I park my car to cross the kids. She was there stopping cars and crossing kids. I stared at her from a distance. Yeah, she has tits alright and a shapely ass, too. She wore white gloves. I imagined those white gloved fingers wrapped around my cock stroking me until I cam and shot loads or warm, oozy liquid all over her white gloved hand. Unable to jerk off this morning, still horny, seeing her made me want to fuck her and, seeing her dressed as a school crossing guard made me want to fuck her while she was still in her uniform and, while she was wearing those white gloves. Now, I understand the attraction that some women have with a man in uniform.

"What are you doing?"

"I'm taking off my hat, orange safety vest, and white gloves so that we can fuck."

"No, put everything back on, please."

"You don't want to have sex with me?"

"Yes, of course, I do, but I want you to wear your uniform while we are making love." I looked down embarrassed that my request may be deemed kinky or distasteful to her. "I want to feel your tits through the cloth of your orange safety vest before removing it. I want to feel what it is like when you wrap your hand around my cock while wearing your white gloves. I want you to suck my cock while you are wearing your hat."

Her dark blue pants and shirt covered over with an orange safety vest, her white gloves, and blue and black cap made her more appealing to me than all of the other mothers who marched their kids to school wearing their stay at home Mom uniforms of jeans, sweatshirt, and sneakers. There was something erotic and sexy about a woman in uniform albeit, a school crossing guard's uniform. Some professions because of stereotypes are erotic and when having sex with someone of that profession some guys feel that a nurse will make them feel better, a librarian will teach them to be quiet, a secretary will remember their moves, a teacher will make them stay after and do it over again, or a nun who will forgive their sins. For me, it was the school crossing guard that made my cock hard. For me, it was the school crossing guard who will make me stop, look, and listen, as she takes me by the hand to cross me over to the other side.

"Hi," I said to her as she approached to cross us. She has pretty blue eyes. I thought she did.

"Hi," she said, "how are you, today?" She maintained eye contact with me and smiled that smile that lit up her face making her look so much prettier than when she did not smile, which was rare because she was always smiling.

"Good, how are you?" I said walking with her as we crossed. Suddenly, I had the urge to take her hand and hold it while crossing the street. Suddenly, I had the urge to relinquish all of my sexually control to her and to have her make love to me instead of me making love to her. Please walk home with me I wanted to say to her.

"It's a nice day so far, although there is rain in the forecast."

"I'm David, Ashleigh's and Stephen's father." Fuck the small talk. Can I fuck you? I wanted to ask her the really big questions. Would you walk me home so that we can have hot sex? May I strip you naked and make love to your hot body for hours? Are you married? Do you have a boyfriend? Instead, of asking her all the questions that filled my mind, I made small talk.

"I know who you are," she laughed. "I cross you every day since your wife..."

"You knew Amanda?" Suddenly, the guilt welled up and I felt bad like I was cheating on Amanda.

"We were acquaintances," she paused. "We talked sometimes while waiting for the kids to get out of school." She looked up at me and touched my arm with her white gloved hand. "She was a nice woman. I am so sorry for your loss."

"Thank you," I said waiting for the uncomfortable pause to pass. "What is your name?"

"Dorothy" she smiled, "but everyone calls me Dot." She laughed. "It was a nickname that stuck with me from high school because I was smaller than all the other kids, until I grew finally," she said depositing us at the curb and getting ready to walk back to cross a couple of kids waiting impatiently to cross.

"Well, I have the get the kids to school before they are late."

"It was nice meeting you, officially, Dot." I stuck out my hand and she took it in hers. I held it feeling her fingers encased within her white gloves before shaking it. I got chills thinking of her white gloves touching my naked body. I started getting an erection thinking of her hand gloved in white cotton holding and stroking my cock.

"Nice to meet you, officially, David," she said smiling.

I was running late the next morning and got the kids to school late. I did not get my daily dose of Dot. With the other kids already in school, she was gone. Not seeing the school crossing guard put me in a bad mood. I was depressed. I was lonely. I was horny. It was raining. She was my only female companionship, if you wanted to call her that. I was in a sad condition. I looked forward to seeing Dot when I picked up the kids but, again, she was not there.

"Where's Dot?" I asked the substitute school crossing guard.

"Car problems," she said with a shrug. "She called me asking me to fill in for her. She said that she was broken down at Home Depot."

I needed some time alone so when I picked up the kids at school I dropped them off at my sister's house and drove to the mall to roam around...Home Depot. Although I was hoping, I really never expected to see Dot. I figured she'd be long gone after getting her car started or getting a tow. Besides, what if she really wasn't stuck and just called her friend and made up an excuse not to go in to work?

I pulled in a parking space closest to the door. It was pouring buckets. The pickup truck next to me had its hood open, which I thought was odd considering how hard it was raining. That was when I saw her standing at the front of the truck. At first, I did not recognize her. She looked different, better, without her uniform. She looked pretty. Her hair was pulled back and she wore makeup.

"Hi."

"Hi, she said, "can you give me a jump? I think my battery is dead, at least, I hope it is the battery and not the alternator."

"Sure." I grabbed my cables and jump started her. It was her battery.

Suddenly, I got this feeling that I have not had since high school. My palms were sweaty and I had butterflies in my stomach.

"Uhm," I said, standing in the rain beside her truck and talking to her through her window that was open half way. "You wanna get some coffee?"

She looked at me and I looked back at her. In a flash of enlightenment, her face mirrored my loneliness and her expectations of hope for the start of something good. The look that appeared upon her face only lasted but a second but it seemed like forever before she responded to my question.

"Sure," she said, giving me that smile, "I would love some coffee." She wrapped her arms around herself pushing her ample breast together revealing a deep line of cleavage above her shirt. "I'm chilled to the bone."

"There's a Starbucks up the road." I gave her another look and was happy, thrilled with the prospect of having coffee and conversation with the woman in my fantasy. "You can follow me."

"Okay."

We headed up the road and parked beside one another in the parking lot. She grabbed a table while I ordered a couple of coffees. It was all very innocent, just coffee and conversation, although I was hoping for more and if I read the look on her face correctly, she was hoping for more, too. That was how it started.

She told me that she was recently divorced, had no kids, and was lonely. We ended up at her apartment. With the rain hitting the windows and the misty fog that reflected the light back in the room, it was all so surreal, like a dream that I had dreamt before. Somehow, our first time together felt like it was all pre-planned and I was a pawn going through the choreographed motions of making love to this woman who I hardly knew. Somehow, I felt manipulated.

By her moans and sexual aggressiveness, she wanted the sexual contact more than I did. She was hot for me, certainly, that was obvious. Whereas, I wanted to fuck her, she wanted to make love to me. She engulfed my cock, deep throated me, and I nearly lost it and exploded in her mouth. The only reason why I did not, why I was able to hold back was that I needed to fuck. Yet, I, too, needed the comfort of her body. I missed making love with Amanda so much that I needed to feel the wet, warm tightness of a woman.

Still, by the passion behind her kisses, she wanted me more than I wanted her and I was taken back by her forwardness. She was not shy about how she felt about me. She was not cautious and holding back her affection. Accustomed to a first encounter that was more guarded, I not only felt her reaction refreshing to my conditioned opinion of women on first dates and but, also, flattering to my ego.

She was a great kisser. She made my cock hard just with her kisses. I have never kissed a woman as much. My lips were sore but I did not care. I did not want to stop kissing her. Maybe, it was her full lips, Amanda had thin lips, but Dot was the best kisser that I have ever experienced. I felt connected to her through her kisses and I could not get enough of her tongue. She made me forget everything but kissing her.

We made love, first, and then, we fucked. We fucked like dogs. By my measure, I could tell that it had been a while for her, as it had been a while for me, since having sex. She was so wet. When I tasted her, her wet sweetness covered my face. I made her cum hard. Then, I searched the room for something to wipe my face. She was on my cheeks, chin, and up my nose.

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