Chapter 14

Okay, many of my readers are asking why Howie isn’t getting it on more often with his sister Stephie and her girlfriend Candy. I know, I know, it’s the heart of the story, but remember it’s a long story; and the events currently being written about take place in relatively short order.

For example, Howie gets it on with his mother—the girls fight over him and he’s sent home for a day. His Aunt Elaine arrives, and of course he gets it on with her and his Mom. He does call his sister and tell her what’s happening, and please bear in mind that he can’t up and leave for the city just because he wants too. He is a high school student after all. Moreover, he doesn’t want anyone finding out about his relationship with Stephie.

All of which brings us to another hurdle for Howie to surpass – And then I promise we’ll find a way to bring Howie and Stephie together again. I just ask for a little more patience on your part. Thank you -- PW

The next day I all but dragged myself to school, thankful that Reggie and Becky were still suspended and I wouldn’t have to contend with their sexual needs. I was also wondering how to tell my sister about my time with my mother and Aunt Elaine, or if I should, and then remembered that I had already mentioned the possibility of getting it on with Elaine and that Stephie already knew about mother and me.

A phone call was in order. It just wasn’t needed right away. Then again, Stephie would probably call me if I waited, and decided to do just that.

I was too tired to think it through anyway. Aunt Elaine and my mother had nearly drained me of sexual desire, or so I thought as I entered my homeroom and sat wearily at my assigned desk.

But as fate would have it, my mind began replaying some of the previous nights more erotic events, for example---and I’m keeping this short---my aunt had a favorite thing she taught me that, according to her, intensified her orgasm, and how could I refuse that?.

It involved holding her down---my mother stood guard lest I fuck things up---and squeezing Elaine’s throat, especially her windpipe, as we fucked. There was no question of it being anything but dangerous, but she steadfastly maintained it left her with incredible orgasms. In fact, she performed the feat on my mother while I stood by later on. In return, my aunt sucked my toes while my mother fellated my cock and that was something special too.

At school that morning, after my home room teacher, Mrs. Bloom took attendance, she read off that days special announcements and the bell rang for first period class.

As fate would have it, my class was in the same room with Mrs. Bloom in which she taught History of the U.S. Government. That left the two of us alone for a minute or so and she approached me as my memory of the previous nights debaucheries began to fade, leaving me with a monumental erection.

“Could you come up here and give me a hand, Howard?”

There was no avoiding it, I got up and walked to the front of the class where Mrs. Bloom was waiting. Now Mrs. Bloom was a very attractive 30 something blonde. She was especially attractive that day as I was noticing for the first time having emerged from my erotic reveries when she had called my name. She wore a white blouse and a black skirt that went down to her knees. The blouse had been buttoned all the way up to her neck during homeroom class, but now several more had been opened and a lacy white bra was now visible.

“So, I see you’re determined to live up to your new reputation, eh, Howard?”

I didn’t catch her meaning until she slowly pointed to my erection. “It is impressive. Does it ever go down?”

“Um, yeah, it does, Mrs. Bloom.” Since she was looking at my hardon, I took a chance and peeked into her blouse. All I could see was the top of her left breast, but it was a formidable top, promising much more impressive parts further down that lacy bra.

“I was thinking, Howard, if you might be interested in a special study course I give to promising students after school.”

“I’d like to hear more about that, Mrs. Bloom,” I said still glancing, but not furtively down her blouse since she hadn’t bothered to straighten up.

“Do you like them, Howard?”

“I do ... very much, Mrs. Bloom.”

“The other students will be pouring in any second, so why don’t you meet me at my house after school?”

“I can do that, Mrs. Bloom,” I said now looking her directly in the eye. We were no longer just teacher-student, but man and woman, and that was thoroughly understood by the two of us.

“Of course, you’ll need to demonstrate that you’re committed to seeing this out.”

“I can be very committed, Mrs. Bloom, really, I can.”

“So I understand. Well then, 3940 West Bend Avenue. It’s a pink house. You can’t Mrs. it.”

“Three-thirty a good time?” I asked.

“Perfect. We should be finished around five, unless you can stay longer.”

“Why don’t we play that by ear, Mrs. Bloom?” I said as two girls entered the classroom and took their seats. I turned away from Mrs. Bloom and took my seat as well. On turning back to face the front of the class I saw that the buttons had miraculously been buttoned again. Nothing left to peek at ... for the time being.

The rest of the school day flew by, well almost.

Sydnie-Ann cornered me during my lunch wanting to know if we could get it on later that afternoon. She looked good and smelled even better. I allowed my hand to wander up her leg and under her skirt, stopping at mid-thigh. Then I just caressed her warm flesh and enjoyed feeling her tremble with pleasure at my touch.

“I’d like nothing more, Sydnie-Ann, but I’, on a strict curfew at home. My mother has everything timed. It takes, according to her, twelve minutes to go from school to my house. Actually it takes sixteen minutes, but she’s set time limits on me. So as much as I want to ... I mean, look at me...” I gestured toward my groin and the ever present bulge there.

“Can ... Can you finger me? I’ll cum quick. I know I will!”

I shrugged and sent my hand to her crotch. She was soaked. Curling my fingers I eased them under the elastic band of her panties and within seconds found her opening.

“Oh Christ!” she moaned as they slipped inside. Once I did, I wished I had more time to savor the moment, but we were both already in a compromising position. No need to make the moment last forever.

Looking back up at Sydnie-Ann, I caught her staring down at where my fingers had disappeared under her skirt. She made absolutely no attempt to stop me and there was no look of fear or shock on her face. She did stop breathing as she waited for my finger to plunge further into her.

Then she let loose a breath and immediately took another one in while closing her eyes when my fingers began to pump in and out. I felt her pussy swallow my fingers within her surprisingly tight and very wet vagina.

“Fuck...” she whispered under her breath. A hand fell to my wrist, but she applied no pressure as if to push me away. Instead, she let her hand rest there as if to hold onto me more than anything. In our quiet classroom, the wet and squishy sounds of her cunt grew as I withdrew my index finger and pushed back in.

“Oh, shit.” She closed her eyes for only a second before again opening them wide to keep an eye on the door. “I shouldn’t...”

Well I knew damn well I shouldn’t, with all the risks involved, but I did, and that made everything hotter.

I studied Sydnie-Ann’s face to give me a clue and when my thumb rolled over a familiar little bud, her body convulsed and I knew I had found her clit.

“Oh ... fuck ... you should stop...”

Only she didn’t want me to stop in any sense of the word. She was pressing down on my hand keeping it in place.

“You don’t want me to,” I replied, stating the obvious.

She turned to find my eyes. “No ... I don’t ... oh, yes ... right there, Howie...”

I rubbed at her clit, and getting bolder, slipped my middle finger inside of her to join the index. It was a tight fit, but her reaction told me that I was doing exactly what she needed.

“I can’t ... I can’t believe we’re doing this,” she whispered. Her grip on my arm grew more and more urgent as if my fingers and arm were becoming more and more a part of her and they couldn’t leave. Her moans although quiet, were growing louder, and the smell of her pussy was becoming all the more evident and turning me on even more.

“You gonna suck my dick, Sydnie-Ann?”

“YEAH!”

“Gonna lick my balls?”

“Oh, YEAH!”

My cock was leaking precum like Johnny B. Goode. I wanted to taste her, but that wasn’t feasible. In fact, we had only seconds left to us before someone would walk in on us.

“Oh, fuck, so fucking close ... keep doing that...”

“Cum for me, Sydnie-Ann. Cum for me you little slut!”

“I love ... Uh-huh ... that you still call me that, Howie!”

I was rubbing her clit as fast as possible under the circumstances.

“Oh ... oh ... God!”

Sydnie-Ann gripped my arm so hard I groaned. She closed her eyes and rode out her orgasm as she tried to stay as quiet as possible. It would have been comical if it wasn’t so sexy. Her breathing was erratic and a high-pitched squeal was impossible for her to keep in as she hit the crescendo of her orgasm. Her mouth opened, but no sound came from it. I badly wanted to kiss her, but even if it would have been difficult to explain the position we were in, it would have been impossible to explain me kissing her.

As the seconds ticked away and the orgasm finally became less strong, she applied lighter pressure to my arm. Instead of holding it to her, she pulled it away. Her eyes pleaded with me to allow her to do so. I did and my fingers slid from her depths.

“Too ... too sensitive...” she whispered breathlessly, explaining why I had to stop touching her.

My fingers were soaked with her juices while my thumb was also damp. I placed my hand in front of my face and smelled her pussy. It was a strong odor and a sexy one at that. Waiting until she finally opened her blue eyes to look at me, I took one of my fingers into my mouth and sucked it clean. She stared surprisingly at me for a second before smiling. I did the same with my other finger and she continued to smile towards me. I would have sucked my thumb clean as well, but she moved to grab my wrist and brought the hand to her. My dick was trying to tear through my pants to get at her and she saw the bulge and laughed.

“I’ll suck it and fuck it after school, if you want, Howie.”

“I’d love that, Sydnie-Ann, but like I said, I’m being timed. If I don’t want to be grounded after this week-end I’d better heed the time limits.”

“Then anytime, anyplace, Howie. That was a terrific cum you gave me and I really needed one.” Then she gave me a quick kiss on the lips and wrapped her sweater around her skirt. “So no one sees the wet spots you left me with,” she laughed and vanished through the door as four girls rushed into the classroom.

I arrived at Mrs. Bloom’s House at approximately 3:30 and checked my hair in the reflection of her front door before ringing the bell. I was still naive enough not to consider the possibility of her husband answering the door when I rang the bell. Fortunately he didn’t, she did, and did so wearing considerably less than I’d ever seen her in, or expected for answering the door.

The robe she wore was almost transparent. White in color, and she seemed very tired.

“Hello Howard,” she said in a husky voice that smelled of bourbon. So, she wasn’t tired, I realized. With a deep sigh, she stepped back, and allowed me to enter her living room. When I turned to face her she was undoing the ties that held the robe closed and let it fall open. I drew in my breath. It wasn’t so much her full, pendulous breasts as the fact that the woman was entirely devoid of body hair. Glancing down at herself, Mrs. Bloom said in a tremulous voice, “I shaved it off myself, for us. Isn’t that the way you young studs like it now?”

“Um, speaking for myself, yes I like it, especially on you. And if you don’t mind me saying so, you have a very attractive pussy.”

My eyes were fixed on her full, puffy labia, the largest I had seen. Not that I had seen that many, to tell the truth.

Mrs. Bloom laughed and said, “That’s the first time my pussy has received a genuine compliment, and I thank you very much.”

Then she turned and headed down the hallway, letting the robe fall behind her and forcing me to step over it as we made our way to her bedroom.

Sitting on the edge of her king-sized bed, she patted the sheet beside her indicating that I should sit next to her. She was staring at me, her eyes locked onto mine and I wondered what would happen after I joined her on the bed.

“I guess your husband isn’t home, huh?” I managed to get out.

“Wouldn’t it be weird if her were?” Mrs. Bloom replied in a husky voice.

“Yeah ... I don’t think he’d like it one bit.”

“Nooo, I suppose not. But you know some husbands like to watch. Did you know that?”

“No, I didn’t. Is that really true?”

“It is they call them cuckolds. They really get off watching their wives with other men, or even women.”

This was news to me, and so I let loose with an appropriate, ‘Wow!’

Meanwhile, her hand was on my arm, her scratching their way down my forearm, leaving a red trail in their wake. Her perfume was intoxicating.

I let my eyes devour her breasts; only marginally inferior to my sister Stephanie’s, that are, in my humble opinion, world class. Suddenly I realized her mouth was against my ear, and she whispered: “I need to remind you, Howard ... you tell no one about what happens here. I want you to swear it.”

“I ... I swear to God, I won’t tell a soul about what happens here, Mrs. Bloom.”

She pulled her head from my ear and I turned to face her, glancing down at her tits first and noticing that she was breathing heavier. I raised my gaze to her face and saw her lips were slightly parted and her eyes were bright---she looked---ready.

“You’re the hottest woman I’ve ever seen,” I lied. She was gorgeous, but not as much as Stephanie, or even Candy. She edged out Regina and leapt past Becky and Sydnie-Ann by comparison.

“Oh, I like that answer, Howard!” she purred in a sultry voice, “I really do.”

“You ... you do?” I said surprised at the effect my comment had on Mrs. Bloom.

Once again I sent out a mental thank you to Candy and my sister for coaching me on proper etiquette in complimenting women.

My cock was fully erect and pants were so tight I knew it was visible and made sure to keep my hands down.

“Why wouldn’t I?” she asked, “Let me tell you something, Howard. Those girls weren’t fighting over you for nothing. You’re one hell of a good looking boy. Those bedroom eyes with that dark brown hair, mmm-hmmm” she nodded, and this...” she touched my erection with a long nailed finger... “is quite a tempting morsel.”

“Why don’t you take some of those clothes off? I’m getting embarrassed sitting next to you in the all together and you fully dressed.”

As I stood up at the side of the bed and disrobed, she ran her hands over my chest, shoulders and calves before cupping my testicles and purring, “I just love a man with big balls. They seem to be better in bed than the average guy. Are you average, Howard?”

“Um, no, I don’t think so.” I managed without stammering.

Arching her eyebrows, Mrs. Bloom said, “Really? You know this, how?”

I had my answer ready and used it quickly. “You said it yourself. Reggie and Becky weren’t fighting over me for nothing.”

She laughed loudly and raucously and slid her hand behind my head and up through my hair.

“Howard,” she said languidly, “I’ve wanted to fuck a student for a long time. Day in, day out, year in, year out, all you beautiful boys parading past me, ogling my tits and ass. I know full well most storm off to the nearest bathroom and jerk-off thinking about what they might do to me, or with me and I’ll tell you it’s made me hotter than a two-dollar pistol.”

Her tongue grazed my ear again, but this time I stayed still and bit back a moan as her wet tongue trailed down my neck.

“But I couldn’t take that chance could I? And it would be wrong to do, but you my dear are certainly an exception to the rule.”

She paused, took a deep breath and said, “Just between us, I’m leaving the teaching profession at the end of this semester. She took hold of my erection and gave it a friendly squeeze.

“Sooo, Howard, this is my last chance to fulfill my little fantasy.”

I started to speak, but let out a surprised moan as Mrs. Bloom started rubbing her hand along the length of my cock.

“Which means you, Howard, get to fuck your hot teacher, and I...” she squeezed a drop of precum from the tip of my cock and laughed delightedly... “Get to be the nasty little cougar I want to be.” Slowly licking her lips she gave me another squeeze, “This is going to be one young cock I’m not going to tease, I promise you.”

“Oh...” I managed and reached out to fondle the closest breast.

“Like them, Sweetie?”

“Oh...” I swallowed as I took in her large round tits with their hard pink nipples. “They’re perfect.”

“Yeah, I kinda think so myself,” she purred as she cupped both breasts and held them up for me, “Are they as nice as you thought?”

“Better.” I said and reaching out tentatively to rub the nipple on her right breast.

“Don’t be shy baby,” she whispered, “Play with them; show me how bad you want them.”

With part of my mind wondering when I was going to wake up I placed both my hands over her tits and began fondling them. They were smooth and firm and I could feel her nipples pressing into my palms. I removed my hands and began rolling her nipples between my trembling fingertips.

“Oh, that feels nice,” Mrs. Bloom purred, “But here let’s make it better.”

Taking my wrist she pulled my hand up to her face where opening her mouth she wrapped her soft lips around my fingers and started swirling her tongue around my fingers.

“Oh damn.” I said softly.

“Thinking about where that tongue will be later?” she asked as she placed my hand back on her nipple and brought the other one to her lips.

“I’ve been thinking about that for a long time.” I answered while watching her pink tongue play across my finger tips.

Lowering my hand she smiled, “So have I.” She paused to moan softly as my now moist fingers stroked her nipples. “I’ve gotten off to you, Howard, even shoved a vibrator deep into my pussy and imagined it being this nice young cock of yours.”

Her lips were parted and she was breathing heavily causing her beautiful tits to heave beneath my touch.

“Is that all your going to do is touch them?” She asked, opening her eyes, “Let’s see that so-called talented tongue of yours?

Opening her eyes, she reached out and grabbing the back of my head pulled me down to her chest. Eager would actually be an understatement to describe the feeling that went through me as I opened my mouth and sucked her supple flesh into my mouth. I took as much of her tit as I could along with her nipple and began swirling my tongue around it.

“That’s it ... suck that tit!” she moaned as her fingers ran through my hair, “The very tits you’ve jerked off to!”

I switched to the other nipple and this time made a show of teasing my tongue around it and was rewarded with a soft moan and her whispering, “Oh, that’s soooo fucking hot!”
I moaned around her swollen nub as her hand started moving on my cock again. I began rocking my hips, my aching dick straining for release. Mrs. Bloom wrapped her fingers in my hair and pulled gently. Getting the hint, I reluctantly sat up.

“Don’t worry, Howard, you’re going to get plenty of my tits, but you’re awfully excited and I think maybe I’ll help you relax before you take good care of me.

I nodded dumbly as my mind started to spin at the thought of what that meant.

“But we need to do some kissing first ... is that okay?”

“Yesssss...” I croaked. I started to say something else, but it was cut off by Mrs. Bloom leaned in and kissed me hard. I opened my mouth and groaned as her tongue entered it while her mouth devoured mine. Her hands slid up my chest and her arms went around my shoulders while her tongue danced across my teeth before her lips started sliding softly back and forth as she slowed the kiss down.

“Oh, Christ, you have such a nice hard young body!” She plucked at my nipples and I realized what it was that women felt when I did it to them. Pure pleasure.

I cupped her ass and pulled her in for another torrid kiss. Apparently it caught her off guard, but she went with it and we kissed for several lovely minutes during which I teased her anus no end.

“Where’d you learn that?” she asked breathlessly when our mouths separated.

“I can’t tell you who, but I’ve been with a couple of older women. By that I mean older than high schoolers.”

“That how you get these high school girls, Howie?”

“Probably, but I really don’t know. I know enough to talk to girls like their people and not sex goddesses like most guys do. That separates me from most. I’m not the quarterback or the best looking, or best dancer, but I dress well, and like I said, I listen to them and do not kiss and tell.”

“You’re well coached, Howie, especially the last part, not kissing and telling. Most guys can’t wait to brag about the slightest thing they get away with on a date.”

“I know. I fend off at least a half dozen questions about my sex life everyday at school. It’s about the only thing guy’s talk to me about. I just smile and keep walking. But I’m starting to weaken. I really need some male friends. Any advice along those lines?”

“Mmmm, yes, perhaps I do. Suck on this nipple for a while, will you?”

I did, and Mrs. Bloom suggested finding someone I could trust, and then coach him on how to approach a girl. Then help him connect with a girl I wasn’t interested in.”

Letting the nipple pop from my mouth, I told her I thought that was great advice and knew just the guy to try it on.”

Mrs. Bloom murmured something I didn’t understand an yanked my underwear down to my knees. My hard cock sprang free and her brown eyes widened as she made purring sound in her throat before saying, “Ohhh, look at that cock! Now I know why the girls fought over you!”

Reaching out she wrapped her red tipped fingers around my shaft and squeezed.
I moaned at the feeling of her soft hand around my shaft and again when she squeezed harder and a stream of sticky precum squirted out.

“Oh, that looks so good.” She whispered as she continued to squeeze.

I released a sound that could only be described as a whimper when she wrapped her hand even tighter around my dripping prick, causing more precum to ooze out. My hips jerked involuntarily when she rubbed her palm across the sensitive head of my dick. I felt my legs start to tremble and my hands tightened on her shoulders as she swirled her hand around several times.

“Let’s get this cock nice and sticky,” she said softly and began stroking me. Her precum slickened hand felt fantastic, and I let myself relax as she slowly pumped me.

I began breathing through my mouth as my heart beat faster in anticipation of her mouth. She licked her lips and bending her head, kissed the purplish tip of my cock.

“Ohhhh, fuckkk,” I gasped hoarsely as she pulled her lips back, taking a line of my precum with it.

Mrs. Bloom slurped the residue of cum into her mouth and made a show of sucking her way along the sticky trail until her lips were pressed against my cock.

“Mmmmm, you like, Howie?” she asked.

“Y ... yes.” I stammered as her tongue flicked out and traced the head of my cock.

“Good. I wouldn’t want to disappoint you; after all I am supposed to be a nasty MILF or cougar aren’t I?”

“You can be anything you want to be.” I groaned as she made a show of trailing her tongue down the front of my shaft.

“And no worries because I love to get down and dirty.”

That sentence was punctuated by her lowering her head and sucking my balls into her mouth. I made another pathetic sound as she released my balls from her mouth and began tonguing them. Her eyes were fixed on mine and I noticed her hips rocking back and forth as she swirled her tongue from one side of my balls to the other. She was still holding my cock and running her finger nails up and down. Her teasing touch was driving me crazy and my own hips started moving, thrusting into her hand.

“Oh, someone wants to cum don’t they?” she asked.

“Yes ... oh please.” I moaned as she wrapped her hand tighter around my cock.

“That’s the problem with you young boys; it doesn’t take much does it?”

“Please don’t tease me!” I was whining at this point.

Mrs. Bloom laughed and despite the fact that she was licking my cock I began to blush again.

“No worries honey, if I were a tease I wouldn’t be licking your cock. Now just relax and enjoy, I’m going to give you the show you’ve been dying for and I’m going to suck this beautiful cock until you cum in my mouth,” she smiled up at me, “Would you like that?”

“Yes ma’am,” I said forfeiting any chance of taking charge of the situation. I guess what I mean is she was my teacher---a position of authority. And yeah, I know my Aunt Elaine was also an authority figure---my mother too, for that matter, and I told them what to do---at times. But I was 100% under Mrs. Bloom’s thumb.

“Play with my tits while I play with this cock of yours.”

I quickly cupped her heavy tits and began playing with her nipples. She closed her eyes and released another one of those sexy sighs. Opening her eyes, she bent her head over my cock then looking directly up at me, made a wide ‘O’ with her mouth and enveloped my cock--well half of it.

The sudden warmth of her mouth was overpowering. She bobbed up and down several times then opened her mouth allowing a trail of saliva to drool out and cover my cock.

I pinched her nipple and moaned simultaneously just as she gobbled me up again. Now she was making sloppy wet sounds as she slurped her spit from my cock. I switched from playing with her nipples to just fondling her tits in fear I would get too excited and pinch her to hard.

I sighed softly and again forced myself to relax and enjoy the incredible sight of my cock sliding in between those soft red lips. She kept taking me deeper and suddenly her mouth was pressed against the base of my shaft. She held me there and began shaking her head back and forth.

“Oh damn, that ... oh! Ohhh! Ohhhhh!””

Her tongue was sliding around my cock and I couldn’t believe how good it felt. My cock was buried in her warm, wet, mouth and her nipples felt as hard against my palms as my cock felt in her mouth. Almost as good was the sight of her ass grinding in small circles and she was beginning to moan around my cock. Blowing me was turning her on. Double Damn she was fucking hot!

I took in the red smudges of lipstick as her lips and tongue pressed hard against my shaft. She released my cock with a loud sucking sound and moaned, “Oh, that young cock of yours tastes so fucking good!” Then she winked and added, “I can’t wait to taste my pussy on it!”

Again my only answer was a sound of pleasure when she started pumping my cock in her fist, and suddenly stopped. “Fuck, I forgot! Let’s try this, Howie!”

Without waiting for my reply, she got up on her knees, gently removed my hands from her breasts and covered them with hers, then lifted her tits and wrapped them tightly around my cock. I moaned when she began bouncing up and down, causing my cock to slide between her soft breasts.

“You like that, Howie?” she asked, “You like tit fucking your teacher?”

I thought of doing the same thing to Reggie and my Aunt, and then forgot all about them as Mrs. Bloom lowered her head and took the tip of my penis back into her mouth only to let it fall away as gravity took hold.

“YES!” I gasped, only to lose my voice when her chest rebounded and, her tongue was there to lick it.

I was soaring ... ready to ejaculate any second.

“Fuck those tits, Howie! Go on; fuck ‘em!”

I was breathing hard and sweating, lifting my hips and sending the head of my cock into her waiting mouth; and each time the tip of my cock slipped between her mouth I released a small gasp of pleasure. The feeling of her firm tits around my shaft and her wet tongue, never mind the visual of fucking her tits, had my legs shaking uncontrollably.

She pulled back, causing my dick to slide away from her cleavage. Then with a lewd laugh, she took me back in her mouth and sucked furiously. I reached out and wrapping my hands in her thick hair, started pulling and pushing her head, guiding it as she blew me.

Mrs. Bloom moaned along with me and started sucking even harder.

“Gonna cum!” I croaked in warning as her hot mouth plunged down yet again and I felt my load racing toward the end of the tunnel.