Story Info: A student is taught by the school’s SSBBW counselor.
I’m so nervous I can barely think straight. All the rest of my friends have already gone farther than this, at 18 I’m pretty sure I’m the only virgin left in my school.
“Focus on your school work!” That was the order from every adult in my life. I knuckled down starting in the second grade, a full ride to a prestigious college didn’t allow for many distractions. It meant that I was on course to be valedictorian, I didn’t have much in the way of a social life. A few friends from study groups, people I’d talk to at my extracurricular activities, but I didn’t think there was anything beyond that for me.
That is until I took my sex ed class. I go to Good Missionary High School, I was there the day Ms. Higgs taught Jerry a lesson. This is a little embarrassing, but she was the first woman I’d ever seen naked. My parents pay a lot for the ultimate purity filters on all of the devices at home. But there, that day, I learned my real obsession, I love breasts. The way Ms. Higgs’ breasts swayed in the air as she danced for the class, the way they bounced up and down as she rode Jerry, the way they flew around as she was then pounded by Carl from the football team. I was like everyone else that day, a hand down my pants till I messed up my slacks. Unlike everyone else, I didn’t have anyone to go with later. I still use those memories to get off, the bounce in those boobs was hypnotic. But I wish they had been bigger.
I became obsessed with breasts, the bigger the better, but hopeless with women. Still, some of the guys decided to help me out. That’s how I got here, behind the bleachers in the gym with Vicky Rathaport. She wanted a new car and she knew how to get it, she was 18 and gorgeous. Tall, mousy brown hair, an hour glass figure and some big breasts. She’d make out with you for fifty bucks, a hundred and you could feel her up, two hundred got her topless, five hundred and she’d have sex. Rumor was that for a thousand she’d let you cum inside. I only had two hundred.
“So you just wanted to look?” Her voice is a mixture of sarcastic and bored as she leans back against one of the metal supports, her shirt completely unbuttoned and her bra on the ground.
I want to say something sexy, to be the suave Han Solo rogue type and make her yearn for me. Instead my voice cracks as I ask, “What size are they?”
“Oh shit, you’re one of those? Here I thought getting to be with Jason McWhirter, there might be a little stimulating conversation. Instead you just gooning over cup sizes? I’m a d cup. You actually going to do anything or am I going to stand here and catch a cold while you jack off to my bra size?”
It was hard to move, just the sight of those amazing breasts had me so hard. Creamy pale, perfectly rounded bell shaped breasts that looked to be more than would fit in each hand. The areola on each was perfectly round and just maybe two shades darker than the rest of her skin, topped by just the smallest pink blush nipples. I moved forward slowly, finally close enough that I could smell her rose perfume. My hands started to lift slowly.
“We don’t have all day!” She said angrily and grabbed my wrists and shoved my hands to her chest. The warmth from those mammaries in my hands was a direct contrast to her icy demeanor. “See! Just titties. Feel them, squeeze them, pinch my nipples, jerk off and get out.”
I pressed my fingers in, surprised by how supple they were despite being firm and perky. Her skin moving between my fingers as I squeezed, then quickly resuming their shape as I let go. My thumbs rubbed her nipples lightly as I kept groping her chest and I was rewarded by a slight moan as they hardened. I looked into her eyes as I just caressed her breasts and stroked her small nipples. The tough girl was leaving, being replaced by a woman who was actually enjoying what I was doing. I leaned in and gave her a gentle kiss on the mouth, my first kiss. Before I could pull away I felt her hand on the back of my head hold me in place and her tongue pierce my lips to claim my mouth. I gripped her harder, kneading each breast in my hand but making sure to keep rubbing her erect nipples.
She leaned her head back, breaking our kiss “Suck my nipples.” She said breathlessly. I looked down at her chest still cupped in my hands, the creamy flesh now mottled pale and crimson from where my fingers had left marks in my eagerness. She must have enjoyed whatever I had been doing as she had her right hand down the waistband of her skirt. I lifted her right breast up as far as it would go causing her to give a small cry as I stretched her, moved my head down towards that enticing nipple, wanting to taste and suck the first breast of my adult life.
“WHAT ARE YOU DOING?!”
Vicky and I both jumped as Mrs. Octavia Pratt shrieked. She was the oldest teacher here, a withered crone who had scared death into letting her live forever. Vicky tried to cover up but no one could button a shirt that fast, besides how would we explain her bra on the floor anyway? Mrs. Pratt waited till Vicky was decent, well decent enough as you could see her nipples poking into her shirt as she was now braless, and we were marched to the principle’s office.
Principle Benson was a fine vision of femininity herself. A tall and lithe woman with her blonde hair always in a bun on her head. She was rather flat chested so had never really featured in my fantasies but I knew some of the guys worshipped her legs. She wore a severe expression as Mrs. Pratt explained the situation.
“I can’t even believe this! Our school’s best and brightest and the cheap whore, both in my office. What were you thinking?”
I was stuck looking for an answer when Vicky said, “I was thinking I was enjoying having my breasts massaged and was going to have my nipples sucked. Damn things are still erect and aching for attention, to say nothing of what is going on down in my…”
“That’s quite enough Ms. Rathaport.” Principle Benson said, though there seemed to be a lump in her throat and the way she looked at Vicky had changed in a way I can’t really describe.
Pulling her attention away from Vicky, Benson fixed me in a glare, “As this is your first offense here Mr. McWhirter, I will dispense with punishment for now. However you must report to the school counselor at the end of the day. I won’t be having our best and brightest stumbling at the finish line. You’re dismissed.”
I stood up quickly and walked out of the office. The door closed behind me and I was so nervous and relieved that I just had to lean back against the door and catch my breath.
“What am I to do with a bad girl like you?” I heard the principle ask.
“Whatever you’d like mistress.” was Vicky’s shocking reply.
I wanted to stay so badly and listen but I was in enough trouble already so I did my best to wish the tent in my pants to go away and walked off to my next class.
The rest of the day was a blur. I had been farther with a woman than ever before, been able to feel warm breasts in my hands, I couldn’t concentrate on anything else. Just drifting from one class to another, my erection coming and going like the tide. When the final bell rang I was so distracted I almost missed it, I planned to go to the restroom and take matters in my own hands, but then I heard the school secretary come over the PA and call me to the counselor. That reminded me of Ms. Benson and Vicky, and my erection was back in force as I imagined all the ways our strict principle might be disciplining Vicky.
So I ended up in the rather spacious office of our guidance counselor, I hadn’t met her before as she had just replaced our previous one last month. The name plate on her broad and solid oak desk read Ms. Renee O’Rourke. The rest of the desk was remarkably free of clutter except for a lone laptop. The room had no windows, lit only by the fluorescent lights in the ceiling. A single potted plant on top of the filing cabinet in the left hand corner of the room provided the only natural color. I took the only other seat besides the one behind the desk. The chair was large, closer to the size of a loveseat. I tried to focus on what may lay before me, but I just kept thinking about the way Vicky’s nipples hardened under my thumbs.
“Thanks Ms. Higgs, I’ll do my best.” I hear a voice from behind the door, it’s light and airy with the slightest lilt of an Irish accent. I turn to see who it belongs to as the door opens and Ms. O’Rourke walks into the room. She actually sidesteps through the doorway and I can’t believe what I’m seeing. She must be at least six foot and she’s only wearing flats, but there is just so much of her! The large skirt is barely holding on as her thighs and ass ripple with each step. Her stomach actually peeks out a bit from the red blouse that is straining to hold all of her in. But those breasts! Each one seems to be as big around as Vicky’s whole torso and almost as long. Even with whatever specialty bra she must be wearing they hang off of the shelf of her belly. I almost shoot my load then and there. Who knew tits came in this size? I’d heard other guys talk about women they called ssbbws, but to actually be in the room with one?
“Jason? Are you listening to me?” That lilting voice finally cut through all my fantasies. I finally saw her face. Yeah she had a bit of a double chin, but her pale skin with its light dusting of freckles framed by what I assumed to be her naturally red hair caused my breath to catch in my throat. There was a natural beauty to this woman, like the earth mother of myth, a symbol of rich fertility. I think those ancient people were on to something with their carvings of big women.
“I’m sorry, could you repeat the question?”
“What made you think that being with that girl was a good idea?”
I looked down at the carpet, not just out of embarrassment but because it was hard to think straight looking at her. “I didn’t think it was a good idea, it was just…well…my only option.”
“How could paying to touch a woman’s breasts have been your only option? You are an incredibly smart young man, surely there was something else…”
“Yeah cause people actually care about that! You know how much you have to sacrifice in order to be smart? I have no friends, I can talk with people enough to get through a project but otherwise there is no time for anything else! I can barely talk to other guys, much less women.” I blurted out.
“Oh, well, so that means this was…I mean to say…uhm.”
“Yeah, I’m a virgin. Probably the only one in this school.”
She tapped her fingers on the top of her desk as my confession hung in the air. Yeah, it was pathetic. Here I am, the world’s biggest loser, having to tell this pretty woman that I had to pay to touch a pair of breasts because I’m too much of a freak to get a girl on my own.
“Jason, could you look at me?”
My eyes traveled up from the floor, up her desk, but stopped when I saw her still fully covered breasts resting on the desktop. Sitting down had forced her stomach up and despite the fact that the red blouse didn’t show any cleavage, the heavy breasts were perfectly outlined for me. How could anyone walk with those things? Why would you even leave the house? Give me that pair of breasts and I’d be in bed all day everyday. My erection came surging back as I ogled Ms. O’Rourke’s tits.
“I believe I’m beginning to understand your problem. My eyes are up here.” She said in a gentle tone. I looked up sheepishly into those deep green eyes, almost as mesmerizing as her breasts. Her gaze broke with mine as she looked down and an embarrassed smile crossed her face. I followed her eyes and noticed a dark spot had formed on the front of my khakis.
I covered up as fast as I could, I could feel my cheeks burning as she chuckled softly. “I am so sorry! I don’t know how…”
“It’s okay Jason. The body is a natural thing, no need to be ashamed. I’ve just never made any body cum from the sight of me.”
“You know, cum, ejaculate. Usually I have to work a bit harder for that.” She said with a laugh.
“But I didn’t! This is just precum I swear!”
“Prove it.” She said, her voice going to a lower register that made my balls tingle.
I hesitated for just a moment, then stood up and quickly undid my belt and opened up my pants. I pushed them and my boxers down, allowing my cock to spring free. It was so wet it glistened in the florescent light but it bobbed proudly before me. I looked at Ms. O’Rourke and her eyes were captivated by the sight of me.
“All that and never had sex? Now that’s a shame. You must jerk off something crazy.” She said and then her pink tongue ran around her ruby red lips. “You must have been hard all day long.” I just nodded my head yes.
“Well I’m not a nurse but that can’t be healthy. So why not just sit back in that chair and stroke it out for me? We’ll get you all taken care of and then you can think clearly again. That’s it, sit back, make yourself comfortable. Now grip it and stroke up and down, not too fast! Just slow, languid movements. There’s no need to rush.”
I threw off my shirt so I was completely naked then did my best to follow her instructions, but being told how to touch myself by this vision of a woman made it hard to comply. It felt so good having her watch me slide my hand up my shaft, forcing more of the clear liquid out of my dick to wet my hand, then back down to my balls. She moved her hand up and down in time with mine, demonstrating the pace she wanted. Her face became flushed as she watched me hang on her every word. I doubted she had ever done this before, either that or she just liked watching an eighteen year old man masturbate.
“That’s it, keep pumping that hard cock. Now take your free hand and play with your scrotum. Those balls look so big and full of cum. Just massage them. Don’t be shy.”
“I’m not shy…you’re the one behind the desk with all your clothes on.” I said with a bravado I didn’t feel.
“Quite so.” She said and opened a drawer on her side of the desk and put away her laptop and nameplate. Then she stood up and quickly removed her red blouse. I was in awe as those giant breasts were finally exposed to me. Because I hadn’t seen her nipples poking into her shirt I had assumed she was wearing a bra, but as she lifted her blouse up her chest moved with it and as her tits dropped gloriously from their fabric prison to bounce against her stomach and swing freely I realized I was wrong. The freckles of her face extended down her neck and even darkened at the top of her cleavage. Flecks of golden orange trailed down the milk white skin before disappearing just before the barely there blush of her areolas and the small flat nipples. Her right breast was also about an inch longer and looked fuller than her left one, though at their massive size who would complain.
She walked around her desk to lean back against it, her eyes locked with mine, her right hand still indicating my pace. “Is that better? You want to stare at these fat breasts and just jerk it? That girl you were with looks practically flat chested compared to these.” She reached out her arms and embraced her giant breasts, creating enough cleavage to tittyfuck a baseball bat.
“How…” I barely stammered out as she started to shake them, making them move back and forth like the tide.
“How big? Does that get you harder, my breast obsessed little man? Well they’re not exactly the same size, but I’m about a 40 M and still growing. Doctors call it macromastia, I call it a titty lover’s dream. They are just so huge and full. I bet you want to come all over them. To just really let loose and jerk as hard as you can. Do you think you have enough to coat these giant tits? Go ahead and stand up, move over here and see how much you really got. I love licking a man’s salty cum off my breasts.”
My hand was a blur as I managed to stand up. Her dirty talk and those massive boobs, I knew I wouldn’t last much longer. As I got closer to her she leaned over, letting those two slabs of breast meat hang off into the air. I can’t even see the rest of her, just those giant breasts.
“That’s it, faster baby! I want that cum! I need that big load all over these giant boobs, can you give me what I need Jason? Can you please give me that cum?”
I felt that load come up from my toes. I was grunting like an animal and she began this excited laugh as the first strand of cum shot from me and splattered against her left breast. I’ve never cum that much before. Six or seven hard shots before more started to just ooze out of the head. She reached out and grabbed my cock, pulled me closer and rubbed the head of my dick into the soft warmth of her breasts, making sure she didn’t miss a drop.
“Such a good boy. Now go sit back down. I don’t need you getting lightheaded right now.” She said as she stood back up to her full height. I did as I was told and then watched in wonder as she lifted her right breast up and began licking my cum off the tit. My cock hadn’t fully gone down when watching her eat my cum had me hardening again.
She noticed this and smiled, “Principle Benson says I’m to do whatever is necessary to make sure her star student doesn’t falter. Well in my opinion if you are distracted by that boner in class you could get behind, so this is going to be our thing. I want you here an hour before your class starts and for at least an hour after school. I’m going to make sure you have a clear head for your classes.”
She spoke in between licks of jizz off of her breasts. I had already started stroking again. She just smiled at me as she finished cleaning herself off. Then she put her hands to her waist and undid her skirt. She slid it off of her and she stood before me in all of her natural glory. I tried to see if the hair on her pussy was red as well but her stomach rode low enough that it was hidden from view. There was just so much of that luscious belly on display, creamy skin with faint purple stretch marks. She leaned back onto the desk, making it creak, and began to just rub her stomach and breasts, reveling in all of her flesh as much as I was the sight of her.
“Come here.” She said. I was up and over to her in an instant. “Do you like everything you see? You like watching a big girl play with her breasts and stomach? Am I making your virgin cock hard again?”
“Yes Ms. O’Rourke.” I said mesmerized by the way her body moved as her hands kneaded her breasts or shook her belly.
“I think a man who just came on my tits can call me by my first name.” She laughed. “Tell me what you want.”
“Ms. O’Rour…um…Renee, I want…I want…fuck! Oh I’m sorry I shouldn’t…” She reached her hand out a put a finger to my lips and shushed me. When I finally stopped trying to speak, she curled her finger under my chin and guided me closer and then pulled me into her warm body. Her lips found mine and the second kiss of my life was even better than the first. Not that I really knew what I was doing, but she did. I felt her hands come up my arms and bring them up so that I would embrace her just as she hugged me. Her tongue pierced between my lips and she lightly ran her fingernails up and down my back.
My dick was now back to its full strength and I loved the way it felt finally pressed against her warm body. I pressed against her as hard as I could, her breasts moved so that I was between them and I could feel one on each hip, like she was getting ready to tittyfuck my whole body. That’s when I felt it, the tip of my cock finding the place where her skin led up to empty space, waiting for me to thrust in. I was finally going to be inside of a pussy! I began kissing her back hard, stuck my tongue in her mouth and thrusted my hips forward.
It was tighter than I had ever imagined! The ring of her slowly expanded around my cock head. She moaned as I began rocking in and out, but the pressure wasn’t relaxing on my mushroom head. How deep did I have to be in her for that? Her vaginal walls took a second to catch up but finally my cock was gripped tight in her prison of flesh. Then it flashed into my head, I must be passed her cervix. I had heard a jock talk about this, how if you were long enough you could fuck a woman so deep and good she would gladly let you cum inside even though she was guaranteed to have your baby. Her hands left my back and she broke our kiss with a gasp.