Chapter 27: Tonya is Deflowered

This chapter has facials and 1^st time
Dorothy still had the look of debasement but physically was plenty ready for fucking. And Lisa seemed to be thrilled with the newfound joys of having a dick in her cunt. She welcomed another of the team to partake in it after the new teammate squirted his load in her. I let the last of the team in, and they, like the rest of the team, stood frozen for a minute at the scene. But they, too, quickly made their way to Dorothy and Lisa. Tonya was upset by basically being ignored by the boys who came in despite her being naked on the bed with Lisa.

Finally dismayed her body wasn’t considered attractive or desirable enough to screw, she came over to me. She climbed into my lap like Cheryl had done many times. She said, “It’s not fair. Just because of my hypogonadism menstruation, and amenorrhea, I don’t get any tits, and my pussy doesn’t have any hair doesn’t mean I’m not a woman. I may look like a twelve-year-old, but I have a period just like Lisa over there. In fact, she and I have it at the same time. Our last one showed up on her birthday, ruining it. I’m never going to have a guy into me because guys want tits. God, I hate my body.”

I actually considered screwing the teen as I sat there and thought, ‘Well, maybe screwing this girl would be doing her a favor. It would let her know that despite looking like a twelve-year-old, somebody still finds her desirable. Somebody that wasn’t a pedophile or that did nothing but little girls that looked like her.’

Trying to make her feel better, I said, “Yeah, sometimes life’s not fair. But I’m sure somebody out there will find you attractive. I mean, I do.” That was all she needed to hear from me. She started to undo my pants to free my dick that had been so far that weekend overused. I tried stopping her. I moved her hands from my pants, but she kept returning them determinedly. “As I said, I find you attractive. I just don’t think it’d be right for me to have sex with you right now.” She covered my mouth with hers. Not accepting my objections and preventing any more, she continued pulling my recuperating cock from my pants.

She said the words that many a guy has said to a girl. “Lift up your hips. I need to take these off.” The desperation in her eyes and determination in her voice convinced me to let her have her way. She needed to be like the other three females in the room, desired. She fiercely wanted someone to give her the sensations that came with enjoying her body. The added plus for me, besides getting to savor being the first one to put a cock up her, was Dorothy would see a girl that looked like Helen and Jane riding my pole. Maybe giving her a preview of what it would be like if I were to screw either of them.

I lifted off the seat cushion and let her slide my pants and underwear down my legs over my thighs. She further pushed them down my legs and off my feet. Figuring in for a penny in for a pound, I raised my arms. She understood the implication and finished stripping me, removing my shirt. Naked, she climbed on me and straddled my hips. She pressed her naked body to mine. The hard bumps on her chest pressed into me while she and I Frenched for a few minutes. She rubbed her hairless slit up and down along my dick. Her lube and cum, as well as Lisa’s spit from earlier, coated my hard rod from tip to base.

Her whole body trembled as she climbed higher on me, putting her underdeveloped breast to my lips. I took all of the smallest breasts to ever have touched my lips between them. The buds felt like nothing I had sucked on before. They were hard but no bigger than a golf ball and had a solid point on the mushy cone they sat atop. I swirled my tongue around the cone, scraping my teeth over them. There was a low, growled groan that didn’t belong in such a petite, lissome teen after each time the soft flesh scraped under my teeth. I nipped at the hard bud on the top, only to have her hands go to the back of my head and jam my lips back flat on her ribs.

With both her nipple-only type breasts slick with my spittle, she slunk down. Tonya put her lips to my ear and whispered. “I’ve not done this before, and I’m scared. But I want to do it ... I need to do it. So can you go slow? I don’t want it to hurt.”

I didn’t have any idea why she thought putting a cock the size of mine into a body the size of hers for the first time could be done without it hurting. At least for a while. Still, I assured her, “I’ll do what I can.”

All of her quaked even more as she raised up again on her knees. One last painting of warm lube and cum on my dick prepared it to part her nubile lips. I felt the fleshy folds first, then the fine, satiny ones on either side of my piss slit, but not much further down my head. She aligned my dick to her tiniest of holes. Not only did her condition prevent her hips from widening and her breasts from fully budding out, but her vagina was also not fully developed. Though from what she said, she was fully capable of having sex with all the implications sex brought.

The tip of my cock scarcely fit into the indentation of her pussyhole. It made me wonder how the girl would ever take all of my rod deep in her. She quivered and lowered herself hardly at all, immediately whining into my mouth as my dickhead widened her underdeveloped, unused passage. She huffed and groaned even more when my dickhead ran into the thin wall within her that was her maidenhead. She gradually pushed down on me, only to hop back up when the pain of my dick stretching her hymen became too great. I surmised the only way she would ever fully get on my dick was if there was one hard thrust. It would shatter the barrier to her womb’s foyer and the rest of her lusciously hot tube.

Kissing her, my hands went to her shoulders and up the back of her neck. I held her tightly to me and thrust my tongue deep into her mouth. I did the same, thrusting my dick up hard into the tight passageway while pulling down on her shoulders. More than half of my dick passed into her, obliterating the virgin barrier of her pussy.

Dorothy had been watching us out of the corner of her eye. The whole time, she sucked on one dick while another teammate was sliding his five-inch rubber-covered dick in and out of her sodden pussy. The five-inch dick thrusting in and out of her had kept her on the edge but wasn’t enough to push her over the edge to climax. When Tonya wailed incoherently into my mouth, Dorothy turned her head, no longer just looking at us through her peripheral vision. She stared as Tonya was skewered on my hard rod. Her entire body tightened as half my dick was rammed up the tiny passage, taking her virginity. There were another four inches still yet to enter the teen’s petite, underdeveloped body. At the time, Tonya’s muscles were involuntarily constricted, her hymen torn to shreds, and she wailed into my mouth.

Despite the wailing, she redoubled her determination to fuck me. She lowered even more of her vagina onto me. My cock had invaded only a small part of her overly tight tube. Her body resisted my ingress only to accommodate my squashed tool. I felt the tears that had run down her cheeks on my lips, and her breathing was labored in my mouth as we Frenched.

She continued her tearful moans and groaning as, with grit and determination, she had my cock head an inch further within her. The stretched orifice crushed my dick like nothing I had ever experienced before. Even when I’d had other small-stature women clamp down on my dick while climaxing, this was a squeeze like no other. I could feel her walls rippling at the new dimensions; I was demanding of them. The tears flowed freely down her cheeks as she remained mostly off my dick. But she slowly took more of my crushed head into her whining and grunting the whole time. She bit her lip or mine as the pain of being filled passed from her pussy to her brain.

The wailing drew all of Dorothy’s attention. She turned her head, no longer just looking at us through her peripheral vision but staring as Tonya was skewered partially down my hard rod. Having Dorothy looking plainly at us, I suggested, “Here, let me try something new. It’ll probably make it feel better faster.”

The crying girl took her mouth off my shoulder, where she had been biting me to endure the pain by inflicting some of her own. She nodded yes and sobbed, “OK.”

I stated, “I think you’ll like a little reverse cowgirl.”

Tears were still streaming down her face, crying. She continued huffing, her muscles trembling. “What’s that?”

“Let me show you,” I answered. “But I need you to do what I say.”

Her thighs quaked from squatting over me so long, unsure of going down further and not willing to admit defeat by getting off. As not taking my dick fully would be the same as saying her appearance was what she truly is, a little girl. She again nodded, unable to speak through her sobs and huffing.

I put my hands under her rounded ass, supporting her. I then started coaxing her leg up. “Move your knees up to your underarms and ball up a little.” I had tossed Cheryl and Helen from this position. So rotating Tonya and keeping her balanced on my shaft wasn’t beyond the realm of possibility. She mindlessly did as I said and held her legs up, wrapping her arms around them. Still, she moaned and cried out as gravity pulled her ninety-pound body down another half inch.

She moaned and looked down at the junction where my dick entered her as I rotated her on my cock. Her pussy walls twisted on my dick in a way I had never felt before. A way that would be having me buy a sex swing. I stopped turning her when she faced out to the room. Enabling her to witness all the transpiring sex and see the joy on all the participants’ faces. It was one of my immediate goals. Tonya would see how happy the other people fucking were and realize she would be too at some point.

I could see in the mirror across from us that her face still looked pained, but now also looked panicked at her situation. Tonya looked up into the room, scanning for the sounds of moaning coming from Lisa, Penelope, and Dorothy. A full frontal view of the teen’s underdeveloped body, from her golf ball breast buds to the oval of a few sprigs of brown pubic hair over her baby smooth labia, Tonya’s was on display for anyone in the room. Only Dorothy seemed mesmerized by it.

Tonya, who likely looked like a two-year earlier version of her daughter Helen, skewered halfway down my pole, affected Dorothy. But not in the way I thought possible, seeing my dick in a girl that looked like her daughter. Plus, the doppelganger had wailed out as she lost her virginity and still had four inches of dick to enter the deflowered cunt. So, I didn’t expect it to excite Dorothy. But the edges of her mouth turned up in a smile as she sucked harder on the cock in her mouth.

Tonya continued moaning and gasping, with a small bit of pink lube escaping from the stretched pleasure hole. Its appearance running down my dick was the catalyst for Dorothy finally passing over the edge to climax. She trembled and arched slightly, groaning out past the teen dick that was in her mouth, and orgasmed on the small dick in her pussy.

The boy behind Dorothy, fucking her, was proud of himself and said, “Damn, I made the slut cum.” He continued banging his dick into her. The smack of his pelvis into Dorothy’s ass continued to sound in the room over Tonya’s moans and Lisa’s thrust grunts. While I continue easing Tonya down my rod under the watchful eye of the orgasming Dorothy.

After having frozen for a few seconds, climaxing, she started to rock on all fours. She slammed her cunt hard back into the small dick in her. Dorothy’s pussy was looking for more than the small dick could deliver. She grunted with her mouth open, no longer sucking on the cock in front of her.

She had already done a good enough blowjob for the ballplayer. Having the woman suck his dick for over a minute was enough to draw the balls of the boy uptight to his body. He started to shake and have his ass tightened with his own orgasm. Dorothy, though, with her lips no longer around the boy’s cock, opened her mouth wide and let out a low, growled moan, “Augh!” The twitching cock ended up outside her mouth as she banged against the dick doing her doggy style. She hammered away against the pelvis of the boy behind her, pushing the butt plug into her. It made her groan all the louder.

The youngster didn’t keep his dick aligned with her open mouth as it started spewing. The first rope splashed diagonally across her face. The long rope of cum clung to her face as the next burst forth and coated more of her skin. The opaque goo hung onto her nose and forehead. While some ended up in her hair. The kid evidently found it fun spraying Dorothy with his spunk. He didn’t try putting his dick back into her mouth. Instead, the rest of his jets landed in Dorothy’s hair and along her neck and face.

The youngster then said to his friend, “Look man, I plastered her face with my spooge. She looks so slutty with it dripping off her nose.”

The boy next to him, Javier, had his dick in his hand. He was ready to replace his teammate and get his first blowjob. But complained, “Damn it, Dan. I don’t want to get your spunk all over me while I have this whore sucking me.”

Dan nonchalantly said, “Sorry, dude, but it was fun hosing her down.”

Pea heard the boys’ exchange. She pulled her lips from Tom’s but left her hand on his cock, stroking it lightly. To Dorothy, she said, “Slut, clean yourself up. Wipe that spunk off your face. And clean your hands when you’re finished.”

Dorothy didn’t dare ignore Pea’s command. For a few seconds earlier, she had looked ashamed at the orgasm that had passed over her. The look of shame added humiliation as she wiped the goo from her face, spreading it out as she did so. And like a cat cleaning itself, she licked her paw clean of the cum that ended up on her hand. The new boy must’ve considered the cleaning Dorothy did of her face enough that he could get his blowjob. In that light, he grabbed her hair, yanking her face onto his hard dick.

Dorothy still watched me and Tonya as she sucked on the dick that gagged her at first. She backed off only a half-inch or so, and her gagging stopped. The sound of gagging had no more stopped than Tonya’s legs holding her aloft gave out for a second. Having my cock stretch an inch more of her small velvet-lined pussy. She instantly sobbed as she moved back up the inch. “Oh shit! Your dick is splitting me. You’ve torn my pussy apart.”

Hearing the first coherent words about my cock eradicating her virginity and stretching her cunt coming from a girl that looked a lot like her daughter got Dorothy wound up. Seeing the tears and hearing Helen’s doppelganger whine overrode Dorothy’s shame and humiliation. It had her suck harder and bob her head faster on the dick in her mouth. She was a woman on a mission to have the dick spew. So, she could suck down the cum and get to the girl and ease her pain. Then maybe Tonya would relax and have a fleeting glimpse of heaven sex could bring.

The dick owner’s premier blowjob didn’t last that long when Dorothy increased her suction, bobbing, and licking around the shaft in her mouth. I saw the boy’s ass clench, and he drove Dorothy’s head tighter into him. He smashed her nose into his recently filled-in pubic hair. His dick jumped in her mouth, which eagerly swallowed every blasted wad of cum. She sucked the dregs out of the piss slit, to where, after the pop of the dick coming out of her mouth occurred, no semen was left to dribble out.

The older teammate with his cock in Dorothy’s cunt grunted and held onto her hips shortly after she was no longer being face-fucked. He too drove his cock further into Dorothy’s body, pressing the buttplug deeper as well. He let out an, “Ah ... fuck yeah,” with the first jerk of his cock.

Dorothy, too, despite her self-disdain, arched slightly. She shoved back hard against the dick, spitting cum into its rubber sheath. Dorothy got the warm sensation of the cum without having the goo clinging to her cervix and walls. She, too, gasped, “Oh yes.” Her ass and thighs also clenched after shaking for a short time. She panted and purred loudly as her face fell to the carpet, raising her ass higher.

She was grinning ear to ear with a look of contentment as the used rubber full of dick and cum backed out of her dripping pussy lips. The contentment changed the instant she looked up to see what had caused her daughter’s resemblance’s bawling. “Fuck, too much ... It hurts ... It’s too big ... too full ... can’t breathe. Go back.” Dorothy saw I had moved Tonya down another inch on my dick. Plus, I was looking at her face after her outburst. Seeing me looking at her had turned the contentment into self-reproach.

The additional inch of cock in Tonya’s cunt had required my dick to overcome her tube’s fierce resistance to the stretching by my cockhead. The plush walls did, though, give way, allowing my dick further into the teen, but their payment was sensations of pain and pressure going to her brain.

I reached around her small torso to use Tonya’s tits to guide her further down my rod. On any other woman, I would have handfuls of tits to hold on to. I ended up with only nipples to roll with my fingers as I held her chest. She again whined and groaned when my cockhead continued up her and pressed on the entrance of her womb. The funnel-shaped opening was pushed down by the underside of my cock. It rubbed along the protruding opening, going deeper into her. My slightly larger-than-average meat required another two inches from the smaller-than-average pussy after contacting the back of her vagina. Pinching her puffed-out nipples between my fingers and clasping her rib cage with the rest of my hands, I forced Tonya down the last couple of inches. So, I wasn’t just stretching her pussy’s diameter any longer. But my cockhead distended her small cavern deeper into her pelvis. The extra length let the completely hairless pussy lips rest against my root.

She exhaled heavily without drawing a new breath. Her eyes closed, and she threw her head back into my chest, jutting what there was of hers out. She snarled, raspy and breathless, “Fuck, your dick is in my throat. It’s gone all the way through me. Get it out! It fucking burns ... I can’t take it ... Take it out.” She continued heaving and rigidly squirming as she endured the new painful sensation of being completely filled. I ensured she stayed there huffing and whimpering, her body stiff as a board. The initial louder outcry done, she whined repeatedly, “So deep ... so fucking much ... In my pussy ... God so wide ... so full.”
My dick was way further in her than even I thought possible. I couldn’t imagine the throb my dick caused in her pussy and ultimately her head. I could feel her walls rippling and twitching hard against me, unaccustomed to being opened so wide and so deep. I tried to alleviate some of the discomfort and lessen the pain by massaging the nipples on her exposed, small, golf ball-sized buds.