Gender: Male Age: 34 Location: Colorado
This is a continuation of a transsexual and incest story. If your sensibilities are offended by that, continue reading at your discrection, having been warned.
For those who have been waiting eagerly for this chapter, no further introduction is needed. But for all others, allow me to recap the highlights here:
Michael had been living with his high school sweetheart, April, but also with a deep secret. When she discovered his cross-dressing tendencies, she threw him out, and flamed what he was doing to all of Facebook.
With nowhere else to go, he went to his sister's place. Jessica not only welcomed him, she had even encouraged him to dress up, if he wanted to. Feeling confident by her offer, Michael transformed into Michelle for the night. That was when he discovered that Jessica knew about his desire to not only cross-dress, but to actually be a woman, and had been planning for this day for nearly six years, ever since she caught Michelle masturbating while wearing her clothes. That night, things quickly escalated, as the two siblings, now forever sisters, made love.
During a confidence-building trip to the mall, Michelle discovered that Jessica had a secret bank account just for her, and she would have enough money to buy whatever she needed to make her transition complete, everything from clothes, hormones pills, and even implants. Money wouldn't be an obstacle for Michelle's transformation.
It was two weeks later, as Michelle was passing for a girl on a daily basis that April popped back into Michelle's life. She was sorry for the way she treated 'him', and wanted to apologize to 'him' in person. She never got the chance, as Michael was no more, and Michelle arrived to accept the apology, while offering her own apology for hiding it for so long.
That night, Michelle came home to an emotional Jessica, who had just discovered that she was pregnant.
To complicate matters further, April decided she wanted to be an intimate part of Michelle’s new life, and asked Jessica to help her do that. As the conversation between them evolved, April figured out two important things: That she would have to be dominating and forceful to get back with Michelle, by not taking ‘no’ for an answer. And that the baby Jessica was going to have belonged to Michelle.
Armed with that information, April all but lured Michelle to their old apartment, and the two made love. Afterwards, as Michelle discovered how much April actually knew about her and her sister. April then invited her to a sleepover, one that Jessica and April had arranged specially for Michelle.
Enjoy the latest chapter.
Sister's Surprise, Chapter 6: The Slumber Party
April and I shared a quick shower after our impromptu lovemaking. She spent nearly the whole time commenting on the changes I was undergoing, from my slowly developing breasts, to the fine hair growing on my mound. "Even with the evidence staring me in the face", she said as she bent over to give my clitty a quick kiss, "I can only see the beautiful girl you're becoming", she said sweetly, before giving me a kiss on the lips.
I left her apartment, my hand holding hers, reluctant to let go, as our grasp slowly slid from each others with our arms outstretched. From the door, she blew me a kiss, "See you tonight, Shelly", she seductively whispered before closing the door.
I drove home quickly, unsure if I hadn't broken a thousand traffic laws to get there. Jessica had some explaining to do. I wasn't mad- well, maybe I was a little- but just mostly annoyed that she was making all these plans without even letting me know.
Of course, whatever irritation (and though I wouldn't even admit it to myself, anger) I felt, melted away as soon as I walked in, and saw the door to our bedroom open. Jessica had just walked out of the shower, naked, her body glistening from the beaded water across her skin. Her brunette hair wrapped up in a towel to dry. My eyes only momentarily saw her breasts and hips- becoming instantly consumed in by lust over the beautiful creature- before my eyes fell to her stomach. Though not yet evident to the world, she was pregnant, with our child. That knowledge tempered my irritation.
"Oh.. hi Shelly", she said, bending over to dry off her hair with the towel. "I take it lunch went well", she glanced up at me with a playful, knowing smirk. She knew what April and I had just did. She either knew me well enough to know I'd sleep with her, or April had already called Jessica to confirm it.
"You set me up", I said with enough playfulness in my voice to let her know I wasn't mad.
"You're right", she said, mocking my playful voice. "I was naughty, and I need a spanking”, she said, before falling on the bed, her ass stuck up in the air, wiggling as if tempting me to do something more than just spank her.
She made a playful squeal as I took a step towards her, before rolling over to protect her bottom. I merely fell on the bed beside her, as we both giggled. As our breathing slowly returned to normal, she looked into my eyes. "Okay", she started her confession, "she called me about a week ago, asking how to get back with you. And I may have given her some advice". She rose from the bed, and finished drying her hair, leaving me dumfounded on the bed. "Advice that seemed to have worked", she pointed out, as she opened her underwear drawer.
"We both know you love April", she said, pulling a pair of black, satin panties from the drawer, and pulling them up her legs. She held the waistband of the shiny material out, and then let them snap against her hip, as if punctuating her next statement. "And I know you love me. That's why I'm comfortable sharing you with her. And", she added, pausing a moment to have her telling smile crease her lips, "maybe you can share her with me?"
"Jessy...", I said, suddenly embarrassed, certain my whole body was blushing. She had said she was 'sexually experienced', but I never really thought about her with another woman. The thought of Jessica and April together, and also with me, was having a noticeable effect on me. My sister standing half-naked in front of me wasn't helping, as I suddenly realized my panties were left at April's apartment.
Jessica, of course, noticed too. "Calm down, Shelly". She said, fishing out a red satin bra, one with no padding, which let the nipple be visibly erect as she clasped it behind her back. "We'll have all night to play- just us girls", she said, as she got some shorts and a T-shirt. "But Jennifer will be home soon, and it'll be about an hour before Sarah comes to pick her up for her own sleepover". She swayed over to me, placing a hand on my lap, rubbing my inner thigh through my skirt, before kissing me. "But once she's gone..." She left the sentence trail off, as she turned away to finish dressing. But the sexual implications about what was going to happen tonight remained heavy in the air. "Now I left you plenty of hot water, so go take a shower, and get cleaned up...you kinda smell like cum and pussy right now", she smiled.
The doorbell rang right at 6:30, and my heart nearly stopped. I was sitting in the living room, not paying attention to whatever was on the TV, as April jumped up and ran to the door. She was definitely excited about her plans for the night. "Hi April, I'm so glad you could come", she then led April into our house by the hand.
"I wouldn't have missed it for anything", April said, handing her coat to Jessica. Beneath her beige overcoat was an outfit that I had only seen her wear once before, to mark our one year anniversary of living together. A sheer, silver dress hugged her hips and breasts tightly, ending mid-thigh, and accentuating every curve god gave her. The light cascading over her body gave the illusion of a goddess straight from Greek mythos, her dark hair falling in curls around her shoulders. There were no bra straps arching over her bare shoulders, and her nipples straining against the shiny material gave further evidence that she wasn't wearing a bra. With her before me, I was suddenly overwhelmed with why I had loved her, and why I still loved her.
As Jessica returned, I saw her in a similar light, and took note of what she was wearing. A simple cotton t-shirt, the outline of her red bra clearly visible, with her own erect nipples aching to be released. Cut-off jeans, easily showing as much toned leg and thigh as April, completed her lazy but attractive look.
As for me, having no idea what to expect for the slumber party, I was wearing a pink cotton tank-top, the Superman emblem- or rather, the Supergirl emblem- silk-screened on the front, while a lacy white bra held my breast-forms snuggly to my chest. I wore a pair of silky white panties underneath a comfortable pair of pink pajama bottoms, also adorn with the Supergirl emblem across the rear.
"I love your dress", Jessica said to April, snapping me out of whatever fantasy my mind concocted as I stared at the two beautiful girls in front of me. "I just hope you brought something a little more comfortable for later".
April smiled, the same playful grin I've seen quite bit. "I'm afraid I didn't bring anything else", she said, pretending to pout. "I was hoping to borrow something of Michelle's...unless you don't mind me running around the house naked".
The two vixens shared a small laugh as the noticed how uncomfortable I was at the situation. "Relax Shelly", my sister finally said. "We're just teasing you a little", she said, guiding April to sit next to me on the couch. "We just want you to be comfortable tonight. We've both had years of practice on how to use our wiles to make men uncomfortable, and a girl-girl team up is just unfair to you".
The rest of the night went much better. April indeed did change into my nighty, the purple silk one Jessica and I bought on our first outing to the mall. And I must say that it looked much better on her. Her full breasts filled in each cup, while the layered lace disguised her nipples to the naked eye. Of course, knowing where to look, or even openly staring as I was, there was no disguising her excitement. When she stood, the nighty was even shorter than the dress she had on earlier, ending right below her hips. And when she sat down, it rode up easily to expose the matching purple panties, my eyes falling to darkened shadows of her inner thighs.
I felt a pang of jealousy when I first saw her in my lingerie, and outfit I had only worn once, and only for my sister. But that feeling faded quickly once I saw how good she looked in them. Besides, my sister had taught me to share with my lover, and April was definitely my lover.
"Pizza will be here in about half an hour", Jessica said, interrupting the movie- some chick-flick with Rene Zellwinger- that no one was paying attention to. Instead, we just sat around and chatted, eating popcorn, and drinking diet sodas.
"Okay Shelly", April spoke up, looking me straight in the eye, "I've been thinking about just how good you look now", she started with the flattery, as I had a growing lump in my stomach. "So much so, that I think you should be the one to give the delivery boy his 'tip'", she said, as her hand cupped her own breasts, making it very clear what I was supposed to do.
"You want me to flash the delivery boy?", I asked, my feminine voice cracking slightly under the stress.
"Not exactly" my sister started, clearly a co-conspirator in this. "Every slumber party I've been at, one girl would always answer the door topless for the pizza. Look, we're not going to make you if you don't want to. This night is all about being comfortable as a woman. But as the only two people to see you naked, we can both attest that you have the goods to pull it off, not to mention what it will do for your confidence".
Both girls stared at me, waiting to see what I would say next. I truth, I didn't know. With my breast-forms, I was duplicating a healthy 38C chest, which easily held up against scrutiny from a passersby, even if all I was wearing was a bra. But topless, I hardly had breasts. Well, perhaps a little due to the hormones I was on, but it was a far cry from a real girls' chest.
"I'll do it", I heard myself whisper. "I'll do it", I said again with more confidence than I actually felt.
My bra and breast-forms were temporarily hidden between the cushions of the couch, while my Supergirl tank-top was draped over a chair that was visible to anyone who opened the door. I stood topless near the entrance, two $20 bills clenched tightly in my trembling hand as the clock from the kitchen again mocked me, drowning out all sounds but its infernal ticking. I looked down at my bare chest, seeing my own nipples harden with excitement despite the panic and fear that threatened to overwhelm me. Thanks to the hormones, I wasn't as flat chested as I had feared, as perky ‘A’ cups rose from my chest with every breath.
"I can't do this", I shouted in a panic, as I heard the car pull up to the driveway. I wrapped my arms across my chest as I ran for the bedroom.
It was April who stopped me, not so much as grabbing me, as just holding me. Her velvet voice then offered words of encouragement, "We're not going to make you", she said soothingly, while easing her embrace. "We said this was going to be a relaxing night for you, and we will honor that", she looked deeply into my eyes. "But I want you to know, that you are a beautiful young woman, and anyone would love to see you like you are now. And we promise you", she looked to Jessica to ensure that she was agreeing with everything she was saying, "that opening that door would only increase your confidence".
The doorbell rang, and I had only seconds to decide. Would I empower myself by answering, or live in a constant state of self-doubt?
I opened the door slowly, seeing a boy who probably was only a year or two younger than I was, holding two large pizza boxes, as he stared at the receipt. "That'll be thirty-one, twen....". The rest of his words became an unintelligible murmur as his brown eyes widened. I stood there, completely topless to the stranger's gaze, nervously letting him drink in my sexuality. Though my breasts were smaller than I wished, my erect nipples jutted out painfully from the small flesh from the excitement of it all. His eyes were transfixed on my young, budding chest. I had no idea which of use was more excited during the encounter, as I'm sure his heart was pumping blood just as fast as mine.
"Here you go. Keep the change", I said cheerily as I handed him the money, making sure to use my most feminine voice, as we awkwardly exchanged the money for the boxes. His hand momentarily brushed against my skin as I took the boxes from him. In that millisecond, I felt a surge of power, the same power I felt when I went shopping for earrings, while flirting with the clerk. It was the power of being a sexual woman.
I closed the door on the stunned young man, turning arround to smile at Jessica and April as they smiled back. "Thanks for encouraging me to do that", I said, suddenly at a loss for words. "That was....incredible".
April walked up, pulled the pizzas from my hands (before my limp arms dropped them on the floor). "It was our pleasure", she said, then kissed me. My head was swirling as her mouth pressed up against hers, our soft lips touching as lovers. She pulled her head away, a trail of saliva pulled between us before falling onto by breasts.
"We're very proud", my sister said, walking up to stand beside us, before planting a kiss on me too.
"That was hot", April said, watching my sister's lips tenderly pull away from mine. "I've always wanted to watch two sisters making out".
"How about it, sis", Jessica asked, peering into my eyes. I saw the fires of passion building behind her eyes, ready to consume her, me, and April. "Shall we give your girlfriend a show she'll never forget?"
The question was rhetorical. Whatever stories the two may have spun about what would happen tonight-a relaxing time watching movies, make-up tips, or merely chatting about the weather- we all knew where the evening would take us: Sex. I was the object of both of their desires, and we all knew what would happen.
Taking the lead, somehow empowered by the brief encounter with the delivery boy, I guided Jessica to the couch, holding her hand as we both eased ourselves down. April sat in the chair directly across, nothing obscuring her view from the once-in-a-lifetime incestuous display about to be performed. Her legs parted as she rest her hands on her knees, leaning forwards so as to not miss a single sight, sound, or aroma of the act about to commence.
Once we were situated, my sister took the lead, as I felt her hand gripping my budding chest, massaging it gently, the way only another woman could. Her head leaned forward, her lips parting slightly to invite my tongue inside. The invitation was quickly accepted, as my own lips parted as they touched, my tongue eager to find hers.
Her attention to my breasts did not cease, her hands were a blur of sensation, switching between her palm cupping them, to her fingertips tracing around my areola, to her thumb and forefinger gently pinching and lightly twisting my excited nipples. It was not a sensation I was used to, but my sensitive breasts ached for more.
"Kiss her again", April said, as if she were directing the sensual display. It wasn't until she spoke, that I realized that our lips had separated. I was so consumed with my sister's efforts on my breasts, that I didn't even notice that my head had tilted backwards, my mouth agape and my eyes closed, as Jessica's skilled hands teased every bit of excitement from my tits, while her lips danced across my neck.
Not wanting to disappoint our guest, my head flew down, my eyes and Jessica's briefly making contact, as I eagerly locked my lips to hers, my tongue again penetrating her mouth, all while my hands reached for her chest, wishing desperately to give my sister the same erotic attention she was giving to my breasts. My hands fumbled over her t-shirt, mauling her like I was some high school boy getting to second base with his girlfriend for the first time. That was no way to treat my lover. I forced my hands to slow down, emulating her moves in slow, purposeful actions, even through her shirt and bra.
"Take her shirt off", April's voice was dripping with lust. I opened my eyes for a moment to see her in the same posture, licking her lips as the two lesbian sisters devour each other in a carnal way. I had somehow expected her to be leaning back, two fingers in her pussy trying to get herself to cum. I admired her self-restraint. She definitely wanted to savor the moment.
I reached down for the bottom of Jessica's shirt, and pulled it up and over her head. Her hands stretched above her body, causing her full breasts to jut out, even contained in her thin bra. I tossed the shirt to April, who caught it before casually resting it over her leg.
My eyes were focused solely on my sister's breasts, as they heaved heavily with each labored breath she took. The thin, silky material of her bra did nothing to hide her excitement, as her nipples strained erect.
I heard an unmistakable moan of excitement from April, clearly enjoying the show we were performing. "Bite her nipple", she directed. My sister gently pulled her hand from my chest, then pulled the right cup of her bra down, exposing her perfectly pink nipple to me.
I paused for only a moment to consider it. Biting was painful, and now having my own sensitive nipples now, I could imagine how painful it could be there. A gasp escaped my sister's lips as my mouth contacted her breast, clearly excited by the prospect. With a little suction, I pulled her nipple into my mouth, and slowly, carefully, closed my teeth around it, applying increasing pressure. With every moment that past, my sister seemed to be in ecstasy.
"Open your mouth, show me your teeth biting your sister's tits", April was being far more than a passive spectator at our show. She was commanding, daresay dominating. I had never seen her like this. Of course I did as I was told.
"Good girls", April cooed, watching us. It didn't matter that she was younger than either of us: Right now, she was in charge. "Stand up", she ordered me, as I reluctantly pulled my lips from Jessica's breast. "Jessy, pull your sister's pants off. Time to see how she looks in just her panties".
Jessica looked up at me from the couch, our eyes locked, as her hands reached for the waistband of my pajamas. With her thumbs tucked in, and careful to only hold the pants- not my panties- she pulled them down my smooth legs. With all the excitement, my clitty was hard, the tip easily protruding from the waistband, with a glistening trail of precum from the front of the satin panties to the hole at the tip. Jessica inhaled sharply, the aroma of the perfume I wore mingling with the smell of sexual anticipation assaulting her nose.
"God, she has a beautiful clit", April moaned in appreciation upon seeing my erection. "Don't you think so, Jessy", she asked.
"It's the most gorgeous clitty I've ever seen", she replied, her eyes focused on the seven inches I barely had contained by white panties, as it pulsed with each heartbeat I had.
"Pull down her panties, but just enough to release your sister's clit", Jessica obeyed April's command, eagerly releasing me from the satin covering my bulge. "Now", April started slowly, standing up to finally join us, "Take your sister in to your mouth". As she spoke, she crossed her arms in front of her, grabbing the hem of my lingerie that she was wearing, and pulled it off of her in one smooth motion. "But don't you dare let her cum", she warned, placing a forceful hand on my chin, turning my head to pull my face to hers. “That belongs to me tonight”.
It was an odd, but arousing sensation. The moment April's lips touch mine, Jessica's mouth enveloped my clit. Her warm mouth and supple lips slid over me as easily as my own lips parted for April's penetrating tongue. I felt completely helpless as her tongue slid in and out of my mouth, while she fucked my lips with her tongue. All the while, Jessica was doing the same thing to her own lips and my clitty.
I felt an overwhelming sensation of powerlessness. Even if I wanted, I couldn't fight back against April's commands. I would do whatever she wanted, eager to please my mistress, girlfriend, and lover.
She took a firm grip of my wrist, and placed my hand gently against her flat stomach. "You're going to put your cum inside of me", she whispered into my ear. "You're going to impregnate me", her sultry words tickled my ears, as her hand was slowly pushing mine into the waistband of the silky panties she wore, until my fingertips touch her triangular patch of hair on her mound, and I could feel the heat of her thighs. "You're going to knock me up tonight...bitch".
I have no idea why being called a dirty word excited me like it did. Perhaps I was caught up in the role of being a submissive little girl, that having my girlfriend call me names filled me with a previously unknown passion. Maybe it was the way she said it, being the dominate one tonight. Never before had she been sexually dominating. Maybe as I filled my role as a girl, she would fill hers as a strong man.
I next felt a quick slap against my ass, as April's hand came down hard, "did you hear me slut?" she asked rhetorically, again calling me a dirty word that filled me with lust for her.
"Yes, mistress", I cried out, feeling her hand gripping my butt, her nails digging into the sensitive flesh. Jessica's efforts on my clit intensified as she heard my submissive voice, while her hands trailed up my body to once again play with my small chest.
"Good girl", April smiled, slowly releasing her grip on my ass, and staring into my eyes while pushing my hand further into her panties, further between her thighs. I felt her body shift, as her legs parted, giving me access to her moist lips. "Make me cum", she commanded.
My fingers were quick to obey, blindly parting her lips beneath the satin panties as my fingertips searched for her sensitive clit. My other hand reluctantly pulled Jessica from my throbbing clit. Her efforts were almost too good, and I didn't want her to get in trouble for making me cum too quickly.
"Want to take your shorts off, sweetie", April invited her to get as naked as the rest of us. It was clear in her tone that I was the only submissive tonight, as she spoke to my sister as a lover and equal. "Then you can have her other hand if you want it", she then suggested.
Jessica stood, pulling herself to her feet. She turned around, standing very close to me, as her fingers undid the button and zipper of her shorts. Bending at the waist, she slid her shorts down, the material dragging over the length of my exposed and slick clit. "Ahhh", I couldn't help but to moan at the feeling, replaced nearly instantly as my clit rested lovingly between my sister’s bare ass cheeks.
"I should have known that you wouldn't wear any panties", April commented on my sister's nakedness. "That wasn't part of the deal", she said through gasping breaths as my fingers worked within her slick folds.
"Shhh", Jessica chided April. "She already thinks we're plotting against her", we all smiled at that. I knew about Jessica and April talking, but had no idea what subjects they covered. When April invited me to this slumber party, all I knew was that they had planned it together. Evidently they had a lot of plans for me.
"Just relax little sister", Jessica comforted me, while also guiding my other hand to her waiting pussy. She too parted her legs, "this is going to be a momentous night for all of us", she said, right before she gasped as my fingers brushed against her clit.
With a lover on each side of me, my hands feverishly trying to satisfy them both, we kissed. Admittedly, it was awkward trying to keep my fingers dancing on their clits, as both brought their bodies close to me, and our cheeks touching. But we kissed, my tongue simultaneously touching and playing with April's and Jessica's, while they fought each other to play with mine in an erotic display.
A strong and forceful hand gripped my wrist, as April pulled my fingers away from my sister's drenched pussy. With her grip, she held my fingers to Jessica's lips, and waited with an expectant look on her face. Jessica took the unspoken command from April, pulling my fingers, dripping with her own arousal, into her mouth, closing her eyes, and sucking them as if it were a cock.
April and I both excitedly watched my sister's head bobbing up and down on my fingers, that moment before were in intimate contact with her pussy. The aroma of her sex on my fingers was overpowering all of our senses, as we all watched her erotic display.
Eventually, April grabbed my chin to pull my eyes towards her, forcing my full attention on her. I heard her voice clearly in my head, as her sensual lips mouthed the words "fuck me".
She eased herself to the floor, pulling me on top of her, my fingers slipping from Jessica's lips. I was poised above April's petit frame, my aroused clitty bouncing with each heartbeat. I looked down between us towards my own chest, seeing for the first time, the proof that the hormones were working, as my own breasts pulled from my chest. In the moment, I had lost track of Jessica.
"I said fuck me you whore", April bellowed softly from beneath me. A raging fire in her eyes made it clear to me that this was a command, a command given from a mistress to her submissive. I strangely relished the idea of being her sexual toy.
My clitty was hard, harder than I can ever remember it being. It took only shifting my hips downward to align myself at April's pussy. With a small thrust, my tip became engulfed in April's warmth. She has ordered me to fuck her. Not to make love, not to have sex, but to fuck. A submissive never questions her orders. And with that final thought, my hips took over, pushing the length of my clitty into her in a single thrust, and withdrawing nearly all of it a second later. I was fucking April, as she had commanded.
I guess it's hard to stay dominate while you're lying on your back, legs spread wide, as a you're being fucked, all while moaning in loud, unintelligible grunts each time your pussy is penetrated. Mistress April finally succumb to the pleasure, as her legs entwined with mine, and her hands wrapped around me, firmly planted on each of my ass cheeks, kneading and playing with the globes of flesh. "I love you, Shelly", April moaned between grunts. At that point, she became just April, my girlfriend and lover again.
I was close, very close to giving April all the cum she craved, hopefully impregnating her as she had demanded. A few more strokes and my load would be pumped into her waiting womb. Just a few more thrusts and my 'forever time' would envelope me.
A shadow passed over the living room as I realized that Jessica had gone somewhere and was now returning. I felt April's forceful hands on my ass again, her efforts stopping my thrusts, denying me my orgasm at that moment. "I love you, Shelly", Jessica whispered the words into my ear, and April held me in place with her hands. "You can say no if you want", she whispered to me.
I was confused, but that only lasted a moment. That was when I realized what exactly the two vixens had planned. With April’s hands on my ass, she took a firm grip, and spread my cheeks apart. And with a surprisingly warm hand, coated with what I instantly knew to be lube, I felt Jessica's touch caress me in an extremely intimate way. Jessica was about to take my virginity.
I was filled with a panic, my whole body tensing. It was a scary proposition, one that usually doesn't just get sprung on someone, especially not in the middle of sex. A million thoughts flooded my head, everything from "will it hurt" to "will it make me closer to being a real girl". Truth was, I have thought about it before, but decided I was going to get used to being a girl first, before broaching the subject with my sister. I guess she had another plan.
Though I hadn't seen exactly what Jessica had on, a small glimpse out of the corner of my eye told me that it was purple. No clue to its length or girth. But I did know that Jessica loved me, and wouldn't subject me to the toys seen in most videos. After the myriad of questions in my head were answered in mere seconds, I forced myself to relax, and nodded my head.
A gentle kiss was placed at the nape of my neck, as Jessica knelt behind me. I felt her body push against my back, as the toy she wore rest between the well-lubed cheeks April held open. Despite my courage, I still tensed as I felt the tip touch my rosebud. Jessica gave me a few strokes up and down between my cheeks, the toy becoming coated with the slippery substance. I felt the excess lube slowly dripping down, tickling my scrotum.
What felt like forever, but at the same time not long enough, Jessica's hand reached down between us, angling the toy down to line up with my rosebud. I forced myself to relax. And with the patience of a generous lover, Jessica slipped inside of me.
"Relax", April offered her encouragement, while my clitty remained lodged inside of her. "Take it like a good girl", she said, some of her dominating personality returning to her.
Inch after inch of the hard plastic toy violated and stretched me, as my sister took my virginity with her strap-on. There was pain, I'm not going to lie about that, but that was easily tempered by the love I felt from both my lovers. I closed my eyes tightly as the toy crept into me, stretching my tight hole with its enormity and length. It seemed to go on forever, until I felt her thighs touching my ass. It filled me completely, its entire length. Jessica paused there a moment, letting me become accustomed to the intruder.
Then I felt it retreat, as my sister puller her hips backwards. This sensation was just as foreign to me as the initial penetration. Not unwelcomed, just different. Inch after inch was pulled from my virgin ass, filling me with conflicting emotions. One wanted the intruder gone, so that the ache I was feeling would ease. Another, more primal and carnal, wanted it back, to give myself completely to my sister.
Another forward push from Jessica's hips, and the carnal feeling prevailed. My tight ass was stretched and filled again by the monstrous toy. Blissfully, my sister was slow and gentle, giving me ample time to adjust to her inward thrusts, holding it for only a moment, before retreating again. This pattern repeated until we both felt comfortable with an increased pace. I didn't even realize that I had started to moan as my sister fucked me.
"When she thrusts into you", April spoke, my eyes flying open to see her speak, "thrust into me". And with timing, I felt Jessica begin to push her hips forward. And as her strap-on sunk into me, I drove into April, as the two of us moaned at each other. Taking the queue, as Jessica pulled out, so did I.
And that's how the three of us made love. As Jessica's toy penetrated me, I penetrated April. And as Jessica withdrew, so did I. With effort, and synchronizing our timing, I was soon close again to my climax.
"Fuck her ass while she fucks me", April yelled at my sister, the excitement of her own impending orgasm clear in her voice. "Bury your cock into her tight ass. Make her cum inside of me".
"You like that little sister", Jessica asked as we both thrusted forward into our lovers.
"Yes", I managed through clenched teeth, thoroughly enjoying the sensation of my clitty inside April, while my sister took my virginity.
"Then cum, you dirty slut", April ordered, screaming at the top of her lungs in rapture. "Pump your cum into me".
There's a moment of sexuality we all experience, between achieving one's orgasm, and the infinitesimal time where nothing could stop you from doing so. I call it a 'forever time', where dreams and passion overwhelm you in an instant. My hips thrusted forward into April's waiting womb, while Jessica's toy likewise stretched me. Where as I held my pose, ready to give my seed to my lover, Jessica continued to pump in and out, continued to fuck me. And in my 'forever time', Jessica must have thrusted and withdrew a hundred times, before April received what she desired.
I arched my back, threw my head backwards, and, pressed my small chest into April's. The sweat between us became an erotic scented lotion, glistening off of our naked bodies. Jessica took a strong grip on my hips, holding her strap-on inside of me as I started to cum. My eyes opened to see April's face as her own 'forever time' neared, her crimson lips pursed to call out my name.
With a force I had not expected, and a soft moan I managed instead of a grunt, I came. I felt spurt after spurt of my cum jet inside of April's welcoming pussy. Convulsions wracked through my body, feeling as if an electrical charge began from the toy in my ass, tingling up my spine, coursing across my flushed forehead, through my chest, before finally being release into April from my clitty, who convulsed as her own orgasm overtook her.
We stayed like this for moments afterwards. My clitty softening inside of April's womb, and with Jessica's toy thrust deeply into my ass. We were all panting, struggling for air, in the afterglow of the phenomenal climaxes.
Eventually, and slowly, Jessica withdrew her strap-on from my no-longer-virgin ass, then stood before of me. There was something erotic and perverse about seeing a beautiful girl with a strap-on. And far from the monstrous intruder my mind had envisioned as it penetrated me, the purple toy was about six inches long, and the diameter of a highlighter marker. She later assured me that it was the smallest strap-on the store had.
I pulled out of April, a trail of cum oozing from her pussy between her thighs, to eventually stain the carpet. Without a moment's hesitation, Jessica knelt beside me, before her head became buried in April's crotch. She hungrily lapped at the pearly cum flowing from the young girl's lips, flicking her tongue against April’s clit, consumed with the task of tasting both of our cum in a sensual cocktail. And to bring the girl to another orgasm.
Had I not just climaxed moments before, seeing my sister eating out another girl- my lover no less- would have pushed me over the edge. April was clearly enjoying the attention, as her already labored breathing became desperate gasps for air, as another climax neared. Twice in as many minutes, April received mind-blowing orgasms from sisters.
We each shared a kiss with my sister, smelling the raw sexuality on her breath, and tasting it coating her lips. One thing my sister had gotten right: This was a momentous night, that none of us would ever forget.
It was about an hour later. We had showered, and then returned to the living room. The overwhelming aroma of sex penetrated our senses, but no one seemed to mind as we ate some pizza, and continued ignore the movie while we chatted.
April confessed to having dominating desires, but was always afraid Michael wouldn't let her play them out. Michelle, however, might actually like it. It was actually Jessica who encouraged her to play out her fantasies tonight. I assured her, I would be her submissive bitch anytime she wanted. It was a promise that would get me into some naughty trouble a few years later, but that's another story.
And at some point, our future, the three of us together, came up. I didn't know what to say. I was happy with the way things were right now, having two lovers, and knowing both loved me. The idea of marriage came up, and while it wasn't dismissed, we all agreed that I needed more time as a woman before I became a wife. Even Jessica liked the idea of April and I getting married, so long as we invited her to the honeymoon.
Ultimately, we decided to play things by ear. April and Jessica would both help to make my transition as seamless as possible, and both had agreed to share me equally as a lover, and to enjoy the occasional threesome together (oddly, I wasn't even consulted as they decided this, but I was happy with the outcome).
Finally, in the wee hours of the night, we all decided it was bed time. The three of us tiredly stumbled to the large bed, and fell on to the comfortable mattress. Jessica pulled open the covers, as we each slid underneath, the heat of our naked bodies warming the sheets. As I lay there, sleep creeping into my head, I felt my lovers slip in close to me, holding me in each of their loving embraces. A quick good-night kiss was shared, before we each succumbed to the dreamscape of our imaginations.
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