Shawn and Mitchell came back into the room. Shawn carried a bag with him and Mitchell came over to me with thick silk straps over his arm. Shawn put the bag down and went over to help Mitchell as he climbed up on the bed and marked out anchor points in the ceiling then secured some heavy duty metal anchors with thick screws above the bed. The two of them carefully threaded the silk straps through the loops in the anchors and tied off the very ends, dropping the rest of the strap down beside me.
Some of the straps were attached to a single anchor in the ceiling and some were attached to two anchors. I learned why fairly quick. One strap was positioned beneath my head, both ends were secured to anchors. Another went around my back and under my arms, it was also secured to both anchors in the ceiling. A third strap was guided under my mid-back and attached to both anchors in the ceiling. Then a fourth double anchored strap was placed beneath the upper part of my ass/lower part of my back.
None of the straps were pulled tight yet, they were just placed where they were needed. Once all four were in place, the two of them worked together to elevate my head, maybe two feet off of the bed. The same was done to the rest of the straps until I was hovering with red silk straps supporting my body.
Another set of anchors placed further out from the first set had straps with single attachments. The ends of which were secured to my wrists, thighs, and knees. The ends of those were tightened until my arms were stretched taut out to either side of my body, my thighs were lifted and separated and another strap secured my knees to hold my legs in position even with squirming.
There wasn’t a single part of my anatomy that wasn’t available to them and I couldn’t see them from the angle they secured me. My head was slightly lower than my hips, but only enough to make it difficult for me to lift my head to see them. They started together, the differences in their touch was obvious to me right away. Shawn rubbed my clit slowly and gently, just the way I liked and Mitchell’s fast and repeated prodding of my g-spot was such a stark contrast that together they brought me to a quick and powerful orgasm, causing my body to tremble and squirm against the silken platform they displayed me on.
With my cunt still contracting in pleasure, I felt something firm, but with a soft covering, press against my opening. It felt thick and I tried to pull away slightly as it felt significantly too big to go inside of me. Mitchell climbed up on the bed and looked over my face, “It’s not as large as it feels, I promise you,” he said as he stroked my cheek.
I nodded and he moved back down to my lower body, his fingers spread my cunt as wide as it naturally went and Shawn tipped the thing at my opening and very gently eased that bulbous first two inches into me. My hands were clenching into fists and I cried out as my body fought the width needed for this. I know Shawn wouldn’t allow something that would be likely to cause me damage, so I knew it only felt like a fucking giant troll dick, but it was still bigger than anyone I’ve ever had in me before, without question.
I took a deep breath and Mitchell rubbed my clit as he praised me, “That’s it, we’re just gonna go slow and in a few minutes you will be begging us to go harder,” he said softly.
Shawn pulled it back to the head and spread lubricant generously over the object and eased it back into me. It rubbed firmly along my upper vaginal wall and, while it could have been an orgasm — the feelings of tingling and relief were there even without any of the tremors and full body involvement — I’m pretty sure I pissed myself as it went deep into me.
Mitchell continued rubbing my clit, his thumb and forefinger caressing either side of the sensitive flesh as my boyfriend continued to push and pull a firm, rubbery coated object in my pussy. Then I noticed Shawn holding very still as Mitchell’s other hand rubbed around my opening before Shawn began pulling the thing from me. The head of it pulled at my opening and I whimpered as Mitchell spread my cunt and Shawn tipped the toy until he was able to pull it free of my body. I felt the coolness of lubricant being spread liberally inside of me.
The object was gently reinserted in me and this time Mitchell had control of it while Shawn licked and sucked on my clit. Mitchell wasn’t as gentle. His thrusts were deep and slow, tipping it so the head rubbed along my g-spot and up along the forward wall of my cunt with force. I moaned and he pulled it back and pushed it in again, ensuring I felt every fucking millimeter going into me.
Mitchell’s thrusts became a little faster, Shawn moved up my body and began sucking on my breast as he rubbed my clit in little circles with a lot of pressure behind it. I wanted to move, I pulled at my wrists and my thighs tensed up as my stomach clenched. Mitchell’s thrusting became faster, going deeper than Shawn had pushed me. My toes curled and I reached an almost violent orgasm, this time I knew I’d squirted, as my whole body convulsed and arched in pleasure.
Both Shawn and Mitchell stood between my legs and admired their work as Mitchell worked the dildo back out of my cunt. I felt Shawn’s tongue inside of me first, he licked deep and held me open with his fingers. When he pulled back I felt Mitchell’s fingers pushing into me and holding me open so he could get a few deep licks in while my cunt was still contracting.
They repeated the motions they’d gone through with my ass, each had two fingers in my cunt, pulling and pressing me open as they stroked each other’s dicks. They had a much smaller target this time. As much as their goal was to cum directly on my cervix, the toy needed for such significant stretching would rip me the fuck open and they weren’t in this to hurt me.
They settled with alternating ropes of cum down my vaginal canal then wiping their tips off into my hole together. They pushed their heads together and into me slightly but I whimpered and instead of stuffing my cunt with two dicks that were significantly sized for me individually, they just held themselves at my opening until I closed up around them and my body forced their heads out of me.
I was sweaty and panting when they lowered me back down to the bed. Mitchell brought the toy they’d used on me over so I could see it. While I was imagining it being the size of a burly adult male fist, it wasn’t anything near that. It was about seven inches long and had a circumference around six inches. Not that big, really. If we were talking diameter, it would be around two inches thick.
Mitchell grabbed the bag that Shawn left on the floor by the bed and pulled another toy out of it. This one was almost double the length of the first one and a good two and a half inches thicker. My stomach clenched at the thought of how much that would hurt.
Mitchell laughed at my reaction, “We aren’t going straight to it. There’s an assortment of sizes in here to work you up to this one. It’s modeled after a real cock that we are going to introduce you to in a few months. For this encounter it would only be myself and you, Evelyn, as I’d rather not subject Shawn to this man’s cruelty. She won’t leave my sight and he won’t harm her, but he will harm me to have her.”
Shawn looked at Mitchell, “How hurt are we talking?” he asked.
“It’s just a scene, but I will leave injured, bruises, a mild concussion is likely, there is a risk of broken bones but they typically don’t go that far. She will have sex with him and a few of his men. Your share together would be four hundred and fifty thousand dollars and I would take three hundred thousand as I’m the one taking the brunt of the abuse this time. No harm would come to her. They are extraordinarily delicate with the girls, it’s the men with the girls that they take pleasure in torturing and ridiculing.”
“Why are you volunteering to be the one they abuse?” Shawn asked.
Mitchell smiled, “Because you would fight much harder than me and you would likely leave much more seriously injured than I will. It’s a six hour party worth two hundred and twenty-five thousand dollars each and you don’t even have to attend, Shawn, you simply have to trust me with Evelyn’s safety.”
“What if I can’t get to where I can handle a cock that big?” I asked.
“I would tell him ahead of time. He might still try, to make sure you aren’t lying, but most likely he will just finger you and get you to suck him as best you can if you can’t take him vaginally or anally. I just need to know you’re both on board to try before I make the arrangements. Once they are made, we can’t back out or we will have to pay them for wasting their time,” Mitchell said.
Shawn looked hesitant but I looked at Mitchell and nodded, “I’m down to work on getting there,” I said as I looked to my boyfriend.
He ran his hand over my cheek and nodded, “If she is then I am too.”
Mitchell smiled, “Excellent, by the time this party is over you two should have a nice little nest egg built up for yourselves.”
They cleaned me up and we all said our goodbyes. The next few weeks consisted of us meeting Mitchell and his friends on Friday nights. Mitchell didn’t come home with us after every time, but when he did he would test me to see which size I could handle and to see if Shawn was holding up his end of the job in training my cunt to stretch as needed. It took me six weeks to manage the ten inch 3 wide dildo. I was struggling with going up from that one.
Mitchell tried at the eight week mark and I managed to take the head of the ten/three and a half with a lot of lube and the use of a wedged pillow and restraints to keep me from moving away from the toy. At ten weeks I could get halfway down it. I was ready to give up on the idea of ever fitting the monstrous last dildo inside of me. Our sessions used to end with Shawn wrapping me in his arms and holding me close to him, lately they’ve ended with me being outright exhausted with Shawn holding an ice pack to my cunt.
At twelve weeks I was able to get the size before the final fit to the halfway point, twelve/four was my current max and I wasn’t even able to take it fully. I needed to get another three quarters inch of width stretch. Another six weeks and I might have managed to make myself stretch like that, but I had two. Mitchell got Shawn to kiss me as a distraction while he worked on rubbing and stretching me to take the thickest point of that dildo, just to see if I could. It hurt and I cried out, though it was muffled through Shawn’s lips.
Mitchell managed to get the dildo mostly in me without tearing me, but he bottomed out in my cunt at the ten inch mark and it hurt inside when he thrust it fully into me. He was trying to get me accustomed to the feel of the pain of having my cervix pounded repeatedly and after a while I did, even finding myself in the throws of a full body orgasm when he rubbed it firmly against me.
When they finally removed it from me I felt like I’d given birth or something. The pressure and fullness eased and it felt like my fucking organs were put back the way they were supposed to be instead of being hijacked and shoved apart by a massive dick. Both guys could almost fit in my cunt together now. They tried, just out of curiosity, but I wasn’t capable of that just yet.
Maybe after the party I would be.
By the thirteenth week I could take the head of the largest dildo in my cunt. It only took daily fucking for a few hours at a time over the thirteen weeks to get me there. Oh, and this whole time they’d been working my ass too. I somehow had a much easier time stretching my ass than my cunt. I was starting to worry things wouldn’t feel right with Shawn after all of this. I used to think he had a big dick, now I’d wager his dick was about average width and slightly above average length.
Shawn pulled out the dildo the night before the party, but I told him no. I would either handle it tomorrow or I wouldn’t one more night of forcing my cunt to open up wasn’t going to make that much of a difference. Instead, I just wanted a night with him. He happily gave me what I wanted and let me ride him for over an hour, giving me multiple orgasms and him two over the course of an hour.
Things with him still felt amazing. I didn’t feel like I was stretched, but they didn’t feel like they did initially either.
I looked at him and finally blurted it out, “Was this a mistake?” I asked.
“I don’t like it. But I don’t own you and I’m not going to put restrictions on you. I love you and I just want you happy,” he said.
I shook my head, “I don’t mean that, Shawn. I mean…the stretching, is it changing how I feel to you?”
He smiled and kissed me, “You feel just the same as you did the first time I talked you into letting me fuck you, Evie.”
I scowled, “I doubt that…I was a virgin before you fucked me that day at the office. It doesn’t feel the same to me,” I said softly.
His jaw clenched and he looked me over, “Is this going to hurt our relationship?”
My hand slid over his jaw, “I hope not. I think I want to stop after this party. I want my body to go back to normal, I feel gross,” I said.
“Good, I’ve hated this, it was only ever supposed to be me fucking you. I like how happy you seem getting fucked by Mitch, but I miss you just being mine, Eve. But being perfectly honest, you’re not gross at all. You’re amazingly beautiful and I’m in awe with the entirety of your body,” He said just before kissing me.
“Listen, I was going to wait, see if you still wanted to be with me after being with this rich god of a guy…but I don’t think I want to wait,” he said as he reached down to the floor and retrieved his pants then pulled a small ring out of his pocket.
“Evelyn, I have been in love with you since you spilled wine on me when you thought I was your ex at that work party. The look on your face when I turned around was just amazing. Most women would have been horrified at realizing they’d made a mistake. You just looked at me, smirked, and said ‘Work harder at not looking like an asshole,’ then turned around and left. I knew then that you were someone I wanted to know,” he said with a laugh.
I put my hand over his mouth and stopped him from continuing, “If it makes you feel better, I went to the women’s room and cried for half an hour. I’m not as different as you think.”
He pulled my hand away from his mouth and kissed me then looked me in the eye, “You’re beautiful, daring, adventurous, caring, unbelievably intelligent, and you are exactly the woman I thought you were after that encounter. And now I want to know if you’ll be the woman at my side for the rest of my life,” he said.
I kept my gaze on him, not even looking at the ring as I nodded, “If you’ll have me,” I said softly.
He kissed me and I closed my eyes. One more night and it would be just the two of us. When I opened my eyes I tilted my head and pulled my lips away from him, “I think I’d like to move in with you fully when my lease is up,” I said.
“I think I’d like us to move somewhere together instead. Not you moving into my house or me moving into your apartment, but us moving into a home that’s ours. Would that be okay with you?” He asked.
I nodded, a smile on my face as I kissed him, “One more event then I’m one hundred percent yours, Shawn.”
We snuggled up together and quickly fell asleep. This Friday would be the end of it. I just hoped Mitchell didn’t give us any shit for ending it. I wanted to put this adventure behind us and the only thing in our way was an old man who liked the chase as much as the game. But, he’d grown to care about both of us and I imagine he wouldn’t try to stand in our way.
We’d find out soon enough.
Source: reddit.com/r/Erotica/comments/ii2npn/strangers_on_a_train_part_four_vaginal_stretching