Between a Rock and a Hard Place

Without anymore thought about it, I dipped a finger inside of her and realized that she was even wetter than before, and her juices were literally dripping down her legs! As soon as I touched her, she started to moan loudly and started bobbing her head faster. It felt so good, but I still needed a bit more time, and I think she was starting to realize it.

Right then, I was surprised to feel something bump against my hand. At first, I thought it was her hand, but when I felt it, I realized it was definitely not a hand, but someone else's cock coming through the hole!

Immediately, I moved my hand and grabbed the cock. I didn't want it getting anywhere near her. As soon as I grabbed it, I realized two things. The first was that it was sheathed in a condom, which made me somehow feel better, but the second was that it must be huge, or at least substantially larger than me.

Jenn hadn't realized what was going on yet, and I didn't want her to scream, so with my other hand I took her mouth off of my cock and said, "ok, I need you not to freak out, and to listen to me, ok?"

"Ok..." she said questioningly.

"Alright, promise you won't scream" I said.

"Ok, I promise. What is it Jason? Is it a spider?!" she said with fear in her voice.

"Uh, this is really weird, but I think there is a gloryhole behind you, and I have some guys dick in my hand" I said.

"What?!" she yelled, starting to get up.

"Just stay still for a second and I'll show you" I said as I put a hand on her shoulder to keep her where she was.

With that, I pushed the cock back into the hole it came from and repositioned it on top of her butt. As he pushed it back into our booth, we both realized that it was enormous and jet black. When I say enormous, I mean it looked like the larger vibrators we had seen, maybe 9 or 10 inches long and a lot bigger around than me. It was also wrapped in what must have been one of those magnum sized condoms, which covered it well, but was surprisingly maybe a little too big still. Since it was wrapped up, I actually didn't feel that bad about it touching her, and apparently neither did she since she didn't just jump away.

"Wow!" she said looking back, "That thing is huge! Look how big his head is!"

"Yeah, it definitely is." I responded looking down at him. His head flared out a lot and was abnormally large, maybe the size and shape of a small plumb. "How does something like that fit?" I said.

"Not sure..." she responded. "It definitely would have a hard time getting in me, and if it did it looks like it's not shaped to come out very easily if it could even fit in."

"What do you want to do now?" I asked.

"I don't know he's wearing one of those big condoms, so it covers his whole length. Do you think maybe we just let it sit on top of me like that for a minute? This is so weird, but the situation is actually turning me on even more, and the weight and heat of it feels good" she said with a bit of a wild tone to her voice.

"Ummm, ok" I said reluctantly.

I had done some wild things before, but this was by far the wildest. Letting my girlfriend suck me off while she had some other dude's giant dick sitting on her ass.

With that, she started sucking again, this time more, harder and faster. The only problem was that this time, I wasn't looking just at her ass, I was looking at a monster cock sticking out of the wall and sitting on her ass, and I was having a harder time getting hard like this.

Just when I thought I wasn't going to get hard at all, I noticed she started moving her ass up and down massaging the bottom of the cock between her cheeks. When she did this she started moaning again. All of it put together just started to make me hard. It was so weird, but she was making me feel so good with all those moaning vibrations. I reached down and started massaging her clit again, and she started to respond pretty quickly. She started moving her hips faster and moaning louder.

Even with the additional stimulation, our new friend was starting to get soft. It started to scare me a little bit because he was wearing an extra large sized condom and as he was getting soft so he was shrinking out of it a little. But this point she was starting to get me hard and I didn't want Jenn to stop what she was doing. So instead of thinking it through, I took the shrinking monster cock and pushed it back into the hole again then down between her legs where I thought that he may get more stimulation from her legs. The angle they were at lined him up perfectly with her pussy, but he was still softening, and far too big to easily slide into her. I think he rubbed right against her clit as he pushed back into our booth though.

I leaned up and put both hands on her back for a second and said "hey babe, he was starting to get soft, so I put him between your legs for more stimulation, is that ok?"

"Oh god babe, I'm so turned on right now, whatever you want!" she said with a little jump in her voice as she felt him rub her clit with top of his softening cock.

"Maybe you could squeeze your legs together a bit to harden him up again?" I asked.

Without saying anything, she lifted the leg on the floor up onto the bench as well and squeezed her legs together and immediately moaned.

"What was that?" I asked.

"Ohhhhh, he's pushing in and out now and hitting my clit with the ridge on his head as he moves. With my legs squeezed like this, it feels really good." she responded. "But it also feels like his condom may have moved. Can you tell any difference?"

I reached back under her, and could tell he was getting hard again. But he was trying unsuccessfully to get inside of her and was pushing past the hole just far enough to get to her entrance. So when I reached to feel the condom, I could only feel about an inch and a half past the head of this monster cock. It was definitely still covered, but when I felt closer to the front, the head wasn't engorged like it was there was a good bit of empty wadded up condom at the tip. It must have slid up some before he got hard again since the head had shrunk down so much. Since I could just feel the tip and another inch, I couldn't tell exactly how much was uncovered. I tried to move the condom to make sure it wasn't going to slide any more. It did move a little bit, but as soon as I touched him, the head started to get big again and the condom tightened around it, trapping it in place. So as far as I could tell, at least the head and another inch or two was covered, and that was more than what was touching her.

"It did move a bit, but I think it's fine. I can't feel it all, but the head and a mit more is definitely covered" I told her.

"Just the head?" she said.

"Hold on, let me make sure," I responded.

As I was trying to feel further, I thought she would like a bit more pressure on her clit so I reached and pushed the top of his cock against her mound and rubbed it against her outside. He kept trying to slide back and use the pressure to slide inside of her, but he was so big that even with the extra pressure he would press against her entrance then just slip forward and hit her clit. That giant head was a lot squishier than I thought it would be. It seemed like it was softer at the top and hardened at the bottom. Maybe to let it get in easier I thought to myself, but didn't say anything to her.

She started moaning louder and rocking up and down on this giant cock involuntarily. At the same time, he started moving in and out of the hole a lot faster while she started to stroke me at the same speed. It was hard to tell since I wasn't actually seeing it, but I thought for a second that I felt a bare part of his cock come through the hole an inch down from the head and catch the ridge of the condom on the hole when he pulled back out again. I couldn't tell how much was now unsheathed, but it couldn't be that much more and I figured since this cock was huge, especially that head which was all that was touching her anyway it would be fine. My brain was starting to get fogged up from what she was doing to me, so I just let it go for a minute and told her "I think he's covered fine."

"Okayyy... Good... cause that feels really gooood..." she moan, "I like the pressure of his head at my entrance. But don't let him push too hard, he's starting to kind of stretch me open a little bit and I don't want that giant head even starting to go inside of me, even with a condom on."

"It's huge, do you really think it will be a problem?" I asked as I pressed the head right against her entrance as he pushed forward a little bit. Even though the head was huge, it felt like the squishy part of the head sank in a bit, but then slipped forward and slid down the front of her pussy harmlessly.

She gave a little moan and rocked forward away from him and said "If you keep letting him push at my entrance, eventually he'll open me up."

I just looked down at her blankly for a second as I was really enjoying teasing her.

She shot me a sharp look followed with "I'm a girl, I'm turned on and soaking wet, and you're pushing a erect penis into my vagina. What do you think will happen? This is what my body is made to do, even if he's bigger than you or bigger than average, if he gets the right angle and adds some pressure, he'll go inside of me. If he goes inside, he'll want to move in and out and it will feel really good, then he'll push all the way in and ejaculate semen. If he's not wearing a condom to keep the semen from going inside of me, I could get pregnant with his baby. And now you know the secret to how babies are made."

"Thanks for the lesson" I said sarcastically "I'm so glad that I finally understand how this sex thing works."

As I finished the sentence I grabbed the base of the huge head and slowly pushed our new friend/toy harder into her and flattened the growing, giant head against her opening while simultaneously reaching down and rubbing her clit. She inhaled deeply and dropped her head while arching her back. As I looked down at her movement, I felt her lips slowly start to glide around the thinly stretched latex on the head.

"So, like this?" I said.

"Stop it. For real, I don't want it inside of me." she said, but this time with a little more leniency in her voice.

I wasn't worried at all about that. She is a small woman, and this thing rubbing her was massive and just didn't seem like it could ever get into her. It felt more like I was playing with her with a big dildo than a real person. It was just a toy that moved that I was using to tease her with. Feeling so safe about it, I just kept on pressing it onto her and playing a game trying to get her more and more turned on. He would push in and sink the top of his head in a little bit, then she would tense up, squeezing him out and move away or change the angle and he would slide down to her clit. This happened over and over when she started moaning more and I could tell that it was working and driving her crazy.

Even though I still wasn't completely hard in Jenn's mouth. The situation, her moaning, and getting her so wild was starting to have a real effect on me, and I could feel the start of that tingling in my balls. I knew that after a couple more minutes there was a good chance I might cum again, even if I wasn't completely hard yet. At the same time, she was starting to moan faster, and I could see her legs squeezing together and her back muscles starting to tense up a little bit.

I was getting pretty tired of bending over to keep a hand on him and my back was starting to hurt. So even though she had warned me, I placed him back at her entrance thinking he would slide back down again to her clit harmlessly and leaned up taking my hands off of the stranger's cock for just a minute to focus on what Jenn was doing to me. I just told her "I need to stand up for a second babe, just squeeze your legs together to keep him hard and hold him in place."

She started to squeeze her legs more when I noticed her legs tense which made her back arch a bit more, which I knew would just put him in a more wedged in position at her entrance.

She pulled off my hardening cock and said "God! I need to get fucked so badly right now. His head is hitting me right at my entrance. He's sliding that head in and out in little strokes instead of sliding down to my clit! He is so big, he's hitting the bottom of my clit every time he moves in though. What he's doing feels SOOO good, but I can't let him inside of me. Please hurry up, I need it SO badly and will probably be ready to cum in just a minute!"

"I'm almost hard enough now babe" I said, "just a few more minutes and I'll be ready."

"Could you just do me now?" she asked. "I really need it bad!"

I thought to myself, that as soon as I went inside of her I might just cum immediately at this point, and I definitely wanted to make sure she got hers or she was going to be upset. I thought to myself that I should see if he could get her right to the very edge then I'd finish her off. So I asked "Do you really think you can cum with him rubbing you like that?"

"With his head hitting my entrance and the bottom of my clit, if I let him keep moving his head in and out instead of pulling away when he starts to slip in, I might. It's really big, so if he starts go in a little more, it will hit my clit perfectly. But even with the condom on, I don't want him getting inside of me. It's not safe." she said as she squeezed her legs together.

"Ok, well, I just need another minute, could you let him get you right to the edge, then I'll get you the rest of the way? I want to make sure you cum hard tonight. Maybe just stop pulling away for a second and see how it feels?" I told her as she squeezed her legs together a little harder.

She thought about it for a second and then stopped rocking away and put a hand on my thigh for balance before saying "Baby, I want you, not this thing, and this scares me. But if you want, I'll do it just for a minute. But really, just a minute." she trailed off and stopped rocking forward.

After about 10 seconds her eyes popped open and she exclaimed "OHH!" Then while looking up at me, her her eyelids fluttered and her eyes starting to roll back back.

"Are you alright?!" I asked.

"Oh God, I willllll.... Definitely cuuuummmm.... If we keep this uuuuuup! When I stopped moving, he started moving really fast and a little harder in small strokes. The pressure at my entrance and him hitting my cliiiiit so fast each tiiiiime... feeelsss... sooooo..... gooood!" she said as she trailed off but put her head down to start sucking me again. At the same time, I could tell that she was squeezing her legs even harder and arching even more while holding herself in place with her hand on my leg.

My brain was starting to get foggy, but I thought as I looked down at her amazing hips that they were starting to buck up and down. Her body does this unconsciously sometimes when I haven't entered her yet and she is trying to get me inside of her. She just writhes around, and her body lines up with my cock. She would never let him inside of her, so I wasn't really worried about that, but with her writhing like this, I started to wonder if she was losing control.

Just then, I felt her moan really loudly with my cock in her mouth. She came off of sucking me for just a second and said "oh baby, this is so baaaad! He is lined up right at my entrance and thrusting deeper trying to get in, and he is starting to a little. And he is SO big. Are yoooou okkkk with thissss? If you're alright, I... I think he's going to maaaake me cuummm in just a... minuuute. We can stop if you... waaaantttt. Fuck, he is so BIG!!!!"

Without thinking, I just said "I'm so close to being hard enough and I want you to cum right when I go inside of you, so it's fine. How long till you'll cum?"

"Oh God baby, I don't know. He is driving me CRAZYYYYY! I am so wet and this thing is starting to stretch me open more now, and my legs are starting to shake so I can't move away as easily when he pushes harder. Also, he must be sliding inside the rubber. It is so slick and hot, it feels like he's not wearing anything!" she said as I noticed she had stopped writhing as much and was trying to move herself away from the wall, but was tensing up the way she does when she is about to cum.

Suddenly, she stopped tensing for just a second and got a funny look in her eyes, then a second later tensed again with a sigh then a squeal "mmmmm... OHH!"

She stopped moving her head and took her hand off my cock and started reaching her hand back when I said "Please don't stop, I am almost there.... Can you pleeeease keep going for another second. I am so close and I'll take care of you in just a second!" I told her, starting to feel a tingling in my body.

Her hand floated in the air for a solid second as she said "Ok, but please hurry up!! He pulled back through the wall for a second and pushed back in. Now he's starting to slide in and out again. It feels really good, but like, hotter and maybe smoother? I just want to check the rubber... it's really important!!" she said with some desperation in her voice while starting to move her hand back up towards me.

She put her head back down and started bobbing up and down and using her free hand on me as well, to get me there as quickly as possible. So I let my hands fall to her head as she bobbed up and down faster and faster. I closed my eyes, getting ready to pull out her mouth, spin her around, and mount her even though I was still not quite there when she suddenly tensed up and started moaning heavily onto my cock.

With the new sensations, and this crazy experience, I knew I was going bust soon and by the look of her body movement and the sound of her moans, so was she. Right then she starting just sucking my head and stroking the rest of me really fast with her hands. After I was wet enough she popped her head up while stroking me closer and closer to a huge orgasm.

"Oh God!! His head feels really good!!!" she said with pure lust in her eyes. "He is pushing in a little moreee... my legs are shakinggg so hard and I can't controlll it!!"

"It's ok babe," I said, trying to time both of us cumming at the same time "let him get you right to the edge, then I turn you around and thrust inside of you and we'll cum at the same time. Let that big head slide in and out a little bit more if that's what you need to get you there, it's ok."

"Condom..." she replied while starting to sink back a little more..

"It's ok to let yourself go for a few seconds" I told her. "I know you need to cum badly tonight!"

"No... Oh! No... it's a... bad.... idea" she said. She had stopped moving away on his thrusts and was holding still and tensed up.

"It's just for a minute." I said looking down as her legs started to shake harder.

"Ok.. Just for a minute.... He's start to GO INSIDE OF ME, and I'm going to CUM like this! Are you sure this is ok?" she asked looking up at me.

"Please! I'm almost there! Let yourself get to the edge" I said, which may not have been the response she expected. But as I said it, I could tell she was letting go as she started to tense up again, and seemed to have stopped rocking herself away from the wall at all.

Her hand stopped moving on me as she encased my cock in her warm mouth, put her hands onto my thighs and squeezed hard. I unconsciously bucked my hips forward while putting my hands on her head and kept her on my cock to prolong the feeling. I felt her jerk her head up for a second which I was unknowingly holding down and she gave a grunt and squeal, then let it fall back down when I felt her tense up and give a huge moan. Her moan made me buck my hips again, but this time a little harder. Her moan went from a deep guttural moan to a squeal in just a couple seconds while she started bobbing her head less and moaning more. I also noticed that she had jerked a couple inches away from the wall, and kind of cramped up against me. As soon as she took her mouth off of me though, she started moving her hand up and down along with her now quick back and forth motion and squeezing me. I was about to explode.