Jess and Me Pt. 03

Jess started to lift her hips and moaned. She reached up with one hand and started to play with her nipples. I started to push harder with the dildo but with the lube making it all slippery, my hand kept slipping and I could not hold the dildo tight enough to get enough pressure to push it into her tight pussy. I was laying on my left side next to her. Being as I am much taller than her, I slid over closer and slid my knee under her right leg. This allowed me to move my knee up to the base of the Dildo and help hold it in position. Now don't worry, this is not going to get obnoxious like I had to use a forklift to get it in there, but what this positioning of my knee did do is allow me to keep some constant mild pressure on it without my hand slipping.

Using my knee, I lightly put pressure on the bottom of the dildo, and I slid my hand up on the slippery shaft to guide it into her pussy. This leverage allowed me to very slowly apply steady pressure to ease the big head into her tight opening. I continued to talk to her to keep her mind focused on the fantasy.

"He is so hard now; he wants to be in you, and he starts to push his fat cock harder into you. He knows it's going to hurt you at first, but he can't wait anymore. He needs to feel your pussy around his cock. He starts to push harder as your pussy resists to let him in." I was now pushing on the dildo with more constant pressure. I could feel her pussy starting to let it in. I used my hand that was around the shaft of the dildo to slide up to her pussy and run my fingers around her wet and slippery lips. I started to massage her pussy lips around the head of the dildo allowing her smaller lips to get well lubed and also making sure they were spread around the head and wound not impede the massive head from going in. Jess started to moan and started to arch her back a little to meet the pressure. I continued to rub her pussy with my fingers and continued the steady pressure with my knee. I could feel the dildo moving forward now and then almost exactly the way she had described it to me, there was a breakthrough pop feeling as the head got through her hole and into her pussy.

Jess let out a big gasp and grabbed my arm to stop me from pushing it in any farther, "Oh my God, that hurts. Fuck, it's too big."

"Shhh, just relax babe and allow your body to adjust. I won't move it. Just relax let your pussy adjust to the size. If it hurts too much Ill pull it out if you want me to."

She remained like that for about 20 seconds and then I could feel her start to loosen her grip on my arm. Using my knee, I was just keeping enough pressure on the dildo to hold it in place. I slowly started to run my fingers around her pussy lips and massage her clit. I could feel how tightly her pussy was stretched around the dildo. It was causing her clit to be fully exposed and pulled out from her hood.

"Baby, feel your pussy, feel your lips, your clit at how they are spread around his big shaft," she reached down and rubbed her fingers around the dildo. We both used our fingers to explore her pussy and the dildo. We did this together for a few minutes teasing her and enjoying the sensation. This allowed her to fully relax, and she pulled her legs up more allowing her hips and pussy to open up. When she did this, I could feel the dildo slide a little bit more into her from the pressure I still had on it holding it in place with my knee.

"He can feel how tight your pussy is and that makes his cock even harder knowing he is stretching your little pussy. He slowly starts to slide his cock into you just a little at a time, allowing you to adjust to his size. He can tell your pussy is not used to something this big and it excites him knowing this." I slowly pushed it in about another inch and then I let the pressure off with my knee. I took the dildo with my hand, and I slowly backed it out to the point to where just the head was still in her. Then I pushed some more pushing it in 2 or so inches now.

"He slowly starts to work his big cock into your pussy as you loosen up. He can feel you stretching around him as he starts to slide into you. Your little inner lips are stretched to the max and you can start to feel them being pulled in with the shaft as he starts to slide into you."

"Oh God, it's so big. Fuck it's so big." She said as she started to slowly grind her hips to meet the small in and out movements I was doing. I pulled it out to just the head again and this time I pushed it harder to the point it slid in a good 4-5 inches. She let out a big gasp, arched her back and grabbed my arm again really tight. The room was dark, but I could see well enough that I could see she also grabbed her left breast with her left hand and squeezed it tightly at the same time. I took this as a green light to keep going.

"He wants your pussy now. He does not care if it hurts or what you want. Right now, he just wants your pussy around his cock, and he wants to fuck you." As I said this, I pulled it out and pushed again fucking her deeper with it. I had my fist around the base of the dildo and due to its length was still able to push it in her a good 6 inches. Slowly I started to pick up the pace.

Jess started to moan; it was a low moan that was different then what I have heard from her before. She was grabbing my forearm tightly as I fucked her pussy with the dildo but at the same time, she was raising her hips to meet each thrust. Her moaning continued so I kept going.

"He wants to own your pussy. He is going to fuck you deeper than you have ever been fucked," I grabbed the dildo by the bottom and pushed it into her as far as it would go. I pulled it back out and pushed again pushing it into her until it could not go in anymore. It was long enough that even when it bottomed out, there were still a couple inches of the dildo hanging out of her pussy.

Jess started to moan louder and was arching her back more, I continued the fantasy, "His big head is so deep in your pussy, he wants to shoot his load way up in your pussy. Way in there where only a big fat cock can reach," I started to fuck her hard now. She was moaning then started saying "fuck, yes, oh my God, don't stop, keep fucking me."

"His big balls are tightening up. Your tight pussy is too much for him. He can't last much longer, and he starts to fuck you faster and deeper," I started to really fuck her with the dildo now. Her orgasm was building, and I knew it was going to be any second now.

Jess kept saying, "Oh God, fuck, oh God, yes, holy shit," she was grabbing my arm that I was using to fuck her pussy with both hands now. Her right hand was grabbing my forearm. She was not really helping me fuck her with the dildo but was holding it tightly as though she was grabbing the guy that was fucking her. With her left hand she reached up and was grabbing me around my right shoulder now. She had started to dig her nails into me (which was starting to hurt). She was arching her back and said, "Oh God, fuck. Yes. Oh my God, yes."

Her body started to shutter almost starting at her shoulders and working its way down her body. She arched up and screamed, "I'm cumming, oh fuck I'm cumming." Her whole body was shuttering now, and she was moaning a low guttural moan that was different from any previous orgasms she had had with me. "Oh God, don't stop, don't stop. Deeper, fuck me deeper, harder, yes, FUCK!!!" she had her ass lifted off the bed now holding that arch while I was fucking her. I was thrusting in and out of her deeper and harder. I had never seen her have an orgasm like this one. "Oh my God, I am cumming again, don't stop, keep fucking me, harder, fuck, yes, oh my God," she continued to arch her back up and I continued to thrust in her. Fucking her with the big dildo.

Her moaning slowed down and she let her ass come back down to the bed. She then said, "slower, oh God, shit. Stop, just hold it right there," she reached down with both hands and stopped my hand from moving with the dildo but also holding the shaft of the dildo keeping it deep in her pussy. "Yes, right there, fuck. Don't move, don't move, fuck its big." As she lay there like this holding the dildo in her, her body would shutter about every 5-10 seconds. Later, she would tell me that they were small aftershocks of her orgasms. "Mmm, ok slowly pull it out, don't go fast, ouch, I'm so sore."

I slowly pulled the dildo out until the head was the only thing left. There was a noticeable difference in resistance when I got to the ridge of the big head. I griped the dildo tightly and give it a slow and steady pull until it finally came out with that pop sensation again. Jess let out a little gasp and whimper as it finally came out.

I leaned over and kissed her. I tried to touch her pussy with my fingers, but she stopped me and told me it was too sensitive. I laid next to her on my back for a few minutes and then she rolled over to me and started to lightly stroke my dick with her fingers.

I broke the silence, "I would definitely say that was a good purchase."

"Mmm. At first, I really thought it was too much and was not going to work. My pussy is so sore right now," she said.

"I bet you forgot about that didn't you? The soreness after a big cock was in there," I asked. My dick fully hard now under her light stroking.

"Yeah. It burns right now right at the top of my opening just under my clit. I remember that now. How it used to burn like the skin was stretched too far or something. It feels like that again right now,"

"Did your pussy always get sore after getting fucked by the BC?" I asked.

"It was always a little sore after. I always had that burning sensation after too. I had forgotten about that. The first time I had sex with BC my pussy was so swollen and sore. I just remember driving home after the first night we had sex and it was so sore that even sitting in the care was uncomfortable," she told me and started to stroke my dick with her whole hand now.

"Will you stroke me like I like?" I asked.

"Of course," she answered.

I reached into the nightstand and got out some Vaseline. With her lying on her back I knelt over her with a knee on their side of her. She took some Vaseline on her hand and started to stroke my dick with her right and then reached under me to play with my balls with her other hand. I would then lean forward on my elbows, so my head was close to hers, but she had room to reach under me and stroke my dick and balls.

I loved this position. My balls are small and always tight, so this makes them hang down some and makes them more accessible then when I am laying on my back. It definitely feels better to have them rubbed like this and it is one of my favorite things. I also enjoyed being in this position when we talked about big cocks. Her stroking my dick and telling me how she likes cocks that are much bigger or describing an ex that was bigger was such a huge turn on.

"That feels really good. I got so horny using that dildo on you. That was a very intense orgasm," I told her.

"I know. It was kind of embarrassing. It was just so powerful I couldn't really control it at all," she said.

"Nothing to be embarrassed about. I just think you really needed that," I said.

"The orgasm or the dildo?" she asked.

"Having a big cock in you. It's been a long time since you have had a big cock and I think you were craving it more then you let on."

"I don't know if crave is the right word but its hard not to think about it since we talk about it so much. I think it was just a build up from all the talking and the fantasies," she said.

"Tell me how it felt," I asked. "Describe it to me."

"It felt really big. I didn't think it was going to go in at first. Remember how I told you that with BC there would be this pressure when he went to put it in? That was the first thing I thought of. You were pushing and there was a lot of pressure before it finally went in."

"You don't get that pressure when I go in you do you?"

"No not like that."

"I kind of just slide in, don't I?"

"Yes, it's a good fit. Your head isn't much wider than your shaft, so I think that is part of it," while she said that she was feeling around the head of my dick almost like she was analyzing what she was saying. I loved when she does that and I loved the comparison.

"The dildo has a big head on it. Was that how BC was?"

"Yes, he had a very big head."

"Would you say my head is proportionate to my size or that I have a small head in general?" I asked craving more comparison.

"BC had a big head, and you could feel the ridge around the edge that made it wider than his shaft. The edge of your head is not much wider than you dick which is why I think it makes it feel smaller," she said. Again, feeling around the head of my dick while she was talking. I was enjoying this immensely and I was so horny I could feel it in my balls.

"Did you feel really full when it finally went in?" I asked.

"Yes, and very stretched. I can still feel the burn a little from the stretch. I can also feel my pussy pulse with every heartbeat right now. It like a little throbbing feeling. I felt really full and stretched wide. I think as far as the thickness, it is the head that really stood out. I could feel the ridge of the head as you moved it in an out of me," she said. She was again playing with the head of my dick as she talked.

"Do you feel my head when I am fucking you?"

"Sometimes at first I do, but then I get wet and exited and I don't feel it anymore."

"Do you like that? The head being bigger than the shaft?"

"Yes. When it goes all the way out and then back in, I can feel the head kind of pop as it goes in and out. It hurts a little but in a good way."

"I think you really needed that big cock in you. I think you were really craving that."

"Maybe a little. You talking to me while using it on me was really hot. That made it a lot better," she said.

"I wish you would just admit it that you like getting fucked by a big cock. We both know it. I just want to hear you say it."

"Yes of course I do. We talk about it all the time."

"Ok here is what I really think, and I want you to be completely honest, I think that it's been a long time since you have had a big cock and you forgot how much you liked it,"

It took her a few seconds before she answered but she finally said, "Yes, I guess so."

"Admit it, you miss getting fucked by a big cock, don't you?"

"Sometimes," hearing her admit that made my dick harder. This type of talk was pushing me over the edge.

"Tell me the truth, do you sometimes wish I had a big cock?"

"Sometimes," she said kind of quietly.

"Feel my dick, lightly stroke your fingertips along it. I am so excited right now."

"Its really hard and your balls are so tight," she asked.

"I know you like big cocks and I love that. I knew you wanted to feel a big cock again, I could tell by the way you have been talking and reacting lately. I want you to know that it is ok that you want or need a bigger cock then mine. I don't want you to be afraid of how you feel. It turns me on."

"Ok, but I love sex with you. I don't want you to think I don't."

"I know you do. This is all part of our sexuality together. From fucking, to playing with toys, to talking about our fantasies. It is all part of our sex life. My lack of size or your craving of big cocks is not the only thing that we have as a couple. We are so much more than that. So don't be afraid that you want a bigger cock then I have. Don't be shy about it. I am ok with it, and I now know that you sometimes wish I had a big cock to fuck you with. We can enjoy that and use the big dildo and explore that desire together."

"Ok. This is all so new to me. Will you fuck me now? I really want to feel you and be with you."

I moved down from her and slid my dick into her pussy. She was so lose compared to how she usually is. It felt almost velvety compared to the usual tight grip she had on me.

"Can you feel me?" I asked.

"Yes. Do I feel different?"

"Yes, looser but it feels almost velvety and soft. I can tell something big was just in there."

"Do you like that? Does it turn you on?" she asked.

"It turns me on that I know this is what your pussy feels like after a big cock was in it. I like how tight you are but now I know it was just stretched out by a big cock and that turns me on too."

"You are so different then anyone I have ever met. I have never talked liked this and never had such an open conversation about these things. I hope this does not change," she said. She sounded so sincere I just kissed her.

"I don't want it to change either babe. I have never been this honest with anyone either and I love that we can explore this openly together. I promise I won't turn on you one day and hurt you with our secrets."

"That really scares me, but I do believe you. Oh, you feel so good right now. Kiss me."

I kissed her and we fucked slowly and then I started to pick up pace. She reached under and she started to play with my balls which I love. We continued to kiss and then I broke the kiss and I just looked down at her while I fucked her. It was dark but I could make out her face and she could make out mine. We just looked at each other while we fucked getting faster, then slow, then faster, keeping me on edge until I could hold it no longer and I leaned in and kissed her while I came deep in her pussy.

After we just laid there for a while. I kissed her and lightly played with her nipples some as we just relaxed in the aftermath of sex. Then I noticed that she had started crying quietly.

"Babe what is wrong? Are you ok?" I was seriously concerned and completely caught off guard. Fuck, what did I do? Did I push her too far? Oh man hurting her feelings was the last thing I ever wanted to do. "Sweetheart I am so sorry, what is wrong? Please tell me!"

She quietly cried a little more as I stroked her hair and I then I pulled her on top of me and just held her tight. She laid on my chest and I just held her, lightly rubbing her back with my fingertips. We stayed like that for a few minutes, and she finally broke the silence.

"I'm sorry. I didn't mean to cry," she said.

"I am sorry babe if I did something or if you did not like what we did. Last thing I want is to hurt you."

"I know. That is just it. I don't think I have ever been this open with anyone it scares me and then I just got overwhelmed and that scared me more."

"What we were we doing or talking about was overwhelming or just the moment in general? Help me understand," I said completely sincere. This totally caught me off guard and I felt like shit. I thought we were just having fun and the last thing I wanted was to hurt her feelings or drive a wedge between us because I was chasing crazy fetishes and fantasies.

"No nothing like that. I love what we were doing. I love that about you, how open minded you are and how safe you make me feel," she paused there, and I started to say something when she interrupted me, "Don't say anything, you don't need to do anything, but I just want to be honest with you right now and it really scares me. Just don't say anything ok?"

"Ok," I said, nervously.

"Promise me you won't say anything ok. That's what scary to me right now is what you might say. No matter what promise me you won't say anything. Just listen."

"I promise. I will just listen. I won't say anything," I meant what I said but I was also concerned. What had happened to her that she was going to tell me?

There was a quite pause and about 5 seconds of silence before she told me what she was thinking. During this time, I thought the worse. My thoughts were random and fast. They ranged from, "oh man did I push this too far?" to angry thoughts about "what did somebody do to her that hurt her?" and then I had sudden flashes of rage thinking, "I am going to fuck this dude up that hurt her." I had all these random thoughts in under 5 seconds until she finally spoke.