Long Lonesome Highway Ch. 02

Then I relaxed again, and she continued to insert more of her finger. It felt like it took forever, but was really only a minute.

She slowly started to move her finger around inside me. Stretching me, and incredibly, making me feel good. I was surprised, it actually felt nice to have her finger in my butt. Then she started to insert a second finger, and things got tight and a bit painful again. I had to relax, I knew that, and I had to breath. I started to concentrate on relaxing and breathing.

While Jessica was stretching my butt, she was constantly rubbing up and down my back, massaging me, forcing me to relax. Once she had her second finger inside me she again started to rub her fingers around inside me to stretch me further. As I got used to the two fingers in my butt she introduced a third, and again worked on stretching me further. I couldn't help feeling good after the initial pain of each new finger. I'm sure I was starting to moan a little, and lift my butt to meet her fingers. "mmm, That's it baby, relax for me, let me in, so I can make you feel good." She crooned in my ear.

Once Jessica noticed I had totally relaxed and was actually enjoying having her fingers inside me, she leaned down and whispered in my ear. "Do you think you're ready Baby?"

"Mhmm, I think so." I said

"Give me your hand."

I held my hand out, and she squirted some lube into it. "Cover my cock with it, make me nice and hard for you."

I started to wank her beautiful cock with the lube. Once she had reached full hardness I couldn't help again marveling at the size of it. Her cock was at least nine inches long, and at least another half an inch wider than mine. "Oh my God, Jessica. You're going to rip me in half with this." I said

"I won't rip you in half, but you will feel different for a couple of days, That I can assure you." She said, "But you will need to relax, or I will hurt you. The more you relax, the easier it will be."

I lay back down on the bed, face down. "No, Not like that Baby, You will find it easier on your hands and knees this first time."

I got up on my hands and knees. Jessica moved behind me. She was rubbing my back with both hands. Gently stroking her hands up and down to relax me. I felt her cock touch my butt crack. Oh my God, was I really going to do this? I moved back a fraction just to feel her cock more firmly against me. "That's it Baby," She crooned, "Want me. If you want me that will make it so much better for you. If you want me inside you, your body will open more willingly to take me in."

I did want her. I pressed back more. I felt her cock start to press against my puckered ring. I felt her slowly start to push herself against me. I felt the pain start, but I held myself back against her. "I want you, I want you, Please fuck me." I was a bit surprised to hear those words coming from my mouth.

I held myself back against her as she pressed herself forward. The pressure was getting more and more intense, and so was the pain. Then suddenly I felt the head of her cock pop inside me, stretching my sphincter like it had never been stretched before.

I cried out with the pain of it.

Jessica massaged my back gently, "Relax, Baby, Just relax, I'm not going to move now until you are relaxed and ready."

We just stayed like that, motionless, apart from her hands massaging my back. Slowly though, I noticed the pain recede. I still felt massively stretched, but it didn't hurt so bad any more. "See, it is starting to hurt less, isn't it?" she asked "Relax, and want me, it will hurt less and less the more you want me to fuck you."

I couldn't help it, "I do want you to fuck me, Oh God, I do want to feel you deep inside me, I want you to fill me with your beautiful cock."

I gently pressed back against her, and she gently pressed forward, sliding a couple more inches into my butt. Again I flinched from the pain, and again she stopped pushing and just rubbed my back.

Once I relaxed, Jessica pressed forward again and slid another couple of inches into me.

I guess most of the pain receptors are near the entrance of my anus because it was hurting a lot less now when she pressed more into me. She was still going in slowly and gently though, and she never stopped massaging my back, and whispering reassurances. "I can hear you starting to moan, it is starting to feel good isn't it?" She asked me.

Incredibly, it was. It felt so good to have my butt feeling so full of Jessica's cock. To feel all the nerve endings in my anus getting stimulated by the feel of her cock rubbing against them.

Jessica moved into me again, and this time I felt her hips against my butt cheeks. "My God, Are you all the way inside me?" I asked incredulously.

"I am now, you've done incredibly well. You feel so deliciously tight." She said, "I'm having to work real hard not to cum instantly."

"It feel so good to have you so deep inside me. I feel so full, and even my cock can feel the pressure behind it."

I reached down to grab my cock. "No, don't touch it." Jessica told me. "I want you to make it last. I want you to feel it build, until you can't contain it any more. Trust me, it will be worth it."

Slowly, gently Jessica started to withdraw from my butt until only her big cock head was left inside me. Then just as slowly, she started to push back into me again, until she was again pressing her hips against my butt cheeks. As she pushed in I moaned with a mix of pleasure and discomfort. It wasn't really pain any more, just intense pressure and discomfort. Again she withdrew slowly, and then filled me again just as slowly. Then she stopped, "Oh Don't move Baby, Please don't move." she begged.

I held perfectly still, I knew she was desperately trying not to cum.

Once she gained control of herself again she said, "I want you to slowly lower yourself down to the bed. Don't let me slip out of you."

"Now, I'm going to start making you feel really good." She told me.

With me laying face down on the bed with my legs spread. Jessica was able to slide her cock back and forth over my prostate. It felt incredible. It felt like I was having a gentle but continuous orgasm with every stroke of her cock in and out of me. I could feel my cock pulse with every stroke of her cock into my butt. I was moaning constantly, "Mmmmm, Oh yes, fuck me, you feel so good inside me. Mmmm."

"I told you I was going to make you feel good." she said as she kissed my neck and nibbled my ear.

I could feel her beautiful DD breasts pressed hard against my back.

I reached back behind me and wrapped my hand in her red wavy locks. "You did tell me that, and you are right. It feels so good."

I pulled her face down toward me and twisted my head back as far as it would go so I could kiss her mouth. "Kissing like this isn't easy Baby, wait till we finish." she said, as she kissed my shoulders and my neck, and again nibbled on my ear.

I was starting to go from moaning to groaning, I could feel myself cumming. "You're making me cum Honey, Cum with me."

She increased her strokes into me, filling me totally with each stroke. Faster and faster she thrust into me, until she could hold it no longer. "NNNNGGG, I'm cumming nnnnggg, nnnnggg, nnnggg," she groaned out aloud

She pumped herself deep into my body again and again, filling me with the cum that she had left after I made her cum earlier. Then she collapsed on top of me. "Oh my God, that was incredible. Are you OK Baby?" she asked me.

"Mhmm, but I think I'm going to be walking funny tomorrow."

We both burst out laughing. "I can guarantee that." she said.

We went to sleep like that, me on the bottom, and her on top, with her cock still buried deep inside me.

In the early morning, just before dawn, I felt her kiss the back of my neck and then withdraw her cock from my butt. Then she got up.

I was still more asleep than awake. She went to the shower, and I went back to sleep to the sound of running water.

I woke up again about an hour later. Jessica was gone. There was a note on the bedside cabinet. "Bruce, Baby, Thank you for a truly wonderful night. When you get to bring your truck down around Canberra call me. XXX Jessica."

The note had her phone number and a lipstick imprint of her lips next to her name.

I got up, and walked somewhat gingerly to the shower, I was definitely feeling sore and well used.

I got myself cleaned up and shaved.

When I walked back into the bedroom I looked at the bed we had slept in. We had made as much of a mess of that one as we had the first one. I chuckled and said to myself, "It was worth it."

I pulled a fifty out of my wallet and put it on the bedside cabinet for the cleaners, and I put Jessica's note into my wallet.

I walked out of the motel room and headed to my truck, very conscious of the funny way I was walking. I knew I'd need a couple of days to get over last night.

Once I had the truck warmed up, I again headed north, to deliver my load to Queensland.

I knew that as soon as I dropped off the load in Queensland, I was going to be looking for a load that would take me to Canberra.