For the first few minutes I slowly worked in and out until I could finally get my full length inside. For this entire time Julie had her head buried in a cushion, and she was whimpering softly. I suggested we should stop, but she told me to keep going. Apparently it would get better. I kept adding lube to the equation, and this did seem to help as eventually fucking Julie’s ass stopped feeling like somebody was trying to skin my cock using just pressure. If there is no slip it is amazing how far the skin on a penis will stretch.
“Damn it Darren,” Julie moaned into the cushion, “what are using back there? That feels twice as big as it was yesterday.”
“It’s the same,” I assured her as I kept working back and forth.
After a while I was just fucking her gently and Julie finally lifted her head and looked at me. I could see she had been crying.
“It is getting a bit better,” she said, half hopefully, and I nodded.
“Is it good for you?” she asked.
“It is amazing,” I told her, and she nodded.
“Speed it up a bit Darren,” she managed to say through partially gritted teeth, “I want to feel you cum inside my ass.” I nodded.
I’d like to tell you that Julie got right into it and came four times from her first ass fuck, but that isn’t what really happened. I did get up a good pace, and she did start moving with me, and she definitely did stop crying, but that was about all there was to it. I was sweating profusely as I fucked that tight little ass and I could feel my orgasm approaching.
“Ready?” I gasped.
“And waiting,” she said sounding rather keen for it all to be over.
The last thing a man usually does when he is about to cum is bury his cock as deep as possible inside whatever it is that he has that appendage in. You can call it biology, you can call it instinct, or in Julie’s place you can call it torture. She shrieked as I pushed my cock full length into her and then sighed with relief as she felt it pulsing as it unleashed a torrent of cum. I eventually fell forward, exhausted, but managed to use my elbows to keep most of my weight off her.
“Are you OK?” I finally asked, and she nodded.
“I think I’m going to need more practice with that,” she said, and I was relieved that wasn’t saying something like ‘never again’. At least I hadn’t made her initiation that bad.
We waited until my cock shrank down, but she still groaned when I pulled it out.
“Pool?” I asked and she shook her head.
“Today you come in and have a shower,” she told me, and I could understand why. No Matter how clean she had made her ass there would always be some concern about hygiene.
“When can you change the last screens?” Julie asked, reminding me of the reason for all of this.
“Now,” I told her, and I clicked my fingers theatrically. “Done,” I said smugly and she stared carefully at the final wall.
“You already…”
“I told you I was ready to let you off that one,” I said seriously.
“Are you glad we did it?” she asked and I gave her a huge satisfied grin. She nodded and said “Me too.”
“What now?” I asked her as we both seemed to have recovered.
“What do you suggest?” she countered.
“If you can put up with my work clothes when you are dressed up so well we could go out for dinner,” I suggested, and then I realised what I had said.
“Are you asking me out on a date?” Julie asked, looking at me seriously.
“It doesn’t have to be,” I said back peddling madly, “I know I’m way to old and ugly for a beautiful woman like you.”
“Really?” she asked.
“Look it was the bet that led is to do this, so I won’t over estimate my place in your life but I…”
“Ssssh Darren,” Julie said, placing a finger on my lips. “None of this was actually about the bet at all.”
“It wasn’t?” I was confused.
“I’ve really got enough put aside to do the whole job over again,” she said, and she giggled.
“Really?” My head was spinning.
“What this was all about was me trying to finally find a way to show you how attracted to you I am.”
“You are?” This was totally out of control.
“I want us to go inside and have a shower together. I want us to go out on a romantic date together. I then want to come back here and have you take me to bed. If we are both up to it I want you to fuck me to sleep and then fuck me awake tomorrow.” I was staring at Julie, my mouth wide open in astonishment.
“I love you Darren,” she said, “I love who you are and I love what you do to me. I don’t care about age and I think you are the most handsome man I have ever met. I want to learn about things from you. I want to learn about sex, I want to learn about music, I want to learn about movies, I want to learn about landscaping. I want it all. So,” she demanded, looking straight at me, “what do you say?”
“I say yes Julie,” I said sincerely, “and I think I am the luckiest man alive. I love you too.”
We kissed then, and this time I was able to put all my passion into it. This wasn’t a onetime thing anymore, this was my new life. Julie finally turned and gingerly walked toward her clothes.
“Let me start by telling you,” I said grinning, “about Roy Rodgers.”