Annie's First Love

One night we were in her bed and starting to make love. I had squirted lube all over her ass and vagina. She had her legs spread wide and I lay next to her fingering her ass with the pointer and middle finger of my right hand.

"Do you think I'm ready for that blue dildo, Annie," she asked. Hopeful, fearful, excited.

"Without being too crude Jenny, your ass opens big enough for that blue dildo in the course of its' usual business. The only thing that has to be ready is your mind," I said. "You tell me, Jenny. Are you ready?"

She looked into my eyes and in a careful and almost imploring way said, "Fuck me with it Annie."

Soon she was on her hands and knees and I was fingering her ass. I got the lube and pushed the opening right against her rosebud and squeezed. Some came out the sides but I knew plenty was now inside her ass.

I then took the dildo and put the head against her asshole.

"Are you ready? I'll stop as soon as you say if anything hurts," I promised.

She looked a little anxious but nodded her head.

"On the count of three I want you to push down like you are taking a shit," I told her. "OK?"

She nodded again.

"One... two...three," I counted.

When I hit three I saw her sphincter push out a little and I very slowly pushed the dildo into her ass.

I got it a couple of centimeters in and stopped to see if she was alright.

"Are you OK babe?" I asked.

"Yeah, yeah that went in fine -- it didn't hurt at all. Keep going Annie," she said.

I was glad we'd taken our time to get her to this point. I kept feeding it into her ass and checking she was ok. Eventually it was all the way in. Once she had it all the way up her she relaxed and I could see it had taken a load off her shoulders.

She now eased back into simply enjoying it. I didn't push it in and out -- I wanted her to get used to the feel of it.

I wanted to share it with her face to face so I guided her onto her side so I could lie next to her. She lay on her right side with her left leg in the air. I lay next to her on my left with my head against her breasts. She had her right arm cuddling my head to her chest and her right reached down to fondle my breasts.

I had my left arm under her body and held her to me and used my right to hold the base of the dildo as I slowly pumped it in and out of her ass. I didn't fuck her hard or fast but eventually we got up a rhythm and it was like anytime I'd fuck her with a dildo except perhaps a little slower and more gentle. And she had a flushed look on her face like she was barely able to accommodate it all.

We kept at this for a long time and it was eventually too much for both of us. It was time to come.

We changed positions so that she had her back to me. I masturbated myself with my left hand and kept fucking her ass from behind. She used her right hand to reach behind and squeeze the arm I was using to fuck her. With her left she masturbated herself.

We came together and a new phase in our love making began.

For about a week or two every time we had sex it included anal. Then we slipped into a rhythm where if we had quick sex it was usually just cunnilingus and or vaginal dildos. But whenever we had a long sex session it always included anal.

She got to love that dildo in her ass so much that it became clear that if I was going to get the ass fucking I craved we were going to need another one.

We had the two vibrators, two medium dildos, the whopper, the thin anal dildo, the butt plug and a mini vibe I used for my ass. We talked about going to a sex shop and buying some new toys.

"I want a strap on so I can fuck you with it," suggested Jenny.

"I want a strap on so you can fuck me with it," I agreed.

"We need another ass fucking dildo so we can both do it at once," she said.

"Yep. And we better get another whopper in case we both need the ultimate full-fill-ment," I replied.

"Ooh yeah," she began to fantasize. "Sixty nine. I'm fucking your pussy with the whopper and your ass with the little one. And you're doing the same to me."

It wasn't long before we were acting it out. In sixty nine position she was fingering my ass and vagina and licking my clit and I was doing the same.

Soon we had to go to the next stage and so we got out the toys. I took charge and put the whopper into her vagina and the thin ass fucking dildo in her bum.

She was lying on the bed and I got up to get some more toys for me she took over masturbating herself as she watched me get out one of the medium dildos.

I also grabbed the little ass vibe we had. I stood next to the bed and fucked myself standing there as I watched her fuck her ass and pussy.

"No fucking fair," I said looking at the pathetic little ass vibe.

She laughed in a sort of teasing 'I've got it and you can't have it' way.

"Fuck it. We're getting new ones and I'm shoving this up my ass," I said grabbing the remaining medium dildo.

I lay on the bed right next to her and lubed up my ass.

"I don't think it's gonna fit Annie," she warned.

"We'll see," I said somewhat smugly.

I did get it in my ass but it was a very, very tight fit.

Jenny became very excited at the idea and virtually stopped fucking herself to watch me.

I abandoned the dildo in my vagina and just concentrated on frigging my clit with one hand and slowly fucking my ass with the medium dildo. I was surprised at how wide Jenny's eyes were and how transfixed she was to see me with the bigger dildo in my ass.

"What does it feel like?" she asked in a voice very heavily laced with lust.

"Tight. And fucking good," I said. I was getting off as much on her excitement as the sensations in my stretched ass.

It wasn't long before I came like that with Jenny watching me intently and she came with me despite having got rid of both dildos and just gently teasing her clit.

We talked afterwards and it became clear that Jenny was very turned on by the idea of putting something bigger into her own ass.

"Annie, I want you to fuck my ass with bigger and bigger toys until you can fuck my ass with a whopper," she said as lustfully as I've ever heard her say anything.

I hope to soon write about our adventures buying toys and stretching our asses. This has taken me forever to write because it makes me so horny I get 'distracted'. Please let me know what you liked and didn't like about it. Every time my inbox has feedback in it I end up coming again, thinking of someone enjoying my story. So if you got off on it do me a favour and tell me so I can come thinking of you enjoying yourself.