Annie's First Love

In some ways this was especially true in regard to Jenny because I was so desperate to keep what we had and not jeopardise our beautiful relationship. So I just watched and tried to contain my excitement at seeing anal sex on the TV.

"Oh Jesus, that's got to hurt," said Jenny.

I sort of copped out with a quiet, "Mmm" of ascension.

"Carl put his finger in my ass once which was quite nice actually," Jenny confessed to my astonished delight. But she continued, "But when he tried to put his cock in I mean there was no fucking way it was going in without a whole lot of pain. I told him 'No way!'"

I waited a second before responding to think about what to say.

"I'm sure with a bit of patience and a lot of lube it would be alright," I ventured, with just a tiny hint of authority on the matter.

"I suppose," said Jenny, only half convinced.

A second later the penny dropped for her. She sat up and looked at me and somewhat urgently demanded, "Do you shove those dildos up your ass Annie?"

She looked me in the eye for an answer.

She had stopped fondling my nipples even though her hand was still on my breasts. I said nothing for a moment and kept caressing her nipple. I snuggled into her to encourage her to keep pleasuring me. She took my lead and started to fondle me again.

"Don't be fucking ridiculous Jenny," I said firmly. "If you stick something up your ass and then up your vagina you can get all kinds of dodgy bacteria in there. It can make you sick. There's no way I'd put one of those up my ass."

Thus reassured she looked at me a little suspiciously and put her head back on my shoulder to resume watching the DVD.

I decided to just get it out in the open. I waited a few moments more before saying in a self righteous tone, "Fuck Jenny. What do you think I am?"

And then I said, with a tone of vindicating explanation, "I've got a completely different box of toys for putting up my ass."

She stopped fondling me. She didn't move except to turn her head and look at my face.

"You're serious aren't you?" she asked.

"As I always am my precious little doubter," I answered.

She jumped up and stood before me and had a look of shock on her face and I had a terrible moment of horrified worry before she spoke.

"Get them," she said pointing to my room. "Now!"

I ran to my room thrilled at what had happened. I got my small butt plug, my small vibrator and my thin dildo and the box with the other toys and lube and went back into the lounge.

"You are a never ending surprise Annie," said Jenny as I came back in. She was now masturbating herself with her hand in her panties and looked very aroused.

"Gimme a look," she said still playing with herself.

I showed her the anal toys and as I turned and bent to put them on the coffee table in front of us she pulled my panties down to my ankles. All of a sudden she was standing behind me and a little to my right with her left hand squeezing and rubbing my ass cheeks. I opened my legs as she reached right under and pushed her middle finger in my now very wet vagina and casually masturbated me.

She then leant down and with her right hand picked up the butt plug which had a wire attached with a four speed control.

"How does this work?" she asked.

I bent to take hold of the control as she stood up straight with the butt plug in her hand. I deliberately bent at my waist more than I'd strictly speaking have had to and Jenny used the opportunity to switch from fingering my vagina to ever so tentatively touching my rosebud.

I cranked the butt plug vibration up to full -- it was one with a real kick -- and said, "You put it in your ass and that bit at the bottom stops you losing it up there."

"Fuck me, it packs a punch," she said referring to the vibration.

"Yeah, it's a fucking ripper," I said.

"Doesn't it hurt?" she asked looking at its width. It was no wider than two of my fingers but I guess it looked big to her thinking about putting it in an asshole.

"You just have to take your time," I explained. "If I really want to fuck my ass hard and fast I usually put that in for a while to loosen it up. After it's been in for about ten minutes it gets my ass so ready that with lots of lube -- you know too much is never enough -- I can fuck my ass as hard and fast as that porn chick. Not with anything big like the cock she fucks but with that thin blue dildo," I said referring to my slim anal dildo.

"Fuck me, Annie, I can't tell you how it turns me on to hear you talk about that," she said, and as she did she pushed her finger into my ass. It had been weeks since I'd had anything in my ass. All of the sex I'd been having was with Jenny and obviously not including anal.

She was being so gentle as she pushed her finger in as far as she could and the feel of something in my ass again was fantastically sexually thrilling in a physical sense. But much, much more than that was the excitement at being able to share anal sex with Jenny. It was unimaginably liberating for me to hear that she was turned on by the idea. I felt like I was going to explode with the emotional joy of at last revealing this deepest secret of mine in such a lovingly sexual context.

On top of all that because of the position I was in with Jenny behind me slightly to my side, with her finger in my ass and the coffee table hemming me in from the front I felt so vulnerable. Not that I wanted her to stop but she was in the position of control especially once she reached around with the vibrating butt plug in her right hand and put it against my clit. That had the obvious effect of sending my clit wild but also trapped my right arm against my body. My left wasn't able to reach her and besides I was still clutching the vibe control.

I was surprised how exciting it was to have that feeling of vulnerability and someone else able to do as they pleased with my asshole. I leaned into her to let her know how good I felt about it all and pushed my ass back with every little finger fuck she gently gave my bum.

"Can I put this in your ass, Annie?" she asked in the quietest, kindest voice.

"Oh, please Jenny, please put it in my ass. I would really love that so, so much," I said and I was genuinely shocked at how pleadingly desperate I had sounded. I was actually begging her to do it to me. I never thought I would feel such an acute need for someone else to do something for me sexually.

Jenny was being incredibly kind and gentle in the way she touched me but I had made myself her absolute prisoner by my overwhelming, overpowering need for her to anally stimulate me.

I half fell, half crawled onto the coffee table so I could put my ass high into the air and expose it for her. In the process in knocked over a pile of magazines and a glass of water and I could not have cared less. I just shoved things out of my way so I could get my legs wide open. As I did this I grabbed the lube and passed it back to Jenny. Then with my face and shoulders against the cold surface of the table I used both hands to spread open my ass cheeks.

"Please, please, Jenny," I begged. My voice was desperate, thin, feeble, needy.

There was a moment when I lost all physical contact with Jenny as she got the lube and plug ready. Then I felt the coldness of the lube in my ass crack as Jenny squeezed it out.

And then, exquisitely, I felt the tip of the butt plug, still vibrating on full, up against my asshole. She pushed it in just a little and said, "Is that OK, babe?"

"Oh, yeah...more...please, please" I responded.

Jenny slowly eased it all the way into my ass and when it got past the widest point my ass muscles clamped on it and it popped in. It always made me feel so full at first when the plug went it and was very gratifying.

Almost as soon as it was in I felt a sense of control over myself again. Now I felt like it was time for some serious fucking. Now my need was to get my hands on Jenny.

I got off the coffee table and turned to face Jenny. I grabbed her and kissed her passionately. I pushed myself closer to her and grabbed her ass cheeks as our tongues met and danced. I was ravenous for her and I put my hands into her panties and pulled her ass cheeks apart and put one finger against her anal opening.

Now it was her turn to feel vulnerable and I sensed her timidity at my gentle probing. This calmed down my urgency because I cared for her so much and I wanted to make her feel safe and loved.

I gently but firmly pushed her back onto the couch and got on my knees in front of her. She quickly took off her knickers and grabbed her own legs to hold them right against her chest so her vagina and asshole were very exposed to me. It was a very definite invitation to play with her bum.

"Be careful Annie, I'm not used to it," she said with a mix of excitement and fear.

I quickly got some lube onto my hand and started to rub her rosebud. She had a beautiful look of lust and trepidation on her face.

I started to work my tongue against her clit as I ever so gently eased my little finger in her ass to the first knuckle.

"Oh, fuck that's nice, Annie," she said.

I remembered when I had started fingering my own ass and so I took my finger out and gently put it back in again. I kept this up as I licked her, my little finger going in just up to the first knuckle and out again, over and over.

I stopped licking her to say, "I'm going to put my finger all the way in now Jenny."

"Yes. Do it," she said.

I could feel the butt plug vibrating in my ass, making me feel so delightfully full. It was beautiful to think of her sharing my anal pleasure at the same time.

I used my middle finger and slowly pushed it all the way in, licking her clit and labia the whole time. She started humping gently so I used the thumb of my other hand to fondle her clit as I pulled my head back and watched myself slowly fuck her ass with my finger as she fucked back with tiny thrusts of her hips.

"Oh fuck, Annie, that is just wicked," she said enraptured.

She was playing with her own breasts and nipples and was a beautiful sight to behold as I finger fucked her ass. I was clamping my own ass on and off the vibrating butt plug as I swayed my hips back of forth in rhythm with her mini humps so I could feel the fullness of it in my ass.

I've never have a full blown orgasm from ass play alone but with both my nipples and or my ass I can achieve mini orgasms. I'm not sure if 'mini orgasms' is the right term -- I usually think of them as 'nipple orgasms' or 'ass orgasms'. They are longer lasting than a full on orgasm and can go on for up to a few minutes and the intensity of sexual pleasure is very near a complete orgasm. Rather than finishing with a bang they just ease away and rather than feeling sexually spent afterwards I'm still horny as hell. Technically I suppose the main difference is that they don't include the involuntary spasmic pulsing of the vaginal muscles and sphincter that accompany a true orgasm but I do get the compulsive hip shudder more so than with actual orgasms.

I could feel the slow rise toward one of these 'ass orgasms' as I fingered Jenny's bum and massaged her clit. Watching her pleasure build I became feverishly excited at being able to give her so much joy from just a finger in her ass and a thumb gently massaging her clit. It gave me a great sense of power to do so much for her with so little. I felt as much like I was fucking her like crazy as I did when I hammered a dildo into her vagina at high speed.

On top of that was the eruption of years pent up sexual anxiety about anal sex. At last I was sharing anal sex with someone else. My thoughts and emotions were running rampant. Despite my wonderful relationship with Jenny I still couldn't stop feeling nervous and frightened about it.

It was my finger in her ass and it had been me that had whimperingly begged her to put the butt plug in mine. I knew I'd been the one pushing the anal angle and that made me anxious about it. So every indication she gave me that she was enjoying it too was an enormous relief to me emotionally. And every hint she was getting off on anal also made me intensely sexually aroused.

When I had showed her my sex toys a few weeks ago I knew I was exposing something of myself and taking a risk and that had been both frightening and exciting But fingering her ass with a butt plug in my own was ten times that on both fear and pleasure measures.

I had become used to the signs of Jenny's approaching orgasms and I was overjoyed to hear her breathing quicken and her back arch and her mouth open giving me all the tell tail signs. My 'ass orgasm' began to peak and I quickly replaced my thumb with my tongue on her clit.

I was so desperate for her to enjoy it that I licked her as hard and fast as I could and by the time she came my tongue was aching and my hips were shuddering and my ass muscles were clamping hard -- super hard -- on the butt plug.

Once she came I stopped licking her clit and slid my finger out of her ass and looked into her face. Even though she had very obviously enjoyed it I still felt very anxious that she would be OK about it post orgasm.

We had got to the stage in our love making where we usually managed to synchronise our orgasms and if one of us left the other behind we had this unspoken rule that it was her job to then give all her attention to the laggard.

Despite this I sort of thought there'd be some post anal debrief while Jenny came to terms with what had happened.

It was not so.

In a moment she was off the couch and kissing me as we stood on our knees. As we kissed she reached behind me to grab the plug in my ass and gently wriggled it about. Then she bent me over the couch putting exposing my ass to her. She pushed the coffee table out of the way and used one hand to rub my lower back as she gently pushed and pulled at the butt plug.

With my right hand I gripped the armrest and squeezed hard, partly as a response to my excitement and partly so Jenny could see my excitement. With my left I reached under and fondled my labia and clit which was very sensitive after my 'ass orgasm'.

Jenny pulled at the butt plug and the widest point popped out and then she pushed it back in past the wide point again.

I was too emotional and excited to say anything intelligible but I managed a few, ohs and pleases and yeses.

Then for a moment Jenny wasn't touching me at all and I could hear her grabbing something. In a flash I felt something probe at my vaginal opening. I was in a state of utter lust and reflexitively pushed against it. It was already in me before I realised it was the whopper -- our biggest (but not gigantic) dildo.

Neither of us had ever put that into the other without asking first -- it just wasn't the sort of dildo that went in easily enough to be done without warning.

I don't know if Jenny thought about it in this way but it was the best thing she could have done and not just because it felt so good. By having me bent over like that with her hand on my lower back holding me in place and shoving that big dildo into me I felt so vulnerable and that she was so much in charge.

I needed her in charge so that I could relax about anal sex. I didn't want the anal thing to be all my direction. I wanted -- well really more than that I needed -- her to be proactive about giving me anal pleasure. I needed her to be actively enjoying playing with my ass.

I felt so full and stretched and vulnerable as she fucked that big dildo into me -- especially with my ass filled by the butt plug at the same time.

She popped out the butt plug and held the big dildo all the way inside me and said, in her usual, casual, beautiful, playful way, "I think that's loosened it up Annie."

She used two fingers to penetrate my ass to emphasise the point.

I laughed and smiled. She made me feel so relaxed and normal.

"I think it's time I fucked you hard and fast with that blue dildo," she stated with hint of playful demand.

"Jenny, I am so fucking ready for it. Fuck me with it. Just please fucking do it," I said.

The next thing I knew the blue dildo was at the entrance to my ass and Jenny started feeding it in. It was cold and I could feel every centimeter as it slowly slid into me. The further it went it the fuller I felt. Soon both the whopper and the blue ass fucking dildo were all the way inside me.

Jenny stopped and was still for a moment. Then she got a little more side on to me and put her left hand on my shoulder to get a good grip on me. She used her right hand to pull the dildos almost all the way out quite quickly.

"Tell me if I go too fast baby," she said and I heard the care and love in her voice. I felt intensely vulnerable as she held me like that with the two dildos ready to launch back into me. But I also felt loved, safe, sexy and ready to be fucked.

She slid them both gently back all the way in and I couldn't have stopped the gasp of pleasure that came out of me if I had wanted to. She pulled them almost all the way out quicker this time and back in again a little quicker.

The again, out and back all the way in. Faster.

And faster.

And faster.

And faster.

Her hand on my shoulder held me down hard against the couch and squeezed harder with every stroke.

She was hammering away at my ass and pussy as fast as she could and it was so exquisite and I was bucking and desperately trying to fuck back against them with every stroke.

And I had never made so much noise when we'd fucked before. None of it was intelligible. I just moaned and 'oohed' and 'aahed' and 'ughed'.

By the time my orgasm began -- and it took much longer than I would have thought with all of the anal and vaginal sensations and my own fingers on my clit -- I was all but screaming my pleasure.

I could feel that Jenny was getting off on it too. She was muttering, "Mmmmm" and "yeah, yeah, yeah" as she pounded away at me and I could hear the smile in her voice as she enjoyed every minute of it.

When I came I came so long and so hard that all rational thought was completely gone as I wallowed in the intense hard core sexual pleasure of all of the physical and emotional sensations that hammered at me as hard as the dildos.

I was spent and lay still, breathing heavily, face down on the couch with Jenny still holding the dildos inside me. She fell on top of me and pulled my hair out of the way so she could kiss the back of my neck.

The feel of her lips on my neck and her hand between my legs holding in the dildos and the weight of her body on top of me and my hot post orgasmic clit was a comforting and beautiful way to relax and collect my thoughts about what had happened. We lay there like that for a few minutes catching our breath and it was lovely.

When the post coital normality had returned a little I said, "Are you ever going to take those out of me?"

She laughed and got back on her knees behind me. She quickly slid out the whopper a put it aside. Then she slowly eased out the thin blue dildo from my ass.

"I so wish I could fit that inside me Annie. It's not fair. Your finger felt so big in my ass. I could never fit something like that in," Jenny complained with a little sadness. "But I loved your finger in there and I so want to be able to do that too," she went on referring to the dildo she was taking out of my ass.

There's probably nothing she could have said to make me feel better about having shared my anal desires with her. Here she was, wanting to explore her ass and I could be the one to help her. The very thought was heavenly to me.

"Jenny, if you trust me and let me help you I promise you that it won't be long before I'm fucking your ass like that," I reassured her.

Over the next few days we'd make love morning and night and every time I'd finger Jenny's ass. Every time she relaxed more and more and it wasn't long before I could easily get two fingers in her bum.