93 comments/ 370998 views/ 165 favorites Annie's First Love By: AnalAnnie19 This story follows on from "Anal Discovery" (in toys and masturbation) which I wrote about my early sexual awakenings and masturbation. Hopefully this one stands in its' own right but you may wish to read "Anal Discovery" first to get a sense of where my head was at when all this happened. * Cathy had been a friend of mine for years and she asked if I'd like to get out of the family home (in those days still being at home at 20 was a bit dodgy) and move in with her and her friend Jennifer. I liked Cathy and knew her well enough to be sure I could live with her. I had known Jennifer for as long as I'd known Cathy (since the start of High School) but I just hadn't spent as much time with her. I was a fairly enthusiastic masturbator and felt very constrained in the family home -- Mum or Dad walking in on you with your legs open and a dildo at work is a horror beyond thought! So I was very keen to take the plunge. We got this old but nice biggish place with three bedrooms (in those days you could get that for $150 a week). All of us were straight out of home and we had lots of fun enjoying the freedom of doing what we liked in our own house. (If any of my former neighbours are reading this I apologise for the very late, very loud music.) Cathy had a boyfriend so Jennifer and I were happy to have to two rooms at the front of the house while Cathy had the one toward the back that was a bit out of the way (the house was originally a doctors surgery and the room Cathy took was designed to be a bit cut off from the living quarters. It all worked rather nicely. One day I waltzed in to get Cathy out of bed as she seemed to have slept in and I knew she had to get to work and I saw her boyfriend, David's naked ass pumping away at 100 miles an hour as he fucked her. I didn't even know he had stayed over. It would have been somewhat embarrassing but the mad little rooters didn't even notice and I just turned around and pretended it never happened. A few months later Cathy said that she wanted to move in with David and asked if we were ok with that. I think we were a bit uncomfortable with it because Cathy was the one that both of us knew best and we had to adjust to the idea of it being a 'Annie and Jennifer' house as opposed to a 'Cathy and friends' house, but Jennifer and I had become quite good friends so it didn't really matter. Jennifer and I talked about it later on and went to Cathy when I said (reading from a pre-prepared and mutually agreed note), "My dearest Cathy, While it will be of great personal sadness to see you leave our beloved home; and notwithstanding the additional financial burden placed upon us in regards to rent and other outgoings; it is our considered view that the opportunity for you be, at any time of day, in any room of the house, and in every available orifice, heartily, and repeatedly, fucked by the lovely, somewhat attractive and presumably well equipped David; should not be passed up and we wish you well." She laughed, cried, hugged and it wasn't long before she was gone. But there was one very important incident as we were helping her to move her stuff out. I grabbed a box of her stuff from her bedroom to take to David's car when I noticed a DVD in the box which looked a bit suspect. Upon investigation I found it was porn. Now it is worth pointing out here that Cathy was the cool one among us. She knew what to wear and how to talk to guys. She was funny and charismatic and everyone liked her. She had a boyfriend. She was taller and better looking than us. Jennifer and I on the other hand were the nerdy ones. Jennifer had had sex with a few guys but I was still a virgin. In a friendly way Cathy would often always tease us about our clutziness with guys or daggy clothes and general cluelessness. It wasn't in the least bit unkind but Jennifer and I often tried and usually failed to embarrass her in return. She just didn't blush and took all in her stride. I thought I had a shot at getting one back on her so as I was about to put the box in the car and with all four of us there I 'accidentally' (but sort of obviously on purpose) dropped the porn DVD. "Oh, what have we here?" I asked. And in mock horror as I looked at it, "Oh my! What kind of filth and perversion is this? Catherine I'm appalled!" To my mild surprise and great delight Cathy did look just ever so slightly abashed. She reached out to take it and I snatched my hand away. I wanted to prolong this rare chance to torment her a little. "Jennifer will know precisely what to do with this vile filth," I said as I passed it to her. Jennifer took it and looked at the front cover which had a rather graphic image of a couple having sex. She pointed at the image and said, "I hope these two are married!" But Cathy knew how to win these little contests. "You two keep it, I've got the real thing," she said. Now at that point if it had still been in my hand I've have just tossed it back in the box and conceded defeat (or perhaps claimed a respectable draw). But Jennifer said, "Yes I know precisely what to do with this sort of vulgarity." Then she just went back inside with it and we all finished packing the car. A few days later Cathy was gone for good. I did wonder what Jennifer had done with the DVD but I didn't give it that much thought. I guess it was about a week later, by which time Jennifer and I had got used to the new routine of just the two of us sharing the house, when it happened. It was a Thursday night on which day I sometimes went to my parents to catch up with the family for dinner. I told Jennifer I'd be back at about nine and off I went. It was only about five minutes drive away and I had no sooner arrived that I was informed the dinner was off because my sister couldn't make it and Mum was working back. It was no big deal it was a fairly informal thing and we just rescheduled for the following week. Now in all fairness to Jennifer I had said I'd be back about three hours later. Also with moving Cathy out we'd put some furniture in the hallway to clear a bit of space in the lounge to make it easier to lug her things out. We hadn't got around to clearing the hall. Now normally the easiest thing to do was to park in the driveway and walk in the front door and through to the lounge. So normally Cathy would have heard me come through the front door and known I was coming. But I knew the hallway was sort of blocked so I went down the side and came in through the kitchen door. As it happened it was raining so I did what I rarely would and took off my wet shoes and left them in the kitchen. I could hear that the TV was on and I assumed Jennifer would be in there watching. I should have taken more notice of what the TV sounded like but I just didn't think about it. So in effect, what I had done is come around the back and taken off my shoes that would have made some noise and given her some warning of my approach and snuck up on her. I didn't intend to but that's what happened. Anyway I've just bowled in and there was Jennifer naked from the waist down with her jeans and panties on the floor of the lounge room in front of her. She was sitting on the edge of the couch and had her legs very wide open and her right hand rubbing herself very quickly. She was obviously masturbating in full flight. In the other hand she held the remote control and I saw that she was watching porn. On the floor in front of the DVD player was the cover of the DVD we'd taken from Cathy. To that point in my life the closest I'd been to seeing a real person (i.e. not porn) in a sex act was David's bum banging up and down as he fucked Cathy that time I walked in on them. It was extremely confronting and I was a bit shocked. Anyway I took all this in in a fraction of a second and Jennifer jumped up. "Sorry," I said horribly embarrassed, and went back into the kitchen. I felt awful. I knew that if she'd walked in on me like that I'd have been mortified beyond belief. I'd told her I'd be away for a few hours then (albeit accidentally) crept up on her. I got a glass of water and as I did I heard her get dressed and turn off the TV. I didn't know what to do. On the one hand I just wanted to pretend it didn't happen and go in and casually say that the dinner was off and just act like it was no big deal. On the other hand I wanted to tell her not to worry about it and that I really didn't care. But I didn't want to raise it in case it would embarrass her even more. I decided to go back into the lounge and just pretend nothing had happened. I walked in and she was taking the DVD out and putting it back in the cover. She looked fucking awful. The poor thing looked like she just backed her car over my favorite pet. "I'm so sorry," she said, sounding like she had been caught doing something actually bad. She was obviously prepared for me to be angry or something. I felt awful because I was such an enthusiastic masturbator myself and here was poor Jennifer made to feel like a miscreant for just doing what I did nearly every day. I had made her feel like some sort of pervert when she wasn't at all. It was my fault for walking in on her. I took the DVD from her hand. I smiled in the way you would sharing a private joke and said, "You sure knew what to do with that vile fucking filth didn't you." "I think this will have to be in my safe keeping for now," I added. I put it on top of the TV and said, "I'm going to have to watch that myself. Just to make sure your soul is not lost forever. In fact I may need to watch it a few times just to make sure." She smiled and seemed very relieved. "You must think I'm fucking awful," she said, but she sounded a bit better. I put on my most matronly look and said, with my nose slightly raised, "Well if the truth be known I have..." I paused, "...well if the truth be known I have..." I paused again, "... touched myself... you know..." I glanced imperiously at her groin, "... down there...once or twice..." then I changed tone sat down and leaned back with my legs apart and as casually as could be said, "everyday for years on end." She looked me in the eye, "No way?" "Yes way. Every -- single -- day -- for -- years -- on -- end," I said firmly and emphasizing each word. "You're a fucking perverted weirdo," she said in mock incredulity. I was so glad she was getting into the banter. I knew she was going to be ok about it. "At least I do it in my own room," I retorted. As soon as I said it I knew I shouldn't have. All that work to let her know it was ok and now it was all uncomfortable again. I'd hit a bit close to home. I'm surprised at what I said next but I felt that I had done her wrong. I felt I had to undo the damage. I felt a sense of trust with her because she was the vulnerable one because she'd been the one caught with her pants down (so to speak). I felt an enormous empathy for her because in myself I had all of this internalised sexual energy that I felt I could never share with anyone and I would be horrified if people knew about. I wanted her to know that I really was fine about it. And I guess I wanted someone else to know about my own masturbation which had been so important and yet so private a part of my life for so long. "Oh fuck Jenny, don't stress over it. I've got three dildos and two vibrators in my room and all five are showing serious signs of wear and tear. I'm hardly fussed about you doing something everyone does in the privacy of your home when you weren't expecting anyone to walk in on you. I shouldn't have snuck up on you like that. I'm sorry, just forget it," I said. "Anyway when you walk in on me one day we'll be even." "Thanks Annie, I thought you'd want me to move out or something," she said. "Don't be a fuckwit Jenny," I said and that sort of ended the conversation. That night as I lay in bed preparing to masturbate I couldn't get the image of Jenny with her legs open masturbating herself out of my head. The idea that I'd told her about my sex toys was incredibly liberating and the thought that she was probably in the next bedroom finishing off what she had started earlier was unexpectedly very arousing. I just lay there and gently rubbed my clit to an orgasm which came very quickly. I was good and satisfying but I felt there was plenty of sexual energy left in me. In a way I felt I had breached Jenny's trust by thinking about her sexually as I brought myself to orgasm. It was wrong to think of her like that, she hadn't exposed herself to me deliberately. I felt it was disrespectful to her. The usual events unfolded over the weekend. We went out and got drunk with friends and did the usual stuff. I kept thinking about Jenny in a sexual way. At the time I didn't think of it as a gay thing. I just sort of had this background sense that the house was a place where sex happened. And although it was just masturbation it was my masturbation and Jenny's. Here we are two young women sharing a house and we play with ourselves. It just made me feel nice and normal and I really enjoyed thinking about our home in that way. By the following Friday Jenny and I had a few drinks and got ready to go out to a local club. During the past week there'd been the odd masturbation joke between us and a few more of my, as yet not carried out, threats to watch the porn DVD. We were both a bit tipsy and enjoying each others company and watching TV when she said, "You don't really have three dildos and two vibrators do you?" I didn't answer but I gave her a cheeky sort of 'that's for me to know and you to find out' smile. I left it at that but it got me thinking. She had taken the joking a step further. It was a real and specific question about me actually masturbating. Anyway we went out and had a drink too many with our friends without writing ourselves off. The whole group of us had decided to call it a night and were just finishing our drinks when this guy who had been showing some unreciprocated interest in me in the past few weeks came up to try his luck. He said something quite nice and cute which sort of made it hard for me to know how to politely get out of the situation. I didn't want to be rude to him and I am a bit clueless in a situation like that, more so on that occasion because I'd drunk a bit too much. Jenny knew I wasn't interested because we'd talked about him before and could see I was in a dilemma. She looked at the guy and said, "Craig, I'm not sure if you've got the wrong impression here but Annie and I are lovers. Aren't we honey?" With that she kissed me and I kissed her back for a bit of show. There wasn't any tongue involved but it was sexy enough to make a point. All of our friends knew we weren't serious, even Craig knew it was just a joke but it was a nice way to say 'bugger off'. From his point of view I think he enjoyed it a bit. It had just been for show but it sort of felt nice too. It got me thinking. Soon enough we were at home, just the two of us, drinking lots of water to ward off a hangover and debriefing about the night out. I felt comfortable with Jenny and since I'd caught her masturbating I felt that we had broken down the last barriers to talking freely and honestly with each other. I had been very regularly and enthusiastically masturbating for years and in the last year or so in particular I'd been really madly fucking myself with dildos and other toys. I had sort of told Jenny this in the context of letting her know I was perfectly fine with her masturbating in the lounge but that had been a conversation about her not me. And I was fairly sure that my "three dildos and two vibrators" confession hadn't been taken literally. I was just busting to let out my big secret and be open about my sexual feelings and activities. I'd been typecast as the nerdy virgin and I wanted to share with someone that I was in fact a very sexually active -- albeit in a completely solo way. The combination recently catching Jenny masturbating and being half (or maybe three quarters) drunk made me feel like I could just blurt it out to her. I think also the fact that she'd kissed me earlier in a pretend sexual way was a further indication of the fact that we liked and trusted each other enough to be talk about anything. It wasn't that the kiss was a lesbian thing; it was just that it was another element contributing to my sense of being able to be open with her. I really wasn't thinking about Jenny as a sexual partner. I was thinking of her as a best friend I could confide in by sharing a happy secret. I felt bold and so I said, "I think it's time I had a look at that vile filth that has perverted my friends." I walked to the TV, grabbed the porn DVD and put it in the player. When I turned around Jenny looked a bit uncomfortable and I had second thoughts about talking to her about myself. I really didn't want to freak her out and I decided to just make light of it all. There was the usual appalling story line and ridiculous female characters which gave me an opportunity to joke about it (I mean who wants to be called a slut and have their ass spanked during sex?) I skipped that scene and said, "He's ugly, skanky and nasty -- let's see what else there is." "Yeah, he is so fucking gross," Jenny said, agreeing. The next guy was much better looking and I said, "That's more like it." "Mmmm. It certainly is," she agreed with a healthy twinkle of lust in her eyes which made me feel much better about having put it on. As time went by watching the sex became quite entrancing and I started to get very horny. We both sat there quietly and just watched. It got to the point where I was almost shaking with lust. I had an incredible urge to just touch myself then and there. It was so overwhelming that I wished I hadn't put the damn thing on. I felt like I'd lost control by being so horny at an inappropriate time. I could stop myself watching but I just had to do something, I had to get up and get myself away from the lounge and make myself come. I found myself deliberately squeezing my legs together and minutely moving my hips to gratify myself in some small way. It was very confusing for me. On the one hand I was intensely aroused. On the other hand I felt that I was behaving really inappropriately by being so captured by lust in Jenny's presence. It was torture and it was fucking awful. I decided that I just had to go to my room and masturbate and get away from the horrible confusion. Twenty minutes ago I'd have just said "I'm going to masturbate now" and walked out but now I was so buffeted by lust and worry about being inappropriate and confusion that I didn't feel open and couldn't think straight. I became conscious of Jenny, what would she think if I just walked off? She'd know I was going to masturbate -- was that OK? As I thought about it I noticed that she was sitting forward on the edge of the couch, transfixed by the sex on the screen. Her legs were held tightly closed. Her hands were clenched into fists by her side. She was leaning forward like she was trying to hold on to a piss. I thought, "She's as horny as hell and she's just like me sitting here thinking, 'I need to touch myself!' just like I am." It was a great relief to me and I managed to dig myself out of my internalisation and I slowly began to feel more and more like talking about masturbation to Jenny. I didn't know quite how to broach the subject but I really wanted to again. The scene at the time had a girl and two guys. She was being fucked doggy and was sucking the other guys' dick. Jenny said, "Greedy bitch, one of those would do me very nicely right now." And then I said what I'd been wanting to all night, "Yeah. I'll have to settle for a rubber one tonight." There. It was out. I said it. Annie's First Love I looked at and pretended to be totally focused on the TV but all of my attention was on Jenny and her reaction. I wanted her to probe my comment. I wanted to tell her everything. I sat back and opened my legs to a normal sitting position sort of degree. To punctuate my point, to make it clear that I was openly telling her I was going to masturbate tonight I calmly put the palm of my right hand on my pubic mound and put my four fingers between my legs and gave a gentle but distinct squeeze. I can honestly say at this point I wasn't thinking about Jenny in a direct sexual way. But I was desperate to talk to her about masturbation and my sex toys. I needed to share it all with someone. She looked at my hand in my crotch and then directly at me, "Have you really got one?" she asked flatly. This time it wasn't a gently curious question as it had been earlier in the day. It was a serious question. She asked it in a way that said 'tell me the truth now'. "No. I told you. I've got three," I responded equally flatly looking her directly in the eye. "And two vibrators." The seriousness in her eyes turned into a twinkle of excitement. It was like that look someone gives you when you've a box of chocolates, or free tickets to something. She said just one word. I didn't expect it but it made sense. It was the most exciting thing she could have said. It was said firmly but with a smile. There was no room for compromise. It was a demand. "Share." I felt wonderful. I wasn't just going to talk to her about my toys I was going to let her see them. I didn't say anything. I just got up and walked toward my room. I grabbed my shoe box of toys from their hiding spot in one of my drawers. I took out my vibrating butt plug and the little finger width vibrator and my smallest dildo and left them in the drawer. They were for anal play and while it was exciting to share my toys with Jenny anal was a taboo I wasn't ready to cross. That left the three dildos and two vibrators. I also left the lube in there even though I mainly used that for anal. I was so sexually excited that I just had to touch myself before going back into the lounge. I stood with my legs open and the shoe box in one hand and rubbed myself through my jeans with the other. It felt great but created more lust than it relieved. My jeans were so tight and I was so wet that it felt a bit uncomfortable. It was fairly common after a night out for one or both of us to take off our jeans and just hang about in our knickers and shirt. I put the box on my bed and took off my jeans. I stood with my legs apart and touched myself between my legs. I was incredibly wet and it felt fantastic to fell myself through the much thinner barrier of my panties. In was taken by lust and pulled my panties half way down my thighs so I could touch my clit skin on skin. It was lovely but I didn't do it for too long. I was about to pull them up again when I decided to take them off. I thought to myself that with the long shirt on Jenny need not know but in reality this was the most provocative thing I did all night. I wouldn't have done it if I wasn't so sexually aroused and to be honest, drunk. As I walked down the hall back to the lounge I felt incredibly sexy with my vagina bared (albeit hidden by my shirt). I also felt nervous. The moment had come where I would share something of my sexual feelings with another person. I didn't really know what would happen when I showed them to Jenny, I was just excited to show them to her. I suppose I was thinking that we would talk about them and hopefully how I used them. Something like, "Oh, I love using this one on my clit when I fuck myself with this one." I suppose I thought she'd ask how long I'd had them and where I got them. I thought it would end with her borrowing a couple and we'd each retire to our own room. But that doesn't explain why I was deliberately very quiet when I walked along the hall. It doesn't explain why I almost peeked around the corner hoping to see her fondling herself. She was sitting back with her legs slightly apart and her hands, palms together between her legs. She didn't seem to be moving much but she was rubbing herself sexually if very slowly. I was very excited about showing her my goodies and I held the box with both hands close to my body and I walked in. She looked at me noting my naked legs but stared at the box. "Oh, no way!" she said, obviously meaning the opposite. I walked around the coffee table and sat close to her on her right. Close enough that our hips and shoulders were touching. Right nest to each other as you might to sit and share a box of chocolates. I sat the box of toys half on her lap and half on mine. I lifted the lid and looked at her face. She peered in and I said, "Three dildos and two vibrators." She looked in and saw my toys. She had a sort of 'you little beauty' look on her face and said, ever so softly "Oh, wow." I grabbed one of the vibrators out and cranked it up to full, "Have a feel of that," I said, handing it to her. That was bolder than I had intended to be. As soon as she grabbed it she said, "Oh, fucking hell, Annie! That is so hot!" I don't know what possessed me when I grabbed the other one. I guess the look on her face and the way she talked and the feeling I had that she was really happy to be able to use my toys broke down all of my inhibitions. I hadn't planned to do it. While she was still holding and marveling at her vibrator I cranked up mine, put the box on the coffee table and turned my head towards the porn on the TV. I leant back and opened my legs and lifted my shirt to expose my bare vagina. I kept my eyes on the TV and put the vibrator against my clit with my right hand. I was looking at the TV but again all of my attention was on Jenny. I was at once terrified that she'd think I was a weirdo and intensely sexually gratified by the vibrator on my clit. She immediately put down her vibrator and stood up. For a split second I thought she was going to walk away and I took my vibrator away from my clit and my face was red before I realised that she was just standing up to get her jeans undone. In one go she pulled her jeans and panties down to her ankles. She sat back down, kicked her jeans and undies off and had her vibrator on clit straight away. "Oh my god that feels fantastic," she said in a loud, upbeat and confident way. "I can't believe you have been keeping these to yourself this whole time you mean, nasty, selfish, unsharing cow." I looked at her public hair and watched her work the vibrator across her clit and back. It was fascinating to watch and I couldn't take my eyes off her. She kept her head forward and watched the porn. I put my left hand up under my shirt and fondled my breasts through my bra. I started to hump my hips gently and with a low, "Oh, yeah," I opened my legs wider. As I did so I deliberately made sure I rubbed my left leg against her right leg but in a way that could have been construed as accidental. I can honestly say that at this point I still wasn't overtly thinking about Jenny as someone I wanted to have sex with as such. I just wanted to touch her in a way that would make me feel closer to her as a friend because we were sharing this moment together. As soon as my leg rubbed against hers she lifted her own leg up and I again thought I'd gone too far and she was moving away to avoid the contact. But no sooner had she lifted her leg up than she put it back down again on top of mine. She sort of used her leg to hook mine and pull my legs further open. She also shifted her body so that we were snuggled closer together on the couch. The sensation of her flesh against mine was overwhelming. It was the first actively sexual touching I'd felt that wasn't done by myself. It heightened my sexual pleasure enormously. It felt so much more complete than masturbating alone. I had to have more and I took my left hand from my breasts and grabbed her thigh and squeezed my approval. She immediately responded by swapping hands with the vibrator and putting her right hand on my arm and squeezed approval back. I put my hand on her inner thigh and pulled it towards my body. Together our breathing intensified and it was incredibly affirming to share my sexual excitement with Jenny. I pulled her leg close to me, lifting it up and hugging it to my body as we both kept masturbating with the vibrators. I had never experienced the sensation of someone's orgasm building with mine and it was incredible. I could hear her breathing becoming a pant and my own breathing followed suit. I could see the vibrator against her clit and see her back arch. I could feel her tense up and feel her move as her hips began to hump spasmodically. I could smell her sex and mine. Hearing, seeing, feeling, smelling the sensations were overwhelming. Until that moment I hadn't understood the notion of "coming together". It wasn't just that we came at the same time. I didn't slow down to let her catch up or speed up to catch her. I didn't have any control over it; my body just synchronised with hers; the sexual energy built and climaxed in unison. We came together with her right leg entwined with my left. My left hand squeezing her leg and pulling it toward me. Her right hand tightly gripping my forearm and squeezing hard. Our other hand holding our respective vibrators on our clits and humping our hips together. It was an intense orgasm for me. Not one of those ones that you ride through and consciously savour. It was one of those ones you have no control over that rip through you before you know what's happening. It gripped me vice like and I involuntarily shuddered as it racked my body. Afterwards I was dazed and it took me a minute or two to comprehend what had just happened. I couldn't quite reconcile it with my life up to that point. Something would never be the same. In a way I had lost part of my virginity. Not technically but psychologically. I had shared a sexual experience with another. We disentangled, turned off the vibrators and shared a conspiratorial giggle. I felt very relaxed and with a very big smile said, "That hit the spot." "Oh, indeed. Very fucking nicely indeed," she replied. I used my shirt to dry off the end of my vibrator and casually tossed it back into the shoe box. I then took the other vibrator of Jenny and also cleaned it off with my shirt. I felt by doing so I was entrenching the mutual nature of what we had just done. I wanted to emphasise, to myself and Jenny, that it was a shared act. To my way of thinking at the time wiping her juices onto my shirt said very clearly. I think I also wanted to encourage Jenny to be relaxed about the toys. By being so casual about their use and handling I hoped to do that. As exciting and fulfilling as it had been I think we both needed to be alone to think about what had happened and it was late and we'd had a lot to drink and so we soon went to bed. I drifted off to sleep fondling myself and thinking about what had happened. In the morning I got up first and had a shower. I didn't masturbate because I had a sort of sense of expectation. I wondered if we'd be in for a repeat performance that evening. When I got out Jenny was eating some toast in the kitchen watching TV. She greeted me with a sort of silly, chirpy, "Lovely morning my dear." "You pulled up alright," I said because she didn't look or sound hung over. "Yeah, how 'bout you?" she asked. "Fine. I reckon all that water did the trick," I answered. We chatted over breakfast about this and that for a while and then I said, "So you liked my little box of goodies did you?" "Oh fuck yes, Annie," she replied. "Very much so as it happens. I hope you realise I expect to be able to borrow them from time to time." "Naturally," I said. "I'll show you where I keep them and you can help yourself whenever you like." With that I got up and headed to my room with Jenny in tow. Once in my room I got the box out of the drawer. "Here they are," I said and handed her the box. "Oh, wicked!" she said happily. She took off the lid and grabbed my biggest dildo. It wasn't giant sized but it was pretty big. I didn't use it all that often but once in a while I just wanted that feeling of being stretched and really full. "Christ almighty, Annie. Do you actually use this whopper?" she asked. "Sometimes I do. Sometimes I really give myself a good hard fucking with that one," I answered. "Liar. You do not," she teased. "It wouldn't fit inside your tiny little virgin vagina." I just looked at her for a moment. The way she had said that was just asking for me to say, 'Do so.' It was obviously going to end up in a playful, 'do not,' 'do so,' 'do not,' 'do so.' That in turn was obviously going to end up in either an, 'Oh yeah, well watch this' from me or an 'Oh yeah, well prove it' from her. It was our usual playful banter but she had in effect said I want to watch you use this big dildo. She may not have thought through the implications that bluntly but that's what had just happened and I think we both realised it at the same time. I held my stare for a moment longer. All either of us had on was a dressing gown. I keep looking her in the eye and untied mine and cast it theatrically aside. Again I held my stare for a moment before grabbing the big dildo. I held it before me in front of her as if to say, 'Exhibit A.' I took the lube and held it in my other hand in the same way. I dropped my gaze to the exhibits, upended the lube a squeezed out a big blob onto the head of the rubber cock. "My dear, dear, Jennifer, you really must not persist with these doubts. Have I not proven that when I tell you I have three dildos and two vibrators I indeed have them. When I tell you I give myself a good hard fucking with a large silicon phallus that is precisely what I mean. Now you have simply forced me to demonstrate. Please observe as I eradicate any vestiges of dubiety that you may still harbour," I said. I guess I had been playing around with the mock formality as a way of avoiding the more intimate route which would have to have been to tell her how excited I was at the thought of sharing my toys with her again. To say I was sexually excited would be an understatement. But this wasn't just about physical sexual excitement. It wasn't just about the thrill of anticipation at the penetration. It wasn't just about making myself come. More than those things it was about sharing my journey of sexual awakening. Look at me, I have found these ways to feel really good. I want to share it with you, I want you to see how I feel, I want you to share my joy. Everything about my sexuality that had been locked up inside was flooding out. That was really what excited me so much. But that itself supercharged the sexual energy. Sometimes when I touch myself my mind is ahead of my genitals. I have a mental lust that my body has to catch up to. Sometimes it's the other way around. Before I even touch myself I know I'm almost ready to come. This was one of those times. I had thought I was going to just lie on my bed with my legs open and slowly engulf the dildo as I watched her reaction then start to really pump it fast so I could "really give myself a good hard fucking" as I had promised. But by the time I got to the bed, lay on my back and spread my legs wide I was so aroused that I was frantically rubbing my clit straight away. Of course as soon as I started doing that I was completely captive to the intense lust I felt. I was close to the edge of the bed with my knees wide apart and pointing straight up. My feet were tucked up close to my bum. I pushed the dildo in faster than I normally would to show off and it wasn't more than a few strokes in and out before I was hammering away at top speed. My right hand worked the dildo and my left worked my clit. Jenny put the box of toys on my bedside table and let her dressing gown drop to the ground. She was gently fondling herself between her legs as she came over to me. She was spellbound watching me and came and sat on the edge of the bed to my right. She was very close to me and sat so that my right leg was across her lap. She used her left hand to rub inside my thigh, which I found astonishingly sexually gratifying. I couldn't exactly see but it was clear she still had her right hand between her legs. I was quickly approaching orgasm and as it became obvious she shifted position and was now facing me side on with her left knee up on the bed and against my side. Her right leg was still on the floor so her legs were now very open too. I could hear the sound of her fingering herself which turned me in inordinately. I could feel the orgasm starting and it must have been obvious to Jenny because she seemed to get more excited too. She pushed herself closer to me and stopped rubbing my inner thigh, instead using her left hand to fondle my breasts. When she started gently working my nipple between her thumb and finger I went fucking wild. It was partly that it felt so damn good but I think more significantly it was that she was very definitely sexually gratifying me. Up until that point the thigh rubbing and the touching the night before had all been affectionate encouragement rather than direct sexual stimulation. I couldn't help but say, "Oh fuck yes, yes, yes. Jenny ... oh .. yes." Before I knew it I was coming and Jenny grabbed my right ass cheek with her right hand squeezed hard -- I could feel the wetness from her own juices on her hand -- her left hand still worked at my nipple. And her lips were on mine. We kissed passionately and I came intensely as our tongues caressed. At that moment I learned where the term 'making love' comes from. When you come like that, close to someone who is part of the sexual gratification, touching, caressing, holding, squeezing, feeling them against you, intimately entwined, there is a powerful rush of emotional feeling for them. I had to suppress the natural instinct to say, "I love you." I guess in that moment, with that kiss we became lovers. As the thrill of the sex abated and the orgasm subsided I felt intensely happy and relaxed. I shifted position as I withdrew the dildo from my vagina and Jenny lay back on the bed next to me. I rolled onto my side to snuggle up and presented it to her, "Believe me now oh ye of little faith?" She smiled but it was more a polite smile than joining in on the joke. I was momentarily puzzled until I saw the clear and unmistakable lust in her eyes and noticed that her breathing was still a little ragged. She hadn't come and she was still very horny. I felt so selfish. There I had been getting off and having a great time and as I was coming Jenny had both hands and all of her attention on me. I was a bit embarrassed to have been such an inconsiderate lover. Now I suppose there really are some people out there who come three times in a row and still feel horny immediately afterwards. Well if so I'm not one of them. Once I've come my sexual desire subsides and while I can be at it again as soon as 15 or 20 minutes later I'm just not captured by lust straight after I come. That's why I was so surprised at how I felt seeing Jenny lying there in lust. I had an urgent need to touch her and satisfy her. I felt my chest tighten, my breathing became shallow and my stomach tensed. I was having all of the ancillary physical responses to a state of lust but no corresponding need to gratify my own genitals. My compulsion was all to gratify her. "Now let's see how your tiny little vagina copes with the whopper," I teased and this time she smiled wide in a sort of 'oh yes, yes, yes' way. She lifted her knees right up and her legs wide apart. Annie's First Love I got off the bed, stood in front of her and still holding the dildo in one hand grabbed her thighs close to her belly so I could get a good grip and pulled her right to the edge of the bed with mock roughness. I took hold of her right leg and held it straight up against my body with my left arm, hugging it close. She kept her left knee bent and her leg wide open. I took hold of the dildo close to the end and massaged the head up and down her labia and clit. "Really Annie," she said in a tone to let me know she was serious, "be careful with that thing, it might be too big." And referring to the way I had just penetrated myself added, "Don't push it in fast like you just did." I definitely didn't want to do anything to hurt her and thought about getting a smaller dildo. But although she was clearly a little frightened she was obviously in desperate need of gratification and I thought there was also an implicit desire to try the 'whopper'. I put the head against her opening and gently pushed with a slight twisting motion to ease it in. She responded by slightly pushing back to let me know it was alright. I paused and brought my left hand down, still with my arm around her leg, and began to gently fondle her clit. She got much more excited and arched her back a little and very unselfconsciously started to tease both nipples between thumb and forefinger. It was thrilling to see her getting herself off like that. As I eased the head of the dildo further in her mouth and eyes opened wide and she gave a small jolt as the full width finally went inside her. I was worried about her and said, "Is that OK?" Her words came out one at a time and very slowly, "... oh ... it's ... so ... fucking ... big... oh ... fuck ... yes ..." I gently fed more of it into her and she kept up a steady but tiny humping motion against it. I got on my knees so I could be closer to her and I cuddled my head against her thigh as I rubbed her clit and kept easing the dildo slowly further in. Finally it was all the way in. Seeing her like that, swamped by desire and vulnerable and beautiful made me want to be so gentle and caring and loving towards her. I wanted to do anything I could to please her. I was captured not by my own lust but by hers. I kissed her inner thigh more as an expression of love than to gratify her. I heard her give a sharp intake of breath and realised that my kiss had implied something else. I didn't want to disappoint her. I kissed her again, this time further up her thigh and felt her push against the dildo. I started to gently work it in and out of her as I kissed my way closer and closer. We were soon in a rhythm and I was fucking her with the dildo and she was fucking it back. I took my fingers off her clit and replaced them with my tongue. She started to moan and talk and was saying things like, "yes" and "oh fuck yes" and "fuck fuck fuck fuck fuck" and "please". But most of all, and most deliciously, she was saying, "Annie, Annie, Annie." It was heavenly. It was so 'in my face' so to speak. She was so close to me and so into it and I was assaulted by the taste and smell of her sex and the feel of her clit on my tongue and her pubic hair in my face and she bucked so much I had to use my left arm to squeeze around her right leg and stop her slamming into my lips and teeth and face. I pumped her faster and harder with the dildo and put all my weight into keeping her still so I could lick her clit furiously. I don't know how long I fucked her and licked her like that but it seemed that with every moment she got even more excited and when she eventually did come it was such a release for both of us. The knowledge of her orgasm racking through her body as I licked and fucked her was fabulous. I had such a sense of a job well done and I felt my earlier embarrassment at being a selfish lover completely wash away. I felt like I was a special person for having been able to take her to such a special place. I felt like I was a good lover and I felt very proud. Once the rush of it all had subsided I slid the dildo out of her and got up and lay on my side on the bed next to her. In the most nonplussed manner I could conjure I casually said, "Seemed to fit OK," as I brandished the dildo before her. She took my face in her hands and said, "You wonderful, beautiful, crazy, muff diving lesbian." And she kissed me and I kissed her back and we hugged. As we lay there together with our spent, naked bodies against each other I felt so close to her and so happy. It was like all of my sexual internalisation of the years gone by and the barriers I had worked so hard to keep up came crashing down. I felt liberated and I realised how alone I had been up until that point. I don't think either of us yet knew exactly how we felt about the fact that we'd just had sex. But I knew I wanted to do it again and I felt relaxed enough with Jenny to just say so. "I really enjoyed that," I said seriously but without being heavy about it. "Do you want to do it again sometime?" I hoped my tone was such that she would know it was OK if she didn't want to. "Do I want to do it again sometime?" she repeated. "Sometime! Are you fucking joking? I want to do it every day -- fuck that twice a day -- from now on. God all fucking mighty Annie with your three dildos and two vibrators -- not to mention that tongue of yours -- I'll never need a man again! Fuck Annie. SOMEtime!" She sat up and took me by the firmly shoulders and shook me, "Don't give me that fucking 'sometime' shit, girl, you and I are going to do it again ALL the fucking time. Do I make myself clear!?" "I think I'm getting the general gist of where you're coming from my dear lascivious friend," I replied. The day went on as normal and we did the grocery shopping and a few things like that. There were two things that nagged at the back of my mind. Firstly, was I really a lesbian? I had never thought I was before and I looked at men and I lusted after the sexy ones. But I had certainly had great satisfaction in making Jenny come. I looked at her and I thought she was beautiful. Thinking about her body and vagina and clitoris and breast and nipples and lips made me respond physically with a hardening of my nipples and a tingling in my genitals. The other thing was anal sex. On one hand I really felt open and trusting with Jenny. On the other I just could bear the idea of telling her I liked playing with and putting things in my ass. She would think it was disgusting and that I was disgusting and I just didn't want to wreck what was happening between us. Later in the afternoon we were both kicking back watching TV and taking it easy. There came a point when there wasn't much on to watch and nothing obvious that needed doing. I wanted to raise the idea of having sex and I thought Jenny was thinking about it too because it was just a tiny bit awkward. "Not much on, nothin' much to do, might just pop that DVD on whadda ya reckon?" I said as a slightly less direct way of bringing it up. Jenny sprang into action. We both knew it was possible that friends could drop by so she said, "I'll get the DVD on and pull the blinds down. You lock the doors and get that box of goodies." In about 60 seconds we were both naked on the couch and the toys were on the coffee table in front of us. We skipped past the scenes we'd watched the night before and started watching one with a nice looking guy and a rather petite redhead. We sat next to each other and used one hand to fondle the other between the legs and the other to tease our own nipples. I was startled at how different it felt to have another person 'at the controls' as it were. It was far more intensely gratifying that I could ever have expected. As we watched the redhead was swallowing the entire length of the studs whopping dick. "How do they do that without gagging?" I wondered out loud. "I know, it's incredible isn't it?" she responded. Although we were both really enjoying ourselves we had by unspoken mutual agreement decided to make this a nice long slow session and we took our time as we gently fondled each other and watched the porn scene progress. Soon the tables had turned and the guy was going down on the girl. "He's not as good as you," said Jenny playfully. "Goes without saying," said I. "Question is my dear, how good are you?" I added with raised eyebrows and a hint of a challenge. "You'll see lover. You'll see," she promised. "Sooner rather than later I hope," I said. "All in good time my dear, all in good time," she teased. Once the guy started to fuck the girl Jenny said, "Oh fuck yes. Dildo time." We grabbed the box and Jenny took one of the medium sized dildos. "Not the whopper?" I questioned. "Don't get me wrong it was great but it's just a bit too much you know," she said. "Yeah I know what you mean, I don't use it too much myself. What with having a tiny little virgin vagina you know," I said. "Looked like you had a bit of experience this morning," she teased. We resumed our positions fondling each other but this time using our spare hand to fuck ourselves with a dildo each. It all got a bit much for me and I was very quickly in the sex crazed zone, unable to think of anything but sexual gratification. I started to fuck myself harder and move my hips back and forth to the rhythm of the dildo and Jenny's fingers on my clit. It was so wonderful to feel someone else's touch! She must have sensed that it was all getting too much for me and she kept one hand holding her dildo inside her and one on my clit as she leant forward to look into the toy box. She close her legs to hold in the dildo and grabbed a vibrator. My hand lost contact with her sex as she got off the couch and onto her knees in front of me, still holding her legs closed with the dildo still inside her. She had to stop fondling my clit to twist on the vibrator but I couldn't bear to be without the clitoral stimulation even for a second so I started to rub myself as well as masturbate the dildo in and out. She was luxuriating in watching me get myself off. "Annie, it is such a turn on to watch you do that and to think that you have been doing it in your room the whole time we've been living together," she said. That just spurred me on and I fucked and rubbed harder and faster. Jenny opened her legs and let the dildo ease out and drop to the floor as she applied the vibrator to her clit with her right hand. She used her left to rub my thigh which egged me on more to show her how I fucked myself and made myself come. I though she was just going to watch me and I was turned on by the idea of her seeing me come like that. But she wasn't just going to watch. She took hold of the dildo and began fucking me with it as I kept rubbing my clit. I used my liberated hand to work my nipple and watched her face as she became entranced by looking at my vagina being fucked by the dildo she held. I suppose the lust, dare I say hunger, in her eyes should have warned me but when she suddenly dove her face between my legs a thrilling jolt of anticipation shot through me as I realised she was going to lick me. I got my hand out of her way and now had one for each nipple as she continued to fuck me with the dildo in one hand and hold the vibrator on her clit with the other. Having Jenny's fingers on my clit had been very exciting but the feel of her tongue was nothing short of exquisite. It was so soft and felt so perfect in the way it massaged my clit. I had never really fantasised a lot about oral sex but I now knew why people loved it so much. Her mouth was so perfect for stimulating my clit and surrounds. The gentlest touch of fingers or a dildo is rough compared to the sweet caress of soft lips and a flickering tongue. As Jenny gratified my vagina and clit I felt an enormous up swelling of adoration for her. Having her head between my legs like that, so intimate with my body, so linked to me in such a private way, I just wanted to take hold of her and squeeze her and kiss her. I wanted to reciprocate but all I could reach was her head so I put my fingers in her hair and caressed her scalp. "Jenny, Jenny, oh fuck, oh fuck that is so fucking good. Jenny, oh fuck, Jenny," I said with my voice thin and feeble from lust. She responded by licking me faster and fucking me even harder and I started to feel an orgasm rising in me from deep, deep inside. When the orgasm struck it was hard and sharp and fast. Sometimes orgasms rack your whole body but this one shot all of its intense energy through my clit to a degree that it was almost painful. As the peak quickly smashed through and over me I realised that I was squeezing Jenny's head with my thighs and crushing her head with my hands. She was still licking my now post orgasmically hyper sensitive clit and I quickly released her head to give my clit the space it needed to recover. As I looked into her face I could see she was in a state of post orgasmic bliss herself. The vibrator had done its' job. She smiled at me with a self satisfied grin. But this was no laughing matter I was still desperate to hug and kiss her and I dragged her up onto me and kissed her passionately. The taste of my sex on her mouth added to my sense of intimacy with her and I hugged her tight and rubbed my hands over her naked back and squeezed her ass cheeks before snuggling my lips against her neck to kiss her. She could see that she had really done something special for me and looked happy and proud. "Like that did you?" she asked with profound understatement. "I just had no idea how good that was going to feel," I answered. "I thought you were going to suffocate me you crazy bitch," she said. "Not intentionally, my dear. You are proving to be quite valuable alive as it happens," I replied. We put the toys back in the box and got dressed. I took the box back to my room and Jenny followed. As I put them in the drawer she said, "By rights I should have some of those in my room." "I'm sorry, I know I said you could help yourself anytime but I've changed my mind. I've seen you at work with these things and I'm worried you might over exert yourself. You can only use them under appropriate adult supervision. Me being the appropriate adult of course," I said. "Right then. So what you are really saying Annie, is that in order for me to access the basic right, the most basic human right, that every woman has to vibrate her clitoris and insert a dildo into her vagina, I have to perform acts of lesbian sex with you?" she responded. "I think that is a reasonably accurate summation, Jenny," I said. "Does that make us official lesbians then?" she asked. Her tone was more serious but also had a note of intellectual rigor about it. "Excellent question," I answered. As we walked back to the lounge we began a dissection of the question. "We are both women," I put forth. "Agreed," she acknowledged. "We are fucking each other," I asserted. "Agreed," said Jenny. "We intend to continue fucking into the foreseeable future?" I asked. "I'd agree with that too," said Jenny. "Certainly fucking hope so anyway." "Yes indeed," said I. "Now there's no doubt that the ongoing fucking of one of the same sex does raise a valid question about the sexual orientation of the said fuckers," proffered Jenny. "Yes, raises the question. But is it not true that the nature of ones sexuality resides within their heart and mind and is not determinable by the action of the body?" I responded. "Perhaps," Jenny conceded, "but I for one could not contend that I do not lust after you my female friend." "Nor could I," I agreed. "So does that mean we are out and out lesbians or must we at this stage only conceded a degree -- a degree yet to be determined -- of bisexuality?" she asked. "I think at the least we have to concede a degree of bisexuality," I said. "But we'd only qualify as fully fledged lesbians if we had no desire to fuck men." "I think it has been established that I like to fuck men but what about you Annie? Is your virginity a result of a secret lesbian sexuality?" she asked. "I'd say my virginity is more a failure of the opposite gender to produce someone sexy, kind and intelligent -- and not to mention available -- all in the one person," I answered. "OK, so you got Ken and Barbie," said Jenney referring to the nick names of a couple we knew who were both gorgeous, "both naked, both willing and available. Who do you jump?" she probed. "It's gotta be Ken," I said with confidence. "Is that just because you haven't had a guy fuck you before though?" she cross examined. "Nope. I mean she very good looking no doubting it but he's the one I'd fuck every time," I answered. "I do look at you and find you sexy. I do look at you and feel aroused. I do lust after the idea of doing it with you but Barbie just doesn't do it for me. Other women don't do it for me. You just do it for me." "OK well I've got to confess I'd jump Ken say seven or eight times out of ten but I'd have a crack and Barbie the other two or three," confessed Jenny. "OK well I'd have to concede that even though Barbie doesn't do it for me maybe if there was another woman who was my bestest friend in the whole wide world who I adored and caught masturbating in the lounge room -- who knows maybe I'd want to do it with her too," I said. "I think we've got it solved Annie," she said with some confidence. "We're both a bit bisexual." "Well fuck me," I said. "If you told me that on Thursday I'd have thought you were a fuckwit. But I gotta concede I think you're right." We fucked like mad for the next few weeks. We often shared a bed and tried everything twice and the fun things we just had to keep practicing. We became very close and although neither of us said it I think we both knew we were in love. We had really been focusing on exploring each other and had hardly watched the porn DVD. But one night after we got back from a night out with friends we ended up putting it on again. We had had sex earlier in the day and so there wasn't a hungry rush to immediately touch each other and get the dildos into action. It was late and we were relaxed from the alcohol we'd consumed in moderation. We both ended up in just our knickers -- I don't know why we hadn't taken them off -- and we hadn't even got the toys out. I was sitting in the corner of the couch leaning back and gently masturbating myself with my legs apart, one leg up on the couch and the other on the floor. Jenny came to me and we kissed and caressed each other and we snuggled together with her head against my shoulder, her right arm around my back and her left hand teasing my nipples. I had my left arm around her neck with my hand cradling her head. With my right hand I played with her breasts and nipples. We reclined like that and watched the action unfold. It felt very intimate and although we were stimulating each others nipples it was as much an affectionate embrace as a sexual one. We got to a scene in the porno that neither of us had seen when the next thing I knew the porn girl was on her knees and the guy was fucking her doggy and she said, "Oh fuck that's a big cock. Let's see how big it is in my ass." I was turned on as he slowly pushed his big dick into her ass and started pumping away but I just didn't know what to say or how to react. I had wanted to tell her about my anal desires and masturbation but I was frightened that she'd think I was a weirdo and I'd ruin everything. In one way I felt terrible about not telling her, like I was being dishonest with her. I really was very comfortable in myself, or at least I thought so, with my anal desires and activities. But I couldn't imagine telling even Jenny about it partly because it was a fringe sexual activity but also because I loved it so much and that heightened the perversion of it. It would be one thing to be a bit into it but to relish it as I did ironically made me feel more privately about it. 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. 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.