Annie's First LovebyAnalAnnie19©
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.