The Gap in the Curtains Ch. 04

"Are you okay?" I said.

"Sorry, I'm just not used to having anything up there. Your cock is too big, it hurts too much."

"Oh," I said, thoroughly disappointed. "So do you want to just... give up?"

"Well no, but... look why don't you start with a finger or something?"

"Okay, let's give that a try!" I said, with a renewed enthusiasm.

Liz returned to her position on all fours, while I grabbed the KY Jelly and spread some over my index finger. I gingerly touched her asshole, smearing a bit of the lube around the entrance. This was probably my last chance to get this right and I didn't want to hurt her again. I gently pushed my finger into her ass. As my finger tip penetrated her, she flinched slightly, so I stopped and allowed her to get comfortable. I then pushed the finger further in, up to the first knuckle and then the second. It was an interesting sensation. Her ass was tight, yet sort of velvety and the lubricant allowed my finger to slide in quite easily. Liz gave another gasp, but this time it was different. It seemed more like a moan of pleasure than of pain. I pushed my finger all the way in as far as I could and Liz gave out another sharp intake of breath.

"How is that?" I asked.

"Okay," she said. "It feels quite good actually. Try moving it around a bit."

I wasn't sure what she meant by move it around, but I started to move my finger in and out of her ass, like it was a little tiny penis fucking her. Then I tried a few different movements, twisting and slightly bending my finger. Liz gave little encouraging moans as I did do and after a while she brought one hand up to her pussy and started rubbing her clit. Meanwhile I could feel her asshole slowly expanding as it got used to its visitor.

"Shall I try two fingers?"

Liz just nodded and continued to rub herself. I withdrew my finger completely from her ass and re-lubricated it along with my middle finger. Then I held the two fingers tightly together and tried pushing them into Liz's ass. Two fingers are a lot bigger than one and they wouldn't go in right away. But after a bit of work the fingertips went in and then slowly but surely I felt her anal passage expand to accommodate them both together. I watched them slide slowly into her ass with fascination. Five minutes ago there hadn't even been an opening there, but now it had expanded to the width of two complete fingers.

"Aaaaaargh!" said Liz. In my enthusiasm I must have pushed a bit too hard, and my fingers had suddenly slipped completely into her ass.

"Oh shit, I'm sorry, I didn't mean to-"

"No it's fine, just... actually it's... ooh yes like that!" said Liz as I started to move my fingers inside her rectum.

She rubbed her pussy with renewed vigor as I started to pump my two fingers in and out of her ass. Slowly at first, but then increasing my speed as she responded more and more positively. Her sphincter started to periodically contract around my fingers and I wondered if she was going to come.

"Okay, I think I might be ready now," said Liz. "Try with your cock again."

My cock was still erect and had been patiently waiting for its turn. There was still plenty of lube on it and also in and around her ass, but I put a bit more on just to make sure. I aimed my member at her rear entrance once more, pushing it against her open sphincter. The difference between this time and the last was like night and day. The head of my cock slipped easily inside her back passage with comparatively little effort.

"Stop a second," said Liz, clearly still in a bit of pain. She took a few deep breaths and composed herself. "Okay, try pushing it in a bit further, but slowly!"

I took hold of her hips and pushed forward firmly one final time. At last I felt the sweet feeling of my cock sliding into her asshole. Two, three and then four inches disappeared into her back passage. Liz gave out a cry that seemed to contain elements of both pain and pleasure. I held still, waiting for her to give me further indication as I didn't want to hurt her too much. The feeling of her ass contracting around my cock was incredible. It was a totally different sensation from regular sex, tighter than I dared hope.

"Are you okay babe?" I asked

"Yes I'm fine, just... fuck me... slowly, fuck me slowly!"

Liz was panting heavily and trying to speak in between breaths. I tried to do as she asked, moving my cock in and out of her ass slowly and deliberately. I pushed in a little bit further every time and Liz gave out a little gasps as I explored new areas of her anus. It took a while, but after about five minutes of exquisite slow ass-fucking I must have had nearly six inches of my cock inside her. Liz was still rubbing her clit, but she was struggling to brace herself with just one arm. She was obviously getting some pleasure from the experience, but also some pain as well. Suddenly I had an idea.

"Would you like to change positions?" I enquired. "I think if you were on your back it might be easier."

Liz didn't reply, but she rolled over onto her back obediently. I grabbed a pillow and pushed it underneath her lower back, raising her pelvis into the air. Then I gently opened her legs and prepared to get back to work. But before I did, I took a minute to admire the view. Her anus was still slightly open, having not yet returned to normal size after the ravishing it had been receiving. Her pussy was extremely wet, betraying how turned on Liz was becoming.

"My vibrator... in the bottom draw at the back," she said.

I rummaged around her bedside drawer and retrieved her purple egg vibrator. I knew she had it; I used to watch her use it over the internet when we first started our long-distance relationship, but I hadn't seen it since I moved in. I liked to think she didn't have a need for it anymore, but obviously she hadn't thrown it away, so maybe she still enjoyed flying solo every now and then.

Liz switched on the vibrator and the egg started buzzing loudly. She turned a knob on the small remote control, connected by a wire, and the buzzing slowed to a gentle hum. She pushed the egg down into her pussy and started rubbing her clit again.

"Now... fuck my ass some more," she ordered.

I didn't need telling twice. I squeezed a little bit more KY Jelly onto her asshole and watched some of it dribble down inside her back passage. I then lined my cock up with her brown hole again and slipped it in. It took barely any effort at all this time, and I immediately started pumping back and forth. Liz no longer seemed to be in any pain and she was frantically stroking her clit and moving the vibrator around in her pussy. To my delight I found I could actually feel the vibration on my cock through her vaginal wall.

"That feels amazing!" I admitted.

"Oh yes babe for me too," she said.

"I'm not going to last much longer," I admitted, as the vibration and the tightness of Liz's ass around my cock took me towards orgasm.

"Wait for me, I'm nearly there," replied Liz, moving her hand faster over her clit.

I fucked her ass over and over, Liz no longer seemed to care if I took it slow or not. Then I decided to go for broke. I slipped my cock almost completely out of her ass and then pushed it back in hard, burying it completely up to the hilt in her tight butt. Liz let out a loud moan as she felt my full seven inches inside of her.

"Oh yes, fuck my ass, fuck my ass..." she gasped.

I thrust deeply in and out of her ass several times, admiring the unforgettable sight of my cock buried deep inside her nether regions, adjacent to her soaking wet pussy devouring the purple vibrator and her hand flying back and forth across her clitoris. I knew I wasn't going to last long.

"Oh yes, this is it! I'm coming!" shouted Liz.

I wasn't prepared for what I felt next. The vibrating sensation of the egg was suddenly overshadowed by the feeling of Liz's ass tightening around my cock even more. This pushed me over the edge and I felt my orgasm hit me with the force of an oncoming train. I shot my load deep inside Liz's ass as we both came together. I gave a few more strokes, then allowed my cock to fall out of her ass. Liz just lay there on the bed, panting. She pulled the vibrator out of her pussy and threw it to one side. I watched her asshole, still wide open but slowly closing up to its usual size. I collapsed on top of Liz and we both started laughing.

"So how does it feel to get your brown wings?" said Liz

"Magical," I replied. "How was it for you?"

"Painful at first, but eventually it felt really good."

I climbed off my fiancée and threw on a dressing gown. I had to go to the bathroom to wash my junk. It wasn't visibly dirty, but given where it had been I thought it was the hygienic thing to do.

"Hey babe, when you come back I have another hole that needs filling," said Liz as I made to leave the room."

I wasn't sure if she was serious. I hoped not, as I was tired and it would take a while before my cock was ready for another tour of duty. But Liz was always very persuasive when she was horny. I gave my dick a good soapy clean and then returned to the bedroom hoping she would let me off lightly. I needn't have worried. By the time I got back she was already asleep.

_______

I smiled as I recalled the events of that evening, then added 'Attractive', 'Fun', 'Good Sense of Humor' and 'Great in Bed' to my list. It's a shame we didn't have more nights like that. When she let her hair down and was in the mood, Liz was the perfect girlfriend. Unfortunately these days our lives were quite routine most of the time. We would get up, go to work, have dinner, watch TV and then, if we both felt like it, we would have fairly vanilla sex before going to sleep. At the weekend we would usually go out somewhere, but we didn't have as many wild nights out any more, that night at Dillon's had been the only one in weeks. We hadn't tried anal again since then. I suggested it a couple of times, but Liz said she wasn't in the mood. If you include the time when we were 'internet dating', we had been going out for nearly eighteen months now and I had never had a relationship that lasted this long before. Maybe this is how all couples ended up eventually. That was partly reassuring and partly terrifying.

I couldn't think of anything else to put in Liz's column, but I had ten entries now, which was a nice round number. I could always come back if I thought of any additions, but in the meantime I turned my attention to the other side of the page. What were Anne's defining good qualities? Well there was one very obvious one that I might as well get out of the way. I wrote 'Attractive' as the top item in the right-hand column. I started thinking about Anne's model-like looks. Her long silky blonde hair, piercing blue eyes and perfect figure, not overweight but not too skinny either. And her breasts were like... well, like two large firm fruits plucked from the tree of the gods. I crossed out Attractive and wrote "Hot" in its place. But even that didn't seem to do Liz's younger sister justice, so I crossed it out again and wrote "Incredibly Hot".

Okay, so what else could I add to the list? I went back to tapping my pen on the desk as I tried to think. It was a lot more difficult with Anne; I couldn't really pin down the things that attracted me to her other than her superficial beauty. Surely I couldn't be that shallow. I looked back at Liz's list for possible inspiration. Nice? No, that didn't really fly; Anne could be bitchy, narcissistic, rude, lazy and unapproachable. Honest? Not really, only when it suited her. Loyal? I wasn't really sure. Dependable? Grounded? No and no. Fun? I hadn't spent much time with Anne in social settings, but from what I had seen, she wasn't really the life and soul of the party. Great in bed? Well I didn't know yet.

Didn't know yet? It was little mental slips like that which annoyed me. How had I allowed my situation with Anne to get so complicated? It had started off with me spying on her through a gap in her bedroom curtains. Sure it was a bit creepy, but it was a huge thrill and as far as I was concerned a victimless crime as long as I didn't get caught. But then I did get caught but it turned out Anne had a fetish for being watched and she wanted me to carry on watching her. So I did and we were both happy with the arrangement and Liz was in blissful ignorance of what was going on. And then on Christmas Eve I had taken things a little too far and had ended up in Anne's bedroom while she was fapping. And... well, we both got caught up in the moment and she ended up jerking me off, firing my payload all over her beautiful tits.

That was about six weeks ago now. Since then I had tried to stay away from Anne as much as possible, but she didn't make it easy. She started being nice to me. Anne had never actually been nice to me since I moved in. Even during the time we had our 'arrangement', she kept a cool aloof distance from me when we met in the real world. But now suddenly it was like she wanted to be my best friend. She would smile at me, laugh at my jokes and do favors for me. She even started hanging out with Liz and I and inviting us to places, which she had never done before. All the time she kept leaving me notes, inviting me to watch her 'perform' again. Of course it was tempting, but I stubbornly refused every single one. I knew if I was ever in that situation again with Anne then... things could happen, things that couldn't be undone.

And then just when it felt I was in control of the situation, there was... that night.

_______

It was a Saturday; two weekends after the night at Dillon's. Liz and I went out for dinner and then came home to watch a movie. Anne and Vicky, Liz's older sister, were both out with their respective sets of friends so once her parents and brother went to bed we had the house to ourselves. By the time the movie finished and we retired to our bedroom it was gone midnight. Liz completed her overly-long bathroom ritual, while I wondered if I would get lucky tonight. In the end we were both too tried, so we just fell asleep in each other's arms.

It seemed like only a few minutes later, but in reality I think it was more like half an hour, when Liz's phone rang. We both sat up groggily in bed, and Liz groped around on her nightstand trying to find her phone. Eventually she managed to grab hold of it and answer just before it went to answer phone. I could only hear Liz's side of the conversation and in my sleepy state I tried to piece together what was going on.

"Hello"

...

"Oh hey. Do you have any idea what time it is?"

...

"What are you doing over that way?"

...

"But can't you just get a cab instead?"

...

"Okay, I guess I could come over."

...

"Can you text it to me?"

...

"Okay, see you in a bit"

Liz put the phone down, gave a deep sigh and swung her legs over the edge of the bed.

"What was that about?" I enquired.

"It's Anne. Apparently she it at some house party on the other side of town and needs a lift home."

"What? How did she get there?"

"She went with some friends of friends or something, but they've all left and now she's stuck at the party with a bunch of creepy guys, or so she says, and she doesn't have enough money to get a cab."

"And you said you'd pick her up?"

"Well I don't have much choice do I? I can't just leave her there," said Liz.

"I suppose not, but let me go instead. I don't like the sound of this weird party on the wrong side of town and I don't want you going there at this time of night."

Liz looked visibly relieved once I said that. She gave me the address and approximate directions how to get there.

"Okay, I should be able to find it. I'll be about half an hour I suppose."

"I'll keep the bed warm for you," said Liz. "And thanks, I owe you one!"

I reluctantly threw on a few clothes and stepped out into the cold winter air. I really didn't want to be doing this, I was sleepy and cold and I wasn't comfortable with the idea of being in the car on my own with Anne who would probably be drunk. I drove over to the address that Anne had supplied. I tried to make out the numbers on the houses from the road, but it wasn't really necessary as I could hear the party from a hundred yards away. As I got closer to the source of the noise I saw a bunch of guys and a few girls in the street. Most were drinking from bottles and cans and were talking in loud voices to each other. I was glad I didn't live in this street; the neighbors wouldn't get much sleep tonight.

I couldn't see Anne anywhere. I waited for a few minutes but she failed to materialize. Annoyingly I had forgotten my cell phone and didn't have her number anyway, so I realized there was nothing else for it; I would have to infiltrate the party to find her. I silently cursed Anne under my breath for getting me out of bed and making me come all this way to find her. I got out of the car and wandered over towards the house. A few of the guys in the street looked at me as I did so, in what I assume they thought was a tough and menacing way. I wasn't really scared of them; I knew how to handle myself and they were just kids, maybe eighteen or nineteen. I remembered back when I was that age and going to crazy house parties trying to be cool. They were probably just playing at being grownups while their parents were away.

Nobody challenged me as I walked into the house. The inside was dirty and smoky and smelled vaguely of marijuana. There were bottles, cans and chips all over the floor and a pool of vomit lay stagnant in the hallway. It looked like it had been a good party by teenage standards. I followed the voices and eventually found what appeared to be the main party room. There was music playing and about twenty people there, chatting, drinking, dancing and combinations of the above. A couple of them glanced over at me as I came in, but nobody paid me too much attention. I guessed it was one of those parties where nobody, even the person whose house it was, really knew everybody there.

Finally I spotted Anne sitting on a sofa in the far corner of the room. She had a guy draped over her. He looked about the same age as her, maybe twenty or twenty one, with short, black curly hair and stubble and a cigarette in one hand. My knowledge of such things was limited, but he was probably what passed as fairly attractive for a guy that age. Was this Anne's conquest for the evening? I hoped she wasn't expecting me to give him a lift back to our house too. I really didn't want to spend the whole journey watching those two making out in my rear view mirror then have to explain to Liz why I brought a strange guy back to the house.

As I got closer, my perception of the scene changed. The guy had one hand on her naked thigh and was using the other one to stroke her hair. Anne clearly looked uncomfortable, bordering on scared and she flinched at his touch.

"No, I told you, my sister will be here any minute!" I heard her say.

"Sister huh? Is she as pretty as you?" the guy replied.

"Leave her out of this, she's probably waiting outside, I've got to go," said Anne. She tried to stand up, but the guy grabbed her wrist and pulled her back down onto the sofa. I knew that was my cue to intervene.

"She said she has to leave," I said in as authoritative a voice as I could manage." They both looked up and he released his grip for a moment.

"Craig!" squealed Anne, jumping up from the sofa. But her would-be suitor wasn't giving up that easily. He stood up just as quickly as put his hand on her arm in a rough way I didn't like. I suddenly felt very protective towards Anne, and I needed to get her away from here.

"Who's this guy?" he said. "Is he your boyfriend?"

"No, he's my sister's-"