We were on our third drink when the questions started. This was always the way with Sienna, a few cocktails and the ‘naughty’ inquisition began. I always thought it was funny that a few martinis could wash away her preconceptions but I guess that’s the way with anyone.
With Sienna though it always came down to the same line of questioning. Anal sex. I’d told her once that I was quite into it and since then it had become her favourite drunken conversation topic.
Why did I like it? Does it hurt? Should she try it? etc etc. We were going out tonight and were waiting for our friend Cushla to arrive before we all hit the town but seeing as at the moment it was just the two of us in her apartment I didn’t mind talking with her about my obsession, it was only when we were out in public and she started on the topic that I got embarrassed, mainly because she was just so loud.
“So, tell me about it Portia.” Sienna giggled “Why do you like it so much?”
We’d had this conversation so many times before but as usual I humored her.
“I guess it’s just something I’ve always done, pretty much since I started having sex.” I started recalling to Sienna the story of my first time. “Remember me telling you about Hamish? He was the one that got me into it. He was a bit rough with me and I didn’t like it at first but after a few times I started to enjoy it. Since then I’ve done it with other guys who have been a lot more caring and taken their time rather than just shoving it in and that’s what has really turned me onto it. If a guy knows what he’s doing it can be really great.”
Sienna had a funny smirk on her face.
“What is it?” I asked.
“I’m just picturing you bent over on the back seat of Hamish’s mini minor taking it up the arse.” she replied.
“Shut up!” I teased, slapping her arm.
There was a slight pause, almost as though Sienna wanted to ask me something else but was too scared. I broke the silence. “So, you still haven’t done it?”
Sienna shook her head, “No, but I think I’d like to. It would have to be with the right person though you know? I don’t want to do it with someone I don’t trust.”
I nodded. There was another awkward pause. This time it was broken by Sienna.
“Maybe you could show me how to do it?” she suddenly blurted out.
I nearly dropped my drink. It was something we had joked about before when we were trashed but this time she almost sounded sincere.
“I mean, I trust you more than I do any guy I know and since you’ve done it so much I’m sure you would be the best person to show me how.”
I’d never done anything with another girl before, apart from a drunken snog, I was purely a guy only girl but I could imagine doing something with Sienna, she was quite beautiful afterall, not some butchy bull dyke, the guys certainly liked her. If I was going to be involved in any girl on girl activities it wouldn’t be hard imagining doing it with her.
I decided to call her bluff, to see if this was just another one of her games.
“Ok,” I said, turning to face her “We’ll do it. It will be like coaching or something.”
“Alright,” Sienna clapped her hands “Ooh I’m quite nervous but excited.”
The downstairs buzzer rang.
“That will be Cushla.” I said
“What should we say to her?” asked Sienna pressing the door access button “I don’t want to go out now, I want to do this.”
She sounded like a spoilt child that had had her favourite toy taken away.
“Wait!” She had suddenly hit upon an idea “We’ll ask her to train with us.”
“I don’t know Si, do you think she’ll be into it?” I asked worriedly.
“Only one way to find out.” replied Sienna bouncing up and down in excitement.
I was quite surprised to see her so enthusiastic about the whole idea.
There was a knock at the door and Sienna answered, a huge smile beaming on her face.
“Someone’s excited.” said Cushla as she walked in, tossing her bag on the couch.
“We’re not going out anymore.” Sienna began. “We’re staying in and having fun instead.”
“What? Why?” whined Cushla. She’d obviously gone to a lot of trouble to make herself up for the night.
“Portia is going to coach us.” Sienna huffed, as though it was so obvious.
Cushla was excusably confused. “Coach us, what are you talking about?”
“Portia is going to show us how to take it up the arse.” Sienna explained matter of factually.
“Right,” Cushla answered sarcastically. “Look, whatever you two want to do that’s fine, just count me out Ok?”
She got up to leave but Sienna grabbed her elbow.
“No, stay. It’s going to be fun. You can just sit and watch if you want, you don’t have to do anything.”
Cushla looked over at me suspiciously but I nodded back to her reassuringly and told to her to stay. She sat back down on the couch and didn’t say a word.
“Hang on, I’ll get some things” Sienna ran into her bedroom and returned with a couple of differently shaped and sized toys, a tube of KY jelly and some other paraphernalia and dumped them in Cushla’s lap.
“Yuk!” exclaimed Cushla throwing the toys onto the floor.
“Shut up Cush, like you’ve never seen a dildo before. Ok coach, how do we start?”
Sienna was really into the idea now, already stripping off her top and jeans. Standing in front of us in her underwear I looked her up and down. She really did have an amazing body and her long blonde hair flowed over her shoulders and across her breasts. Confusingly I felt my crotch suddenly get hot. That was weird, I liked guys right?
‘Ok,’ I thought to myself ‘here we go.’
“I guess the first thing to do is to get mentally prepared for it.” I started. “Taking something, anything whether its just a finger or some guys huge cock up your arse is quite different to taking something normally. It will probably feel a bit foreign at first and you might get the feeling that you want to push it out but you just have to relax and go with it.”
Sienna was looking at me intently, taking in everything I was saying like an over eager student. Cushla meanwhile was sitting on the couch trying not to pay attention.
“Relaxing is very important.” I continued. “You don’t want to let yourself get uptight about it. Just relax and don’t let your arse get all tightened up.”
“I’m relaxed, I’m relaxed, lets do it!” squealed Sienna, pealing off her panties and jumping about.
I turned to Cushla, “Cush, could you pass me that tube of lubricant?”
“Don’t ask me to do anything, I don’t want to be involved.” she replied.
I bent over myself, picked up the tube from the floor and I handed it to Sienna.
“The easiest way to reach is if you kneel on the floor and reach around behind you” I said.
“No, no, no,” Sienna said looking up “No, I want you to do it. I could have done it to myself anytime. You’re supposed to take me through it.”
“Ummm, Ok.” I replied. Now I was nervous. I’d never touched another girl in a sexual way and wasn’t sure how I would feel about it.
I knelt down beside Sienna, who was now on all fours and sticking her arse up in the air. I slowly reached out towards her and touched her thigh then gently ran my hand over her arse cheek. It was smooth and soft and felt like my own. Sienna giggled and took a sip of her wine.
“Aren’t you guys grossed out touching each other like that?” Came Cushla’s voice from behind us. Sienna glared at her, “Don’t ruin the fun.”
I continued to run my hands over Sienna’s lovely backside, getting her used to the feeling of hands concentrating on that area. I tried to imagine myself as a guy feeling up this hot girls arse but that made me feel kind of like a lesbian so I pushed that thought aside and instead concentrated on making my friends first venture into bum fun as comfortable as possible.
Sienna was obviously no stranger to the female touch. She was easily my most sexually experienced and adventurous friend and although she’d never told me about encounters with other girls it was obvious from her reactions to my hands on her that she was in no way uncomfortable with it. She moaned longingly as my hands wandered over her arse cheeks and pushed herself back against my touch. I positioned myself behind her and gently pulled her arse cheeks apart, getting my first glimpse of her tight virgin rosebud. It was the first time I’d ever really seen another girls arsehole in real life, me always being the recipient of arse play. It looked so incredibly small that I began to wonder if anything would be able to penetrate such a tight orifice.
“How do I look?” Sienna asked, peering at me upside down between her legs.
“It’s quite amazing,” I responded. “I’ve always wondered what it would be like on the other side.”
“Well then go for it.” came her response.
I gazed cautiously over at Cushla, who was looking at the two of us in either shock or amazement, I couldn’t tell, then returned my focus to Sienna’s asshole. Without another word between us Sienna reached back and with two hands separated and held apart her lily white buttocks, exposing herself to me completely. I slowly leaned forward, my face getting closer and closer to her bumhole. I could feel myself trembling. When my mouth was about an inch from her puckered ass I slowly stuck out my tongue. It seemed to take forever for me to reach her, then suddenly I felt the tip of my tongue come into contact with Sienna’s quivering tush. She let out a sharp sigh of relief at the touch, followed by a louder moan of pleasure as I ran my tongue over her tight hole.
“Oh fuck, that feels amazing.” Sienna groaned, pushing her arse back against my face. I pulled my head back and asked “You’ve never had anyone even lick your arsehole before?” before returning between her soft cheeks and resuming the rimming.
“No, never.” she answered. “Ohhh, god yeah. I didn’t realize it would feel like this, oohhh!”
I continued using my tongue on Sienna’s arse for several minutes before the desire to explore another girls body became to much and I had to know what it was like to lick her pussy. My mouth ventured a little further down until I came face to face with her sopping wet snatch. Without hesitation I buried my face in her, my tongue delving between her hot folds.
Sienna let me indulge myself for several minutes before reminding me of the true task at hand “While that feels incredible and all, I thought you were supposed to be teaching my arse.”
“Sorry,” I replied “I just had to know what it was like.”
“Yeah, I get it. Now if you would be so kind…”
I returned to my anal duties, lapping once again at Sienna’s virgin backdoor but now, between ever half dozen licks or so I began to gently push my tongue harder against her asshole. But it refused to let me in, remaining tighter than ever as I tried desperately to squeeze my tongue into her. Eventually I gave up, my tongue being just too soft to penetrate such a stubborn entrance.
I sat back up and shrugged my shoulders at Cushla who was now watching intently. She quickly realized how closely she’d been observing and sat back up muttering to herself. “Don’t know what you see in it. Arses or girls, no thanks.”
Ignoring her ramblings I reached for the tube of lubricant that lay on the floor beside Sienna’s leg. I lifted the tube to her bottom and squeezed out some of the liquid onto her asshole. “Oh shit that’s cold” Sienna giggled.
“It’s Ok, I’ll warm it up.” I said, gently rubbing the lube into her ass with my index and middle finger. Sienna soon resumed her moaning and sighing and I decided that it was time for her to experience her first anal penetration.
“Ok Si,” I said “I’m going to try to push my finger into you now. Are you ready?”
“Oh fuck yeah.” came the reply.
I applied some pressure and pushed my middle finger against her now slick asshole. The lubrication helped and my finger slide into her passage to the first knuckle. I worked the end of my finger into her slowly and gently made tiny circular motions as well, hoping to open her up a little. I pushed again and my finger sank into her ass to the second knuckle. Another tiny push and the digit was completely submerged in her rectum. I could feel her pulse throbbing around my finger, her sphincter gripping my finger tightly.
“My finger is completely in you Si,” I told her “Are you Ok? How does it feel?”
“I’m fine, it definitely feels different but good. I think I can handle another finger.”
“I’ll be the judge of that,” I said “lets not rush things.”
I began to work my finger slowly in and out of Sienna’s sweet arse, letting her adjust to the sensation, then started to make small spiral movements inside her, getting wider as my finger pulled our of her. Her asshole was starting to give in a little now and I could see that she was ready for the next finger but I let her relax a little more first, continuing to frig her before I began to push the next one in.
With the work I’d put in loosening her up my second finger was met with much less resistance and soon the two of them were sliding in and out of her hot arse. Her muscles still gripped my fingers hard but I could feel that they’d given up the fight to block me completely. I wondered if my own arsehole had been so stubborn in the beginning, was Sienna just exceptionally tight or was this the norm for virgin arses? I was now feeling a power I hadn’t experienced before. Being in control of my friend’s bottom was really turning me on, this must be what guys feel in this situation, God it was wonderful, she was totally at my mercy and…
“Ow fuck, that’s a bit rough.” I suddenly heard. Shit, while I was off in my fantasy world I must have been unintentionally fingering Sienna’s arse quite hard.
“I’m sorry, I got carried away.” I apologized.
“That’s ok, just remember I’m new to this.”
I slowed the pace back down until I saw Sienna loosen her grip on her buttocks and relax again. I continued to work my fingers into her and after a little while longer wiggled a third digit into her arse. I began to stretch my fingers out inside her bum forcing her tight opening to expand some more.
It was at this point that I noticed out of the corner of my eye that Cushla was watching us again. She seemed completely engrossed in the two of us, me grinding my fingers into Sienna’s bottom, Sienna moaning and gasping over the new sensations she was experiencing. I pretended to ignore her and continued to finger Sienna and also rubbing my own clit with my free hand.
I looked over at the two dildos Sienna had brought out of her room. The first was an average sized vibrating toy, long and white and about as thick as an average sized cock. The second was quite a bit larger. It was purple and modeled on a realistic dick look with ‘veins’ and a ‘circumcised head’. It was about eight inches long and wrist thick.
“Sienna, I think you’re ready to take your first ‘cock’” I said.
“Oh fuck yeah, give it to me bitch.” Sienna replied in a half mocking tone that made us both giggle.
I pulled my fingers from her arse and lubed up the smaller toy.
“Ok Si, I’m using the smaller dildo. When you feel me pressing it against your arse I want you to push out slightly, not too hard, just a little ok?”
“Yep, push it in.”
Sienna wanted it bad.
I brought the tip of the ‘cock’ up to her anus and pressed it gently against her. I saw her respond by pushing her puckered bunghole outward, at which point I pushed the toy into her harder and watched in wonder as its length sank into her bum.
As I slid the entire toy into her rectum in one push Sienna exhaled a long deep breath “Oooooohhhhh fuuuuckkkkk.”
“Ok Si?” I asked.
“Yeah, it just feels very different. Can you fuck me with it? I want to feel it in me.”
I began to thrust the dildo into her, watching as her arsehole gripped it like a fist almost making it hard to work into her, even with the lubrication.
“Oh my god,” Sienna responded “fucking hell, its so intense.” She pushed back against the plastic dick, burying the whole thing in her tight curvy bum and groaning hard.
I loved how much Sienna was enjoying her first anal experience, it was causing my own arse and pussy to twinge in excitement. I was almost jealous of her, wishing I could relive that first time feeling again. I remembered the mixed feelings of pleasure and pain I had felt those first times and it occurred to me that Sienna was really enjoying this too much. I had been taking it very easy on her up until now but no one had ever done that with me. I wondered how far she could be pushed and with that thought pulled the dildo from her arse with a pop.
“Enough of that,” I said “You’re taking this one far to easily. I think I’ve warmed you up too well. If you really want to have the full anal experience you need to discover the fulfillment that can come with mixing the pleasure with pain.”
“Ok, I think I can do it.” Sienna replied.
“We’ll see.” I said, greasing up the bigger toy.
All of a sudden Cushla spoke up. “There’s no way she can take that.” she said unexpectedly. Sienna looked around over her shoulder with a concerned look on her face.
“What makes you such an expert? Don’t listen to her,” I said “You can do it, it’s just going to take some will power and a little effort from you and me.”
Cushla was now leaning over us, trying to get a better look at the proceedings. I brought the well lubricated ‘head’ of the big toy up to Sienna’s arse and rubbed it in little circular motions over her hole. I held the shaft with one hand and pressed the palm of my other hand against the base and pushed gently. Sienna’s arsehole resisted the intrusion, refusing at first to let the giant rubber knob in. I turned to Cushla. “Put your hand on mine and help me push.”
Without hesitation Cushla put her hand over mine and added her strength to mine.
Sienna’s sweet rear end stood no chance now. As we watched her arsehole began to slowly expand, forced to stretch around the head of the ‘cock’ being pressed into her. As her ring was widened to new limits she began to whimper softly and then started to shake.
“Are you ok Si? Do you want me to stop.” I asked
There was a short silence before she answered, a little choked up. “No. I can do it.” she spluttered.
‘Good girl,’ I thought ‘such a positive student.’
Cushla and I applied more pressure to the base of the ‘cock’ and the head disappeared into Sienna’s bum, followed by a loud cry as she struggled to accept it.
“Let it out,” I told her “let it out and go with it, remember to breath. It will be worth it, I promise.”
Sienna didn’t answer, only buried her head into the carpet muffling her cries and pulled her arse cheeks further apart. I took this to mean she wanted more and so continued to force the toy into her.
When half the dildo was inside her arse Cushla and I laid off the pressure and let Sienna try to adjust to the rubber cock. He arsehole, stretched smooth around the purple shaft looked so fucking hot and I was so proud of my new pupil, taking on such a massive task on her first day.
“That’s hot.” said Cushla, as though reading my thoughts and looking down at the toy jutting out of Sienna’s bum.
“You’ve changed your tune.” I said.
“I didn’t realise it would be so sexy, it just looks so….hot.” she couldn’t think of a better adjective. And neither could I. I was always fascinated by the look of a girls arsehole being stretched to it’s limits, even though I was a lover of men. I just thought it was the sexiest thing to see.
Sienna had brought her head up from the ground now and was obviously learning to accommodate the ‘cock’. I took hold of the base and began thrusting it into her rear. Her head fell to the floor again and she began to groan in low almost unsettling way as I fucked her arse good and hard. I was loving being in charge, it was a completely new thrill but I needed more. I handed control of the dildo over to Cushla and stood up, picking up the rubber strap-on harness that Sienna had brought out with the other toys and slipped my legs through the leg holes, then did up the velcro tab at the back.
Cushla was getting overexcited by the whole thing now, pushing the toy too hard and too deep and causing Sienna to cry out for us to stop. I took the reins again and brought Sienna back under control then gently slid the rubber cock out of her. Her arsehole, now free of the large toy, gapped open at us. Cushla eye’s widened at the sight ‘Wow’ she exclaimed in total awe. I pushed the purple cock through the hole in the front of the strap on harness and looked down at myself, admiring the dildo as though it were my very own hard-on. I felt such power and authority and immediately had to try it out.
I crouched behind Sienna and brought ‘my cock’ back to her widened arsehole. “I’m going to fuck you now Si,” I said “I’m going to fuck you hard and I want you to take it.” I was quite surprised to hear words like that coming from my own mouth, it was like having a dick was bringing out the commanding male in me. Sienna didn’t answer, only pulled her cheeks wider apart and waited for me to push into her. She was well and truly loosened up now and I could easily push ‘my cock’ into her. I took her hips in my hands and thrust my own hips forward burying the tool deep into her arse in one push and forcing a high pitched moan from Sienna as she was once again stretched to limit by the cock. This time I gave her no time to adjust, placing my hands on hers and helping to pull her buttocks apart as I repeatedly drilled into her shitter. Each thrust I gave pushed her forward and produced a small cry from her lips, I couldn’t tell if she was loving it or wishing I would stop but as she hadn’t said anything I continued to hammer her arse, spearing the purple cock deep into her rectum.
I had been banging Sienna’s bottom silly for nearly five minutes before I noticed her starting to shake slightly. Then her little moans began to grow longer and her breathing more rapid and sharp. “Ooooooooooooh my god, oooooh fuck!” she began to cry. Her right hand let go of her bum cheek and began to furiously rub her clit as the first wave of ecstasy exploded inside her. Her screaming became so loud I knew the neighbours would hear. “Fuuuuuckkkkkkk!” she cried as her orgasm tore through her body, shaking her violently as though she was possessed.
Eventually she calmed down and I slowed my thrusts, gradually coming to a stop and drawing ‘my cock’ out of her. Sienna fell in a heap on the floor, little post orgasm vibrations occasionally shaking her body. She just lay there, her eyes glazed over, staring into space. I waited, slightly concerned that I had caused the crumpled heap on the floor some serious damage. Finally she caught her breath long enough to speak.
“That was the single most amazingly intense experience of my life,” she whispered. “I can’t even move.”
“You did pretty well for a first timer.” I said encouragingly “Think it’s something you’ll want to do again?”
“That’s all I want to do.” she answered, closing her eyes and reaching around to feel her arsehole. A worried look appeared on her face “Jesus, I hope it shrinks up again, you could drive a truck up there now.”
“You’ll be fine” I reassured her “You might be feeling it a bit tomorrow though.”
Suddenly there was a small commotion behind me. I turned around to see Cushla throwing her clothes off and pulling at her underwear.
“What are you doing?” I asked.
“You have to do me now, I can’t witness that without needing to know what its like too.” Cushla answered tearing her stockings off and pulling her panties to her ankles.
“Ok,” I said, I was amazed that she’d come around to the idea so quickly but I didn’t want to scare her off with more questioning.
“First I’ll need to loosen you up a little.” I said, bringing my hand up to her arse. Cushla pushed it away, dismissing my offer.
“Fuck that, just put it in me.” she demanded. “I want that fucking thing in my arse now!” She was obviously excited and although I didn’t want to hurt her my new sense of power suddenly got the better of me.
“Ok bitch,” I teased, bringing myself up behind her. I knew there was no way that Cush would be able to take ‘my cock’ without preparation. She was a strong willed girl but that wasn’t going to save her when her arsehole was being forced open by a wrist thick dildo.
I pressed the head up against her tight opening now, she still had time to change her mind.
“Are you ready bitch?” I asked her.
“Just give it to me!” she snapped back.
That was it. I trust my hips forward but came up against immense resistance from her bum. I grabbed her hips and pushed hard, forcing ‘my cock’ into her. I looked down to see her small orifice suddenly stretch wide and engulf the dildo, my pushing forcing the entire shaft into her bum in one single movement.
Cushla’s head flew back as she cried out but I wasn’t stopping now. She’d asked for it and now she was going to get it. As her long black hair flicked back I grabbed it in bunch and pulled her head back as I began to ram ‘my cock’ into her tight arse. Cushla gritted her teeth hard and her big eyes crunched shut, I knew she wanted me to stop but her stubbornness wouldn’t let her ask. She couldn’t let herself be beaten. Instead she held on, taking the huge toy up her virgin arse like a pro.
“Just breath around it.” I said to her “Let yourself go.” And she did.
“Fuck, fuck, fuck, aarrgghhhhhhhhhhh!” she screamed, her cries finally admitting to us that she was struggling.
“Relax Cush, just go with it.” I said, pulling her head back again and continuing to bang her behind. Her breaths become short and shallow followed by long whines as she endeavored to cope with the sensation of having her arse empaled for the first time.
I was feeling so empowered in my new role as the dominant partner that I forgot all concern for my new pupil, tearing into Cushla’s rectum with my fake cock. Then suddenly I felt something pushing at my own backdoor. Sienna was behind me, trying to work something into my tush. I relaxed my arse and felt the intruder slide into me. The thing felt slightly ribbed and was big, big enough to remind me to take it a little easier on Cush. It took me a few seconds to find a rhythm that aloud me to push ‘my cock’ into Cushla as the whatever it was that Sienna was forcing into my arse was on the out stroke. I soon had it down and found myself enveloped in yet another new feeling, the combination of taking it up the arse at the same time as forcing ‘myself’ into someone else was almost like watching myself being fucked.
I noticed now that Cushla’s desperate panting had cooled down a little and she now seemed to be taking to anal in quite a big way, pushing herself back hard against me and grunting in response to each thrust. Then the dirty talk started. Hearing such filth coming from her mouth as I deflowered her was such a turn on and in conjunction with coping it myself I began to feel my orgasm swelling up within me.
“Fuck me you bitch, fuck me harder,” Cushla bellowed in between her deep breathing “Oh god! Ram that rubber dick up my fucking shit hole!”
I couldn’t believe her dirty mouth, this was a girl that only an hour ago was disgusted at the very thought of taking anything up her precious exit let alone from another girl, but her words were definitely having an infectious effect on me as I found myself screaming out.
“Oh fuck Sienna, give it to me harder, I can take it, just fuck my arse you slut!” I screamed out over the top of Cushla’s cussing.
Whether Sienna was turned on too or insulted by my comments I couldn’t tell, she only responded by pushing whatever it was she was using deeper and faster into my eager arsehole.
It sent me over the edge. I suddenly felt myself drift off into the back of my mind then BANG, my orgasm exploded through me. I started fucking Cushla with wild abandon as I came harder than I can remember cumming in a long time, sandwiched between these two beautiful, newly initiated butt sluts, their soft skin rubbing against mine as wave after wave of pleasure washed over me. I collapsed on my side, pulling ‘my cock’ from Cushla’s dilated ring and feeling my own arse empty as Sienna pulled the thing out of my bum.
I turned over to see what it was.
“Corn on the cob anyone?” Sienna asked cheekily, holding up the yellow vegetable. Before I could respond Cushla was already on it.
“Yes please, now!” she said, spreading her cheeks and pointing her bottom into the air again and displaying her newly christened arsehole to the world.
‘Fuck,’ I thought to myself, smiling, ‘I think I’ve created a monster.’