Rock Hard
Nikki Flynn
Cover Image By: Megan Brooke
Copyright 2009 by Nikki Flynn
Smashwords Edition
Teaching By Example
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 favorite 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.'
Parking in the Rear
We had been lovers for at least six months. I loved his demanding passion, and he clearly loved my neediness. We usually fell into each others arms the moment he walked through the door, and most of the time we were screwing long before we made it to the bedroom. The sofa and chairs in the living room, the floor in every room, kitchen table, washing machine, shower, bathroom sink...we landed on whatever was closest.
He likes to fuck hard, and he has great stamina, so we go for hours sometimes. I love the way he pounds my pussy until it hurts. I love that every time I move for the next few days, I still feel him between my legs. We usually go through two or three positions in the location where we land before we come. Afterwards, we wander into the bedroom and lay wrapped in each others arms, and usually end up fucking again before falling asleep.
I absolutely love sucking cock, which he realized pretty quickly. If he put his cock anywhere near my lips, I was salivating. He was more than happy to stick his dick in my mouth almost every time we were together, and he loved to stare into my eyes while I sucked his prick and his balls.
He finger fucks me like no other man ever has, and while he doesn't do it every time, he does sometimes like to cum on my body, my face, and in my mouth. I love that, too. It is so incredibly erotic to watch him start to spurt and to feel his creamy, sticky load coat my skin or fill my mouth.
However, there was one thing that he wanted that I simply could not seem to manage. He wanted to (in his words) "fuck me in the booty." He put his finger in my tight asshole frequently, and while it did hurt at first, he knew exactly how to distract me by tweaking my nipples or slamming his dick into my cunt really hard and deep. I loved the idea of him filling my ass and pussy at the same time, and I soon learned to love feeling his finger inside me that way.
He tried repeatedly to stick his dick in the same way with little success. As much as I wanted to please him, I was really afraid. He tried to be gentle. He lubricated himself well and placed the tip of his cock against my asshole, and worked it gently, stretching me a little at a time. He tried to be a more assertive, lubing it and telling me to relax while he tried to just push his way in. That might have worked if he had been less considerate, but he wanted me to like it, and each time he tried it like that, I panicked. He bent me over the bed and when that did not work out, over a chair. He laid me down and put my legs in the air, and when that was unsuccessful, put me on my hands and knees doggy style. He tried to make me feel more in control of the situation by sitting down and having me sit on his dick as if I were sitting in his lap. Pain again, and panic.
He was wonderful through all the attempts, patient and gentle and reassuring. He insisted that I just needed to relax to enjoy it. I tried to relax, but as most people realize, when you "try" to relax, you do not. I was frustrated and annoyed with myself. I wanted to do this because it was clearly important to him. However, I am a wimp when it comes to pain, so the whole situation seemed to be a catch twenty two.
Most nights, he sleeps on his back, and he always pulls me over to lay my head on his chest, then wraps his arm around me, and we usually stay positioned that way. We usually wake up sometime during the night, entangled, and fuck again before falling back asleep. Then, in the morning, when we wake up wrapped around each other again, by the time we stretch and move around a little, he is hard again and I'm all wet, so we end up fucking one more time to start a new day.
One night, after another failed attempt at the booty, I woke up entangled with him as usual, but this time, we were laying on our left sides spooned together sensuously. I started to adjust myself a little to get more comfortable, and as is his habit, although asleep, when he felt me move, he immediately tightened his arms around me and pulled me closer. He likes having me tight against his body, and I love when he holds me that way because I feel confined and protected. Due to the sleep position being unusual for us, I was a little confused when I felt his dick against my ass. He was still mostly asleep, so although I could feel movement against my butt, as if he were slightly aroused, he was not fully erect. He was pressed into the crevice, and I could feel the length of him with the head an inch or so away from my pussy.
It felt pleasant, and I started to wriggle slightly, adjusting myself against him. His dick began to stiffen, and I started to kind of grind myself against him gently with a slow, steady rhythm. It felt sexy and sensual, but very relaxed, the feeling of his dick so close to my pussy, his body so close to mine, and his arms holding me so tightly. Neither of us was fully awake. We were groggy still, and content from the prior night's lovemaking.
I felt his cock stiffen as he matched my rhythm and pressed more tightly against me. He stroked me absentmindedly, softly and gently with his fingers. It was very erotic to me - the contrast of his gentle, endearing touch, so different from the demanding, rough pulls and grips of the night before. He slipped his fingers down to my pubic mound and continued his soft gentle strokes, no pressure at all, just light, feathery brushes across my skin.
I felt a twinge between my legs. Deep in my cunt, I felt the start of that familiar ache. I jutted my ass back against him, attempting to position my pussy against the head of his cock. He responded by pressing himself into me closer, and moving his fingers to my labia. He continued the soft feathery strokes around the folds of my pussy lips. He teased his way up and down, strumming and brushing his fingers against me slowly, never parting the lips, never moving to my clit, and it was deliciously maddening.
I could feel myself melting, liquid starting to flow from my yearning cunt. I pushed myself against him and tried to wiggle my pussy onto his now stiff dick. He remained still, letting his pulsing, hard cock rest between my ass cheeks, and moved his other hand to my swollen, puffy nipples. I have big tits, 38DD, and fat, rose-colored nipples that are extremely sensitive. I can come just from having my nipples touched, and he knows exactly how to turn me into a writhing, begging little slut by playing with them.
He moved both hands to my tits and began brushing the palms of his hands, then his fingertips, across my nipple tips. As I began to grind my ass against his cock, he took my nipples between his thumbs and forefingers and began rolling them gently. As I started to squirm even more, he began to pull and tug on them softly, allowing them to pop loose and kind of bounce free every few minutes. He alternated the plucking and pulling with flicking his fingers against the sides of each nipple rapidly but lightly.
The feelings that coursed through my body were exquisite, but the ache in my cunt had become an intense craving, and as the muscles inside tightened and squeezed involuntarily, the churning sensation made me squirm. His cock had hardened and I could feel it against me stiff and pulsing. I wanted to feel it inside me instead, plunging and filling me full. I arched my back, and reached my arms back over my head to wrap my hands around his neck. He nuzzled against me, breathing into my ear, alternately blowing lightly and running just the tip of his tongue around the orifice.
He also had started to alternate the gentle flicks against my nipples with periodic pinches, jarring my senses and making me moan. I pushed my body against him desperately, needing to feel him in me. He spread my pussy lips with his fingers and dipped just the tips of his fingers into the edge of my twat. He pressed there, just inside the edge of the opening, teasing in and out from the swollen, wet inner walls to the puffy, outer lips, wiggling his fingers just enough for me to feel the motion.
My body was on fire and aching for cock. I needed to feel his thick hard dick in me. I wanted him, and he knew he was making me crazy. As I moved against him, he continued to toy with my body, flicking and brushing my nipples, circling just inside my pussy with his fingertips only and licking and kissing my neck and shoulders. He started to press his cock against me, and I responded by grinding my body against him.
He worked his cock against the lips of my pussy from the rear, dipping slightly into my wet, dripping cunt, then suddenly plunged his fingers into it from the front instead. I didn't care how he did it, I was just grateful to feel something filling the emptiness between my legs. Just as quickly as he had pushed his fingers deep, he pulled them back out and began to play them around my clit. I felt like screaming in frustration.
However, he began dipping the head of his cock into my wet pussy and then sliding it back to my ass. It made my body quiver. I pressed against him, wanting his dick inside, needing to feel him in me. The head of dick was coated with the wetness from my pussy, and as my cream had oozed out, he had used his fingers and cock to smear the slippery natural lubricant around on my inner thighs and the crack of ass. He pressed his wet, throbbing dickhead against my tight asshole, and continued to stroke and rub softly against the lips of my pussy and my shaved pubic mound.
He did not increase the speed at all, even though he could feel me straining frantically against him. He continued to finger me slowly and gently, teasing my body mercilessly, and although I was aware of his cock pressing against my asshole, my attention was focused on the feelings flooding through my nipples, clit, and cunt. Even though the movements of his fingers were slight and measured, my erect nipples and distended clit throbbed and pulsed. He continued pressing his dick into my ass with the same slow steady rhythm.
I was beyond any thought other than fucking. I had become his little bitch in heat, wiggling, twisting, and writhing to get his dick inside. Position was irrelevant, I just needed cock. He inched his cock into my ass, pressing steadily but slowly and continued to finger softly around my clit. As he further penetrated my virgin ass, I stiffened as I became aware of the pain as his thick dick stretched me open. He immediately thrust his fingers into my creamy cunt and continued pushing his stiff meat further into my tight tunnel.
His fingers made me crazy. He knows that when I get really wet, I love the way he finger fucks me. He shoves three fingers in me deep and hard and thrusts and plunges in a way that makes me feel almost like I'm being fucked with a cock. He held my pussy cupped in one hand, thumb pressed close to my clit, fingers digging relentlessly into my dripping wet cunt. The muscles in my pussy squeezed and contracted with pleasure as he shoved his fingers in and spread them slightly, then withdrew to the tips only to ram them in deep again.
As he fucked my sopping wet twat with his fingers, he continued to work his rigid cock into my asshole. I felt the intrusion, but his fingers, which he was now alternately using to thrust into my wet, gaping cunt and brush and pluck my fat swollen nipples, had me so excited and stimulated that it was simply a subconscious awareness somewhere in my mind.
The distraction worked exactly as he intended, focusing all my energy to that burning ache between my legs deep in my pussy. I gyrated and pumped my throbbing hot box against his fingers frantically and purposefully, completely relaxing my ass and offering no resistance as he pushed his dick in completely.
Suddenly, I realized that he had buried his cock to the hilt in my ass. He had played with my tight puckered asshole with the head of his dick which was wet and slippery from the cream oozing from my cunt. He had teased me that way creating a pleasant, interesting sensation that was new to me. And as he stimulated my tits and twat to the point that I was excited almost to delirium, he had slipped his thick dick all the way into my virgin asshole. I was amazed, pleased, confused, and enthralled all at the same time.
Thoughts and sensations flooded through my mind. I concentrated on how his cock felt deep inside where no other man had ever touched me. I loved the fullness and the depth. He was still inside me, so I could feel his cock throbbing, and I loved the thickness and stiffness of him. My ass was tight and snug around his meat, slightly uncomfortable, I remember thinking, but the idea of him inside me that way distracted me from the minor discomfort.
He remained motionless for several minutes, allowing my body to adjust, and I suppose, savoring his conquest. I felt stuffed, his cock was thick and pulsing, and he continued churning his fingers slowly in my wet cunt and gently brushing his fingers across the tips of my nipples. Every nerve ending in my body seemed to be alive, with every stroke of his fingers, I felt jolts. I was keenly aware of the connectivity of my body parts because it seemed like a continual flood of electrical currents coursed from one nerve to the next with every touch.
I liked the feeling of him being in my ass and my cunt at the same time, and as I turned to look at him, he thrust his tongue into my mouth probing, then sucking. I felt like I could simply melt away in ecstasy. He began to move his cock very slowly, kind of grinding into me, but not backing out at all, and increased the speed and motion of his fingers in my pussy and on my nipples.
As he intensified the stimulation between my legs and on my tits, he began to pull his cock back slightly, and made gentle, short thrusts into my ass. It felt unlike anything I had ever experienced, his body seemed melded to mine. He began to work his fingers on my pussy and tits again, and moved his tongue from my mouth to my neck, one minute fucking my mouth with it, the next licking the hollow of my neck with rapid flicks. He then began sucking the same spot until I felt a twinge of pain, and quickly moved to suck my tongue as I tried to draw away from his.
He knows my body well, and he teased and plucked my nipples and began to ram his fingers into my wet pussy, pushing me toward release. My body responded just as he knew it would, sensations raging, cunt aching, and I moaned and pummeled my cunt against his fingers wildly. As I tried to ride his fingers, my ass swivelled and gyrated on his thick fat dick.
He knew I was flooded with desire, desperate to cum, and in that ridiculous place of need that encompasses all else. Nothing mattered to me except that insane insatiability. I wanted him slamming into me, ramming me full, forcing my body to respond. He pulled his fingers out of my quivering pussy and grabbed my nipples and held them between his thumbs and forefingers as he began to fuck my newly penetrated ass.
I felt the length of his cock slide about half way out, and then felt him push back to the place he had been. It was not painful, but it was not comfortable either. It felt intrusive. He pulled my nipples as if he were milking my tits and pulled his dick about three quarters of the way out at the same time. I moaned as he continued milking my fat nipples, and felt him shove his cock back to the original place deep inside, then start to pump in and out of my ass.
It did not hurt really, but I was conscious of being full in a way I never had been, and the sensation was very different from his cock in my cunt. I felt my insides tugging against his meat, and as he pulled out, it felt his dick was scraping the walls of my asshole. I guess he knew that my ass was tight, and that it would be somewhat painful, because when he pulled the length of his cock almost all the way out again, he shoved his fingers right back into my empty, wet, aching cunt.
He then moved them to the spot close to my clit that he knows will make me cum every time, and began to work on me. As I became hot and frantic again, he began to fuck me in the ass. He pulled almost all the way out, then shoved his pole back in deeply. He had my nipples and my cunt on fire again, and although I was aware of pain as he started to give me my first fuck in the ass, I was again beyond caring because it was minor compared to the pleasure also coursing through my body.
He pumped in and out slowly and gently at first, periodically grinding and sort of rocking his cock, I guess to loosen and stretch my muscles some. As my body adjusted, he began to increase his speed and movement. He pulled most of the way out, then plunged back in a few times, then settled into a rhythmic, steady stroke. This was the moment when I really knew and accepted that not only had he put his dick all the way up my ass, he was really, actually fucking me in the ass. I could feel my asshole tugging against his pole with every beat.
He was clearly enjoying the tight grip and pull on his hard, swollen rod, because he increased his tempo again. As he masturbated me toward climax, he fucked my ass deep and hard. He seemed to want to make sure that my first time taking it up the ass was one I would never forget, because he kept changing from one type stroke to another. He fucked with short, quick jabs, deep, long penetrating strokes, grinding gyrations and rapid, hard pumps.
As he felt me close to cumming, he began to hammer his cock into my ass the same way he pounds my pussy. He withdrew his dick to the head and the plunged it back in deeply in rapid fire motion, fucking my ass with the same demand I have felt in my pussy so often. Shockwaves of pain from the unexpected assault on my senses fought with waves of ecstasy exploding in my body while I came all over the fingers he had thrust back into my cunt.
As my body spasmed with pleasure, he rammed his thick heavy cock into my asshole with complete abandon - rutting...slamming his meat harder and harder into my tight ass. Maybe he wanted to make sure he broke my virgin ass in completely, maybe he wanted to make sure I understood how it could feel when he pounded me instead of making love to me gently. Whatever the case, I realized that his timing was perfect and intentional. I guess that he knew that while I was cumming, the elation would distract me. Within seconds after I came, he exploded, letting his load fill my ass. In addition to the strange sensation of his jism flooding my ass, I felt a sudden, intense burning sensation from the salty cream. My ass was raw and sore, but I had not realized until it until that moment.
He pulled out quicky, leaving me empty and sore but satiated. We wrapped around each other again, and he held me close and tight, basking in that feeling of complete satisfaction and oblivion that comes after really great sex. The first time I took it up the ass may not be my last.
My Neighbor
I didn't know her first name. She had been Mrs. Zimmer to me for all of my 19 years, well, for most of them. I probably wasn't even conscious of her until I was maybe 9, when I started my paper route. She lived with her husband three doors down. They had a daughter who was 2 or 3 years older then me. I didn't really know her, she was just there a few times when I went around to collect.
Funny how you form impressions of people from just brief encounters. I always thought of Mrs. Zimmer as a particularly sad woman. I also thought of her as smart and aloof. To me, she seemed like someone who knew a lot, didn't care to share what she knew and was somehow disappointed with her life and with those who entered it, me included. As a kid, I was always glad to collect my money and get out of there; she wasn't someone I enjoyed being around.
Perhaps that's why I was feeling a little awkward. Even though I hadn't thrown a paper on her lawn in five years, she recognized me and said ‘hello'. After I responded with the same word we seemed to have exhausted all potential for conversation and we both turned away. Maybe our cheerlessness was understandable: we were both waiting to get our teeth drilled.
It surprised me. Surprised me a lot. You don't expect to be thinking of a 45 year old woman when a guy in a mask is boring into your tooth. But I was thinking of her, her look of sadness more then anything. She seemed to be almost consumed by melancholy, lost in it, now, just like I remembered her during my paper route days. I don't know why but as I sat there gagging on a rubber dike I wanted nothing more then to cheer her up, to make her laugh, to bring a little joy to her eyes, a smile to her lips.
I got my chance about an hour later. She saw me walking along the street, stopped her car and asked if I'd like a ride home. Actually, it came out more like "Would you wike a wide home," and when I responded, with deliberate exaggeration, "I would wove a wide home," she burst out laughing so when I settle into the seat next to her I felt our shared laugh and dental experience had somehow brought us together.
It wasn't a long ride home but it was time enough for me to learn that her daughter was in 3rd year and thinking about going into law, following Mr. Zimmer's profession, and that Mrs. Zimmer owned a florist shop, or maybe even a number of them, I didn't quite get that straight. I wanted to get more out of her but she soon turned the turret on me and had me babbling about my future, as if I had any plans, as if I had the slightest idea how my future would unfold. When we turned onto our street I thanked her politely for the ride and, I don't know why, perhaps because I meant it, but I added that I really enjoyed talking to her. I told her she made me feel really at ease. That's when I heard her mutter, "That's a first."
It happens, doesn't it? You haven't seen someone in years and then you run into them twice in a matter of days. My second time with Mrs. Zimmer was in a coffee shop in the mall just three days later. I was sitting on a stool at one of those narrow, sweeping counters, looking at the wall when the person to my right got up and there she was, one stool away. "Hello again," she said and I said, because I had been thinking of it for two days now, "May I ask you a question?"
She turned a little on her stool to face me, "Of course." I could tell she was curious.
"Why did you say to me the other day, ‘That's a first." I could see that she didn't understand so I clarified. "I thanked you for the ride home and said that you really put me at ease in the car. That's when you said, ‘That's a first.' What did you mean?"
She laughed mirthlessly, "I've never been accused of making anyone feel comfortable."
I fell silent with this, I didn't really know what to say. And she was silent, too, she even turned away, but in a minute she turned back. "It was sweet of you to ask me about that. Thank you."