In For A Penny

Maybe I should start by saying that writing this sort of stuff doesn't come easy to me. Just making a contribution to an erotic site is not the Sam I've known/been all my life.

I've had a quiet time, really. Dull childhood. A little repressed, maybe. Never, for some reason, quite as fussed about dating boys as most of my classmates. I had offers, sure, but I wasn't bothered, that was the thing. Tho' I should make it clear that doesn't mean that I ever, once, thought about girls. Sure, there are all the tales above and below this one about sleepovers turned into orgies, and endless shower room fantasies. Well, not for me. Not once, ever.

When I was sixteen I started dating Bradley, and after about six months we had sex, the earth didn't move but no-one told me it should. And in due course we got married but haven't had kids because Brad doesn't want them. Yet. That yet has lasted eight years so far, and I'm kind of giving up hope. Of course I could miss a pill, but that isn't the Sam I know either. I guess I've given you enough of a picture of my marriage.

Through thick and thin my best friend has been Cassie. We started as roommates at college, and pretty much since then I've loved her very dearly. As a friend.

We're very different, which I think makes a lot of strong friendships. Funnily enough, we look different, as well as being it. I'm tall, slim, dark hair, and quiet. Cassie is shorter, quite a full figure, with beautiful straw blonde hair. (And the fact I've always thought her hair was beautiful doesn't mean I've always had the hots for her. It means I've always liked her hair. Get used to it). She's also got the kind of personality people call "bubbly". That means fun, not irritating. Because she's blonde and fun Cassie gets lots of attention from men. Not that she ever seems to want to settle down with one. About six months seems to be her limit.

Recently, Cassie seemed to have more time on her hands, and we found ourselves doing more and more together. It started off with going out drinking, but then Cassie went on a health kick. Insisted we start doing more sport together. At first it was tennis, but then when fall closed in we moved onto aerobics. Hell that was tiring.

So now you get your first shower room scene. Only thing is, it's the wrong way round. That is, I was getting undressed after aerobics, my clothes literally clinging to me with sweat. I'd turned away from Cass to take off my panties, because that's what modest girls are brought up to do. As I was bending over, I looked in a mirror to my left, and I could see Cassie staring at my ass. Well that's what it looked like.

My immediate reaction was it didn't feel entirely right, but then I rationalized it and thought she was probably lost in her own thoughts looking in the wrong direction. I forgot about it until the next week, then as my panties were coming off it occurred to me to check in the mirror again. Once more, it seemed Cass was taking in the curves of my butt. (I like my butt. I've said I'm slim, but it's nicely pert. Some thin girls have a boy's ass, but mine's definitely a lady's).

I felt a little uncomfortable with this attention, but still didn't make much of it. Women do, after all, admire other women's bodies, without there being a sexual element to it. And Cassie was one of the most actively heterosexual people I knew.

There's no doubt Cass and I were closer than ever. (And Brad and I were further apart). Then she said a friend was lending her his beach house for a week, why didn't we both use it? I fancied a week of sun and sand, and of course Brad just said "alright". So two weeks later Cassie and I were enjoying the sun, sipping a daiquiri on the veranda.

I won't bore you with the first couple of days. We quickly decided that the best place for catching the rays was on the veranda. Nice and private, with no men to hassle us. (Cass had stated on the way down this was a male-free week. That suited me).

Every now and then I still got the feeling that Cass was looking at me, but I put it down to me feeling frustrated. It had been a long time since I'd done it with Brad, and that hadn't exactly been satisfying.

By day three, I'd managed to burn part of my back, and I was going to cover up because I couldn't get the tanning lotion on properly, but Cass insisted that she could "protect me", as she put it. So off came my t-shirt, and I lay flat on my front in a simple blue string bikini. Cass knelt beside me. I could just about feel her knees brushing against the side of my left thigh.

Without saying a word, she reached across and pulled the string on my bikini top. I was quite startled, as she could easily have reached around the back strap. Then again, it was what people did when they sunbathed. Just not me, that was all. I felt the sides of my breasts slightly exposed, then figured that the only person who could see me was Cass, and she'd seen a lot more than that on many an occasion.

I was looking away, so the first thing I felt was Cassie's hands on my back, all slippery from the lotion. She started rubbing the lotion in, her fingertips pressing gently into my flesh. It felt beautifully relaxing, and, I have to say, totally non-sexual. It was a job that could have taken thirty seconds, but Cassie took a lot longer. I didn't mind, as she was effectively giving me a very relaxing massage.

I stopped feeling relaxed when her fingers slid inside the elastic at the top of my bikini pants. That didn't feel right. I sat up a bit and cried out "Cass!". She immediately removed the offending fingers, and apologized. "I was miles away," she said. "I never knew it could be so nice giving a massage." I didn't mention she was meant to be rubbing in tanning lotion.

We got steaming drunk that night, and the conversation turned to men, and sex. Cassie had always refused to believe that Brad was the only man I'd ever had, although she was ready enough to accept that we only ever had sex in the missionary position, and that he'd never gone down on me once. Cassie, on the other hand, seemed to have encountered all sorts of perverts in her life, our favorite being Ass Sucker, as we called him. He used to insist that Cass squat over him, and she had to wank him off while he licked her asshole. I found the idea disgusting, but Cass thought he was quite funny.

There was only one bedroom, with twin beds. Like I say, we were pretty drunk, and when we were in bed with the lights out the conversation carried on in the same vein. Cassie wanted to know my favorite sex acts. I didn't have many so I was treated to a long list of sordid things my best friend had done. Cassie sucking two men off at the same time, Cassie giving a blow job in a church, Cassie on all fours with a cock pounding her cunt and a finger roughly exploring her ass. Cassie described them all quite vividly. My main reaction was distaste, but I could also feel a light trickle between my legs. Cassie was a beautiful woman, as I'd had ample chance to see those past few days, and the image of her being used and abused in those ways was inescapably horny.

It seemed to have had the same effect on Cassie, because a minute or two after we stopped talking I heard the rustle of her sheet and a slight grunt. Realizing she'd given herself away, Cass said "I'm sorry, Sam, all that drink and talk has got me going. Do you mind?"

In all the time we'd known each other, even when we'd shared a room at college, I'd never "caught" Cassie masturbating. The idea of her lying only feet away, her legs slightly splayed as her fingers worked on her cunt, had my pulse racing even more quickly than all the things we'd talked about. After all, they were images, this was reality, even if it was a reality I couldn't see in the darkness of the room.

"No," I replied, nearly adding "go ahead" before I realized how ridiculous it would sound. In fact I did mind a bit, because I wasn't comfortable with the idea of Cassie frigging next to me. But I couldn't say that.

I heard her sheets rustle again as her fingers returned to her cunt. "You could do it too," she whispered. "It might be kind of fun." In fact my hand had, unconsciously, been moving towards my panties (I always wear panties and a t-shirt in bed), but her suggestion made me realize we were almost heading into troubled territory. I moved my hand back up, despite the need between my legs. "No. Thank you," I said, sounding ridiculous in my attempt to keep things normal.

The next few minutes were, as the saying goes, sweet torture. Cassie's sheets continued to rustle, and she emitted the occasional grunt. I felt very awkward, but at the same time the knowledge that such a beautiful person was touching their sex like that felt electric. It didn't take long before the rustling quickened, and Cass moaned softly. My lovely dear friend had masturbated to an orgasm next to me.

Minutes later I heard the soft sound of her sleeping. I didn't dare do what I needed to, and I barely slept at all that night.

Everything was a little strained to start off with the next day, but Cassie acted as if nothing strange had happened, and I decided to play along with her. In fact I wasn't quite sure what, if anything, had happened. Maybe what she'd done was just what friends do.

We were both feeling a little hung over from the drink, and at lunch time Cassie suggested some more cocktails as hair of the dog. I wasn't sure, but as always she talked me into it. By half way through the afternoon we were relaxed in the way only alcohol can make you. We were, once again, sunbathing on the veranda, laying on our backs in total privacy.

"Did you mind about last night?" Cass suddenly asked.

"What? Oh no," I lied.

"I got carried away. It felt so good Sam. I wish you'd...you know." I knew. But I didn't know how to answer. "There wouldn't be anything by it, would there?" she continued. "It would just be a bit more horny. It was even a turn on knowing you were listening. Do you mind?" I still couldn't reply. "Were you turned on? I would have been. I don't know what's happening to me Sam. I'm turned on now. Are you? Do you mind?" She turned her head round to look at me. There was an extraordinary intensity in her eyes. "Do you mind Sam?"

There were all sorts of things I could have said, about it being wrong, or disgusting, or more accurately that the idea I could actually see her do what I could only hear last night made me ache with a passion I don't think I'd ever felt before. But all I could do was shake my head - go ahead, Cass, masturbate in front of me.

She slipped her right hand inside her bikini bottoms. It wasn't exactly a full view, far from it, but I'm sure the shuffle of her fingers inside the fabric was more erotic than a hundred blue movies. "Go on Sam," Cass whispered, "you too. Let's do it together. Please, I so want you to."

I realized then that I wanted to, too. It was wrong, it was disgusting, it was almost lesbian, but the throb between my legs felt like an electric current. I started to move my left hand down to my panties. Cass looked at me, her right hand still frigging her pussy. "It'll be so good, Sam," she said, "it'll be so good."

I slipped my hand inside the waistband. I've never felt so purely sexual. Cassie's eyes were fully upon me now, her fingers barely moving inside the crotch of her bikini. "You look good, Sam, you look so beautiful. You are beautiful Sam."

The crotch of my panties was sodden. The touch of my fingers on my clit almost made me start. I'd never been so ready for an orgasm. Inadvertently I arched my back, thrusting my breasts up, displaying myself wantonly to my friend.

"Let me help you Sam," whispered Cass. She edged across the towels. Yes, I wanted her to see my breasts. I reached behind my back and struggled with the string. Then Cassie's fingers joined me, and in a second my top was off. My friend had helped to undress me. My breasts were proud now, the nipples poking defiantly up.

Of course I should have expected it, but for some reason it came as a surprise when Cassie moved further over and took one of my nipples into her mouth. Before it had just about been a game, but now Cass was making love to me. The thrills running through my tits meant I was never going to stop her. Her mouth felt so soft, as she nursed at both my nipples. It seemed to last for ages, as she took first one, then the other, swollen teat into the cool wetness of her mouth.

That would have been enough for me, but then her face started to move down my stomach.

"Cass..." I started to say.

"Sam, I want to, I so want to," she said. She reached my panties, and I wondered, briefly, what the hell was going on. What was I doing? But it felt too good, and as she tugged my panties down I lifted my ass to help her.

She rested her hands on my knees, and gently spread them, exposing me in a way I'd never been exposed before. She ran her fingers down the inside of my thighs. I watched her blonde hair disappearing between my legs. I could feel her breath on my exposed sex, then she was kissing my thighs, showing me a tenderness I'd never known with Brad.

Then I felt it. Beyond words really, but it was like the collision of the two softest rarest lilies as Cassie's tongue flicked languorously across my clit. I almost came then, and I think Cass realized how near I was, because she drew back, and pushed my knees up to my tits. I didn't realize what she was doing until I felt her tongue circling around my asshole. I was shocked - despite our conversation it wasn't something I'd ever thought about doing. "Cass, no!" I said, but then her tongue poked against my ass. 'What must it taste like?' I thought, but it felt good to me.

It felt extraordinary, spread-eagled with my knees to my chest and Cass slurping away at my asshole. Eventually she slid her tongue up to my clit, and then I felt another unexpected sensation, as Cass slid one of her fingers into my ass. It was uncomfortable but delicious, and I unconsciously bucked my body to force her penetration further.

It was all too much, and I felt a welling of emotion and passion. I fought for breath, and then rocked violently as I orgasmed hard against Cass's mouth.

I tried to recover, and was dimly aware of Cass delicately removing her finger from my butt. I lay there for a minute or too, dazed by how quickly things had changed. Cass just lay there, calm, peaceful.

It suddenly occurred to me she hadn't had her orgasm. God, how must she be feeling? I felt sure I couldn't do what she'd done. Then I looked at Cassie again. There was no demanding there, no insistence that she be given satisfaction. There was simple pleasure from what she had done with me. It was pure generosity. In that moment I felt a greater love than I had ever felt before.

I wanted Cassie to know how much she meant, how I realized what her love was. I grabbed her hand, and slid the finger that had been up my ass into my mouth. It was as intimate as I could be. Cass looked startled, but the look in her eyes revealed she was struck by the eroticism of my act. I knew then that a different set of rules applied with Cassie.

I wanted to enjoy her beautiful breasts, but there would be plenty of time for that. Right now my lover hadn't come yet. I leant over her groin, and tugged her bikini bottoms down. I was almost overwhelmed by her powerful rich musk. Her soft blonde pubic hair was matted with her honey.

I'd intended to use my fingers, but I suddenly felt that Cass deserved better than that. If I was going to make love to her, I was going to make love to her properly. I pushed her knees up to her bikini top, revealing her dark little asshole. I looked at it in wonder, lovely Cassie's most hidden secret. It was a surprisingly erotic sight, a dark little crater nestling in the creamy white valley between her butt cheeks. As I took the view in, summoning up the courage to pleasure my lover properly, I noticed a sprinkling of wispy blonde hairs surrounding the dark lines that disappeared into Cass's anus.

I moved my head down. I wasn't sure if there would be a smell, or a taste, but I heard Cass mutter "Oh Sam, yes", and I pressed my tongue hard against the firm muscle of her asshole. She moaned so loudly, I reached my finger up to her clit, and on that simple delicate pressure she groaned, her butt pressing against my face as she shook with her orgasm. It was an extraordinary feeling, almost being smothered by the flesh of my friend's ass.

When Cass had finished shaking, I pulled my face away and rested back. I was ready for more myself now, but wanted to give it time. After a minute or so, Cassie leant towards me, resting her chin on her left hand. I looked at her face, and I saw it in a way I'd never seen before. Beautiful, and lovely too.

Cassie leant further over. We'd made love, but we hadn't even kissed yet. Her lips were full and pink. Lips that only minutes before had been pressed against my ass. As mine had been pressed against hers. The idea of kissing after such private contact seemed deliciously dirty, and intimate. I moved forward quickly, and pressed my mouth against Cassie's. So soft, it made me wonder women had ever liked the roughness of a man's face. How could I have missed out so long? The kiss was deep and passionate. Two ass-suckers returning to home base. I explored her mouth with my tongue, almost leisurely, given the length of the time we kissed. There was no taste, or smell, but the knowledge itself was a potent elixir.

Eventually we parted, and looked at each other in a way I'd never shared with another human being. I knew this was something that would continue after we'd returned home, but for the moment I just felt relief and excitement we still had plenty of holiday left to go...