Problems

I am more than a little bit phobic about sex. I blame it on my Catholic upbringing. I’ve never had sex without throwing up afterward. I’m scared of getting pregnant; terrified of catching a disease; but mostly just creeped out by the idea of another person touching my privates. It really makes my skin crawl.

I don’t want you to get the impression that I’m a prude. Throughout high school I masturbated all the time, raiding my brothers under-the bed porn stash for inspiration. When I was 18, I bought my first vibrator.

Oh I lost my virginity, and it did little to increase my enthusiasm for the forbidden act. In my second year of college, I hooked up with a guy I thought was cute at a party. We were both a little drunk, and it was clumsy, awkward, uncomfortable, and over mercifully fast. At least I made sure he used a condom. The next month was torture. I got an AIDS test, I made a gynecologist appointment; I fretted and worried and counted the days till my period. The relief I felt when the test came back negative, and my period came on schedule didn’t encourage me to go out and have sex again.

For the next two years, I studied hard, and got good grades. I didn’t exactly have to fight off the guys; I am exceptionally tall, I don’t have big boobs, and I wear glasses. In the mean time, my pent up lust increased to the point of bursting. I remember masturbating in my dorm room, my ear pressed against the wall, listening to my neighbor fuck her boyfriend, tears running down my cheeks in frustration. My sex toy collection steadily increased.

In my senior year, I started dating Charlie. He wasn’t a ‘nice’ boy; he had a pierced tongue, and played in a band, and smoked pot, and most importantly, he didn’t pressure me to have sex with him. He was a hell of a kisser though, and eventually I worked up the nerve to ask him if he would like to watch me masturbate.

I liked watching him stroke himself with his eyes glued to my spread pussy, a slick purple vibrator sliding in and out. It was really only the second time I had seen a penis in real life. I liked the way his come shot out the end of it (safely away from me), and the noise he made when he came. It was really pornographic. My clit twitching, I had an amazing orgasm as he watched.

Needless to say, it quickly became a habit. I loved watching him get off, and he got off watching me. Overnight, I had an amazing sex life. One time he asked if I would use my hand on him, and to my surprise, I didn’t mind. I wore a latex glove, and pumped his penis until he cried aloud and his sperm splashed all over his sexy smooth chest. I liked how hard and smooth his penis felt, and how tight I could squeeze it. I like varying the rhythms, slower then faster until his balls contracted and the head turned bright purple. And I loved making him come.

So that’s the way it was. We’d watch porn together and masturbate; or he’d jack off while I toyed for him; or I’d put on a glove and lube up his stiff cock and give him a hand job. Life was good.

I could tell he was nervous. We were hanging out in my apartment, we had just had a couple beers, and this was the time of night when we would usually get naked and watch each other get off. He was being quiet, and I could tell something was on his mind. I was afraid that he was going to ruin everything and ask me to have sex with him. When he finally asked, I nearly laughed aloud. “Would I like to fuck him in the ass?” I’d love to! My cunt was dripping just thinking about it.

I let him pick out the toy. He chose one of my smaller dildos, a blue silicone one that looked like a mermaid. I was wet just thinking about it. He asked me to be gentle. “I’m a virgin at this”, he said.

He got on his hands and knees, his rump thrust obscenely into the air. His cock swayed rigidly between his legs, his balls were tight. A clear drop of precome leaking from the swollen purple tip of his cock got stuck to his belly and hung there in a shimmering arc like a sticky thread of spider web.

He looked back at me, eyes glazed over with lust. “Please fuck me, Andrea.”

I put on my latex gloves and started applying lube. He moaned and his little asshole winked as I dripped cool lube onto his anus. We were both incredibly excited.

I was gentle, and I took it slow, but he was so relaxed that it slipped right in. Before we knew it, the toy was buried to the hilt in my boyfriend’s tight ass.

“How does it feel?” I asked.

“It feels great” he whispered “now try fucking me.”

Gingerly at first, then harder and harder as he encouraged me, I started sliding the dildo in and out. I would withdraw it almost all the way out, then slide it back in. He would hump back against me, fucking back against my thrusts. I twisted the toy inside him, and he moaned satisfyingly. I was amazed at how wet I was, my juices were literally running down my thighs onto the sheets. I stopped holding back, and fucked him with a vengeance, ramming the dildo up his ass until my arm was sore and my shoulder ached. He was jerking off now, in time to my thrusts, and when he came, he arched his back and shouted, and the jet of semen hit him in the chin.

I couldn’t wait to get off. Leaving the blue cock inside him, I physically rolled him over and squatted over his face to give him a prime view. It took about two seconds of tugging on my clit before the orgasm started. I felt my toes curl and my pussy spasm, and I just let the waves roll over me again and again until I was done.

“That was amazing” I said, and he agreed.

“Let’s do that again.”

We did do it again. And again and again. Fucking his ass became a regular part of our sex life. I had no idea what I had done to make me so lucky.

Eventually it was over. He met another girl, one who liked normal sex, one who would touch his penis without needing to wear gloves. I don’t know if she fucks his ass, and I don’t ask. We stayed friends; we write Christmas cards and call each other on our birthdays. I guess that’s about the most one could ask.

After I graduated, I moved to New York. Do you have any idea how hard it is to date boys in New York when you aren’t really into the bar and club scene, and when you let the occasional guy who does ask you out know up front that you don’t put out? My love life was completely nonexistent.

After six months of frustration and jilling off to memories of fucking Charlie from behind, I decided that desperate times called for desperate measures. I placed an ad in the Village Voice.

“Tall, slim twenty something female seeks cute guy. I’m not a prude but I don’t like sex. Maybe we can have some fun together.”

I got a lot of responses. They were all from guys who were out to convince me that they were the one who was going to teach me to love sex. I didn’t get a single message that warranted a callback. Disgusted, I fell back on my two favorite indulgence; porn and dildos.

I knew my ad was still running, but I hadn’t bothered to check it in a week. There were six new voice messages, down to a trickle from the previous weeks. Five were the same old messages from the same old guys with the ‘wonder cocks’. One was from a girl.

It made me sit down and think. I’d never really thought much about lesbian sex. The idea of a tongue in my pussy ooked me out almost as much as the idea of having a penis in there, and it wouldn’t matter if the mouth belonged to a male or a female; it was still dirty. But I had seen a lot of lesbian porn, and I had nothing in principal against the idea of being with a woman. The message was brief, but her voice sounded nice. “My name is Laura, and I’m 25. I know you were looking for men, but I thought your ad was interesting, and I wondered if you would like to talk.” And she left a phone number.

I decided to give her a call: what the hell.

My heart was racing as I dialed the number. A combination of excitement and dread, I guess. The whole personal ad thing was stupid, humiliating. A girl answered the phone, and I almost hung up. No, it wasn’t Laura, it was her roommate. Could I hold on?

I held on, and Laura got on the line. We introduced ourselves, and there was an uncomfortable pause. I took a deep breath. “Listen” I said “there’s a couple of things I’d like to let you know right away. I’m not a lesbian. I mean I’ve never dated a girl before. But I’m not opposed to the idea and you sounded nice so…” my voice trailed off.

“Go on” she said.

“Well”, and I hesitated, not sure how to put it “I’m really not comfortable with physical sex. I’m not just talking about penises. I guess I have a bit of neurosis about it. I don’t like other people touching my… my vagina. But I do like to play.”

“How do you feel about touching other people?” she asked.

I laughed a little. “Well that’s a fair question. I guess I wouldn’t mind touching if I wore latex gloves. But I wouldn’t be able to go down on you” I was blushing furiously. “That’s probably not the sexiest thing you’ve ever heard.”

“It’s ok” she laughed “I have some hang-ups too. I think I’d like to meet you, if that’s what you would like.”

It turned out that we didn’t live far from each other. We agreed to meet at a bar a few blocks away.

It took me a long time to get dressed, and I’m not a fussy dresser. I was nervous and excited. I wanted her to be attracted to me. I wanted something to happen. What, I wasn’t really sure.

I spotted her right away. She was way cute. Everything about her was small: she was about five foot nothing and really skinny. Her hair was dyed bright red and done up in pony tails, she had freckles on her cheeks and flashing blue eyes, and she wore blue jeans and scuffed up Doc Martins. I loved her hands: she had little hands with clean, neatly trimmed nails. It looked like she worked with her hands and took good care of them. They were girl hands that were pretty but not pampered.

Right from the start we got along really well. Things only seemed awkward for a moment, and then we were chatting away like old school chums. We drank two beers together, and the topic of sex and relationships never came up. Then we were buzzed, and it was late, and we both had to work in the morning.

It was cold outside the bar. I took her hand in mine, and she squeezed back.

“Laura” I said “I had a good time tonight. Do you think you’d like to go out again?’

“Yeah” she said “I would.”

“Hey, would you like me to walk you home?” I cursed myself: what a dorky thing to say.

“No, you don’t have to do that. It’s totally out of your way. But if you don’t mind, I’d like a goodnight kiss.”

And so I kissed a girl. I was happy to discover that it wasn’t very different from kissing a boy, and at least as nice. I slipped my tongue into her mouth and held her tight. It seemed to last for a very long time. Then we both became conscious that we were in the middle of the sidewalk.

“Call me!” She waved and headed off. I was still reeling from the kiss. I hurried back to my apartment. My clit was throbbing, and I couldn’t wait to get home to my toy drawer.

The next day at work, I had an emergency conference with my friend Steve over lunch. “I’ve never been in a situation like this. How long do I wait before I call her?”

“Call her.” Steve said.

I called her when I got home from work. She wasn’t there, so I left a message. I then proceeded to mope around the apartment, pretending not to wait for her to call. A little after eight, the phone rang.

It was Laura, and she wanted to know if I would like to hang out. She suggested the bar we had met at the night before. I took a deep breath and mentioned that I had beer in my fridge. She said she’d be right over.

We had a beer, we kissed, we kissed some more, and then we moved onto the bed; kissing and touching and rolling around. Under my jeans, my panties were soaked. She reached up under my shirt, tweaking my erect nipple through my bra. I really didn’t want to fuck this up.

“Listen.” I said. “Stop for a second. I’m really excited, and I want to do things with you, but there are a lot of things I’m just not comfortable with.”

“It’s OK.” She said. “I’m not exactly… normal either.” There was a long silence, and we both looked at each other. “Would you be comfortable spanking me?”

“Spanking you?”

“Yes.” she said, and I realized I was holding my breath. “What I’d really like is for you to beat my ass, like really hard, while I masturbate.”

“I’d love to do that for you.” We got naked fast. I was drooling with lust for her taught little body. Her breasts were small and conical, pink nipples pierced with thick barbells. Her pussy had a soft triangle of dark hair over it: on her tummy just above the pubes, there was the tattoo of a butterfly. She bent over my bed, presenting her firm, pale butt for me. It was beautiful.

“Spank me” she whispered. I raised my arm and slapped her ass. Her flesh jiggled and I left the red imprint of my hand on her ass. “Harder. Don’t hold back.”

Her pussy was aroused, her labia pouting open and glistening with moisture. Her ass wiggled provocatively at me. I slapped her again and again, as hard as I could, turning her cheeks red, while she rubbed her clit.

I couldn’t keep it up long. It hurt my hand too much. “Don’t stop” she groaned, keeping a finger on her clit “use a ruler or a hairbrush or something.”

I got the hairbrush from my dresser. “Would you like to use a vibrator while I do this?”

“Fuck yes!”

I handed her one of my favorites. She slipped it right up her pussy and started fucking herself while her other hand kept busy with her clit, her face half buried in the sheets.

I beat her ass with the back of the hairbrush. I hit her as hard as I could. I started counting my strokes, but I lost track around twenty. She was gasping, sobbing, but always telling me not to stop.

Finally she gasped “I don’t think I can take any more.” I lowered my aching arm, and let the hairbrush fall. Her ass was a mess, all red and covered with angry raised welts. I had broken the skin in a couple places, and a trickle of blood ran down the back of one thigh. Her hands were busy between her legs, eyes shut and forehead knotted in concentration.

“Could I fuck your ass while you do that?”

“Please” she said “Do it.”

I grabbed another dildo from the drawer, and squirted lube all over it. It happened to be the blue mermaid that had been Charlie’s first choice. I was so excited I didn’t even bother putting on my gloves. I gently spread her poor abused cheeks, revealing the delicate brown rose of her asshole. I pressed the dildo inside her.

It was hard work getting it in. She was a small girl, and the resistance from the toy in her pussy made it harder. I took it slow and eventually I had the whole thing buried in her ass. I could feel the buzz and the frantic movement of the vibrator in her pussy, bumping against the dildo in her ass. I grabbed a fistful of her scarlet hair and pulled hard, twisting the dildo and fucking her ass mercilessly, and when she came, it was with a violence that almost scared me. She kicked and thrashed, her eyes squeezed tight and her face locked in silent ecstasy.

When she was done, she rolled over, and the blue mermaid popped out of her butt. “Where do you keep those damn gloves?”

“In a box in the top drawer.”

She ran over to the dresser and put on a pair of gloves with a snap. I lay, exhausted and melting with sexual excitement, naked on the bed as she came back with my ‘Hello Kitty’ in one gloved hand. I knew what she was going to do, and somehow it didn’t bother me at all. I wanted her.

She urgently pushed my legs apart, exposing my sopping wet puss. My clit was throbbing like an over inflated balloon, ready to explode at the slightest touch. She buried two slippery, latex-covered fingers in my hungry cunt, going straight for my g-spot; and at the same time, pressed Hello Kitty to my needy clit. I came like the ocean. I don’t know how long I orgasmed, but when it finally slowed down, I realized I was sobbing.

“Are you ok?”

All I could say was “Wow.”

Wow indeed. Laura told me that I was great, and that she probably wouldn’t be able to sit down for a week. And when she could sit down again, she told me, she would probably bring a riding crop for me to use. Until then, what did I think about a strap-on?

I thought that sounded pretty great.

End