A Friend with Anal Benefits

For a day that completely changed my understanding of sexual ecstasy, it began innocently enough. I was attending the American Library Association’s annual conference in Cambridge, Massachusetts. The keynote speaker on the opening afternoon talked about the virtual libraries of the future and what role librarians would have in them. Afterwards, his audience met in small breakout groups. I found myself sitting next to an extremely attractive guy who was one hundred percent eye candy, complete with bright, carrot-colored hair and deep blue eyes. He appeared to be in his mid-thirties and proved knowledgeable and charmingly funny whenever he spoke. At the end of the session, we walked out together, introduced ourselves, and discovered that we were both staying at the Charles Hotel on the river, a very upscale accommodation that only convention rates made affordable. Neither of us had plans for the evening so we agreed to go dutch at the nearby Legal Seafoods for drinks and dinner at seven.

It was a memorable meal, set against the backdrop of a light fluffy snow falling on Cambridge, making the city look like a scene from “A Christmas Carol.” A perfect martini, generous piece of broiled scrod, and a shared bottle of white wine all helped jump start an easy conversation which revealed that we were about the same age, both reference librarians at large college facilities (he in Minneapolis, I in the Chicago area), both loved to visit the East Coast but preferred to live in the Midwest, both liked to read Hilary Mantel novels, and both were single, largely because we’d never met the right person despite extensive dating.

It must have been the wine, but by the time we got to coffee, I was feeling a little more daring than usual. “Our library,” I said, “puts a special emphasis on validating every research request and helping all students, particularly the younger ones, to feel comfortable asking for assistance on any topic. What’s the most unusual research help you’ve ever been asked for?”

“That’s easy,” he beamed. “I was working the lobby reference desk about two months ago when a senior girl sat down. She was pure Minnesotan. You know the type: really pretty with a perfect complexion, radiating innocence. Her question, however, wasn’t innocent. ‘I’m doing research on ancient Greek vases,’ she explained, ‘and trying to find a book titled Desire: A History of European Sexuality by Anna Clark, but it isn’t in the online catalogue.’ ‘Well,’ I said, ‘we have some excellent books on Greek vases. I’d recommend…’ ‘You don’t understand,’ she broke in. Then, as casually as if she explaining why she had ordered a mocha latte at Starbucks, she continued. ‘I was sitting around with a group of girl friends last week and we discovered that four of us had fwabs.’ ‘What’s a fwab?’, I asked. ‘Oh,’ she replied, ‘I thought everyone knew. You’ve heard of friends with benefits, haven’t you? That’s a couple who hook up to fuck any time they feel the urge. There are tons of couples doing this all over campus. It’s great for study breaks during the week and on Saturday nights. No commitments, just really good sex. Well, a fwab is a total upgrade from that. It’s a friend with ass benefits or, if you’re being polite about it, a friend with anal benefits. When a girl has one of these, she’s hooked up with a very cool dude. He knows what he’s doing and never hurts her so she takes him up her ass any time either of them feel like doing it because it feels so good. When my best friend, Amy, who used to be Ms. Modesty, admitted she had one, I had a brainstorm. My parents used to make fun of “it” as something only guys who were “light in their loafers” did with each other, but now “it” is everywhere. So I’m going to write my honors thesis on a history of anal sex and why societies accept or reject it. I’m starting with the Greeks because what we’d call married men and women apparently ass fucked all the time in ancient Athens. Somebody wrote in Wikipedia that this book had good pictures of the vases that show it.’ Staying calm, I cleared my throat, flipped my monitor to WorldCat and told her that Purdue had the nearest copy, If she filled out the Interlibrary Loan form on our website she’d have it within seven to ten days. ‘That would be great, thanks so much,” she replied and off she went, wiggling her butt across the lobby in a way that suggested that her fwab was one lucky stud.”

“Wow,” I gasped, “that was totally professional on your part. If that had happened to me I would have been so embarrassed I wouldn’t have known what to do.”

It might have been the wine talking in him as well because then he added “what I wanted to say, because it’s the truth, was ‘you can’t shock me and you’re making a mistake if you think I’m some stereotypical nerdy librarian. Maybe you should interview me instead of looking at pictures of Greek vases. I’ve been a butt fucker for almost twenty years, ever since a girl I was dating taught me how to do it the right way.”

Now I was blushing. “I’ve had plenty of experience in bed,” I confessed, “but I’ve never had anal sex.”

“Maybe,” he suggested, starring at me with those beautiful big blues, “I could be your fwab. We’d both have a good time and you could expand your knowledge base. My philosophy about sex is the same as it is about life: don’t leave anything on the table.”

If ever there was a time for a “no thanks” line this was it. The next words out of my mouth should have been “It’s been great having dinner with you, but I’ve got to prep for tomorrow’s presentations. See you at the conference.” Yet I was very tempted. He was gorgeous, funny, honest, and the type of guy with whom I felt absolutely comfortable. Besides, the thought of losing my anal cherry to somebody at an A.L.A. convention who had just announced that he knew “how to do it the right way” was intriguing. It was also snowing and somehow that seemed important. As the old adage went, weren’t we supposed to “seize the day,” or snowy night?

“I don’t know,” I heard myself say. “Wouldn’t it hurt the first time?”

“Not only will it not hurt, you might have the best orgasm of your life. If it makes you feel more comfortable, I promise that the only clothes I’ll take off tonight are my jacket and tie. I won’t unzip my trousers and my dick will never leave my pants. As a matter of fact, you won’t ever see it. That’s too bad because I’ve been told it’s extremely cute.”

“If you promise,” I mumbled, caving in to desire.

“Your room or mine?,” he asked. “I’ve got a queen sized bed.”

“I’ve got a king and besides I’d be much more comfortable there.”

“Why don’t I settle up here, you go get cleaned up, and I’ll meet you in half an hour in…”

” Room 602.”

Thirty minutes was just enough time for a careful cleaning of both my front and rear entrances, a task made so much easier by one of the Charles’s tasteful bidets, and a quick examination of my love bump. It was hot, throbbing, and rock hard, but I showed more self-control than I thought I had and didn’t rub one out right then. Instead, I just changed into jeans and a tank top. Then came the knock on the door.

“Wow,” he exclaimed stepping into the room, “you look beautiful like that.”

He surveyed the room, like a waiter studying a table arrangement. “Let’s set up now so we won’t be interrupted later,” he suggested. With that, he took some pillows from the head of the bed and carefully rolled two together, placing them near its edge. “So you’ll be at a perfect angle for my mouth,” he told me as he tossed a third on the floor, adding “so my knees won’t hurt, I’m going to be on them for a long time.” Then he disappeared into the bathroom, emerging with a towel and a washcloth. He draped the towel over the edge of the bed. “If i do this right,” he explained, “you’re going to cum a great deal, you may even squirt. This is a mattress protector. By the way, which hand do you Jill with?”


“I’m sorry, masturbate. You know Jack and Jill went up a hill, Jack off, Jill off.”

“My left.”

“Then let’s put the washcloth on your right.”

“What’s it for?”

“You may not, but most women I’ve known scream the first time. Not because anything hurts, but because the pleasure and surprise are so intense. These walls are probably hotel-thin and that could be very embarrassing for both of us but particularly you. Just shove the washcloth into your mouth if you feel a scream coming on. There, that should do it,” he continued. “Usually I wouldn’t dream of telling a woman what to do but it is really important to me that you have a great experience. I’m going to try to edge you into something you’ll remember forever, but it’s not going to be like going directly from point A to point B. It’s going to be stop and go, stop and go, and it’s going to take time. Let’s have two ground rules just this time. First, I’m not going to say much and you shouldn’t talk at all unless you absolutely have to. That way you can concentrate on your body and the messages it’s sending to your brain. Second, and this is going to be very hard, you have to agree not to touch your magic button until I let you. If you try to, I’m going to stop you Trust me on this. I’ll know when the perfect moment arrives. Are you O.K. with these rules?”

“Yes,” I mumbled, realizing that he was already right about one thing. Truth to tell, I had already started to cum.

“Let’s watch the passing parade to start,” he suggested as he guided me to the window, leaning me my palms against its cool surface. He stepped behind me, placing his hands on my hips. It was still snowing, but there were scores people hurrying up Brattle Street, past Click and Clack’s law offices, toward the out-of-town newspaper stand and the T. A student couple was moving more slowly, arm in arm past the shops. I was speculating on whether or not the guy was the girl’s fwab when I felt something hard pushing directly on the center of my hole. If he had been playing darts, I thought, he just scored a perfect bull’s eye. This guy wasn’t bragging about knowing how to do things the right way.

The pressure was constant and gentle. Sometimes he thrust slightly forward, sometimes he withdrew, in and out, in and out, a gentle suggestion not as a statement of power. After a couple of minutes, I felt the muscles around my anus relax and open up, just like a flower blooming in the morning sun. They started to contract rhythmically on his dick as if they had a mind all their own. “Fuck me, fuck me, fuck me,” they seemed to say even though they were being stimulated through several layers of clothing. Little waves of pleasure rolled up from my ass as my clit started to ache. As the contractions grew stronger I pressed back against him, trying to clamp down on to his dick and pull it deep into my ass. Gasping for air, my hand moved toward my clit but he caught it by the wrist and gently placed back on the window. “No, we’ve only just started,” he whispered, sticking his tongue into my ear. He stopped, waiting for the contractions to end. When they did, he started again: gently in, gently out, pause; in, out pause; in, out, pause. When my body began to twitch and my legs started to shake violently he led me to the bed where he undressed me slowly.

Once I was naked, he positioned the two pillow under my back, rolled me over on thm, and knelt on the floor between my legs. I felt his tongue on my thigh starting near my knee as he licked the trail of my cum up like a cat laps at a saucer of milk. Up my thigh, over my hole, through my pussy and a quick suck on my clit that made me jump. “Delicious,” he announced, “just delicious.” He must have put his fingers in his mouth because they were wet and slippery when they feathered across my ass cheeks, barely scraping my skin but sending scorching jolts of pleasure directly to my nipples and clit, He blew into my ass, as if it were a balloon that he was filling. Next, he took a finger and covered it with my juice. When it was completely lubed, he scraped his fingernail around the rim of my anus, first clockwise, then counter clockwise. Then he took two fingers and sharply tapped my hole with them. A shock of pleasure coursed through my body and I reached for my clit again. “Play with your nipples instead,” he suggested, “Do it like this and do exactly the same thing when I do let you touch your clit.” He lifted his head and formed his pointer finger and thumb on both hands into small o’s, then snapped his fingers across just the tips of my nipples. I groaned as he went back to his teasing. Touch, blow, scrape, tap, and then the incredible pause that left me twitching and once again gasping for air as I snapped my fingers across my nipples exactly as he had shown me. He waited for my convulsions to stop and when they did went back to resume the pattern: touch, blow, scrape, tap. The shaking returned, even stronger than before. I knew I was losing control of my body, but it felt so good I didn’t care.

The best was yet to come. I couldn’t see it, but felt him form a vacuum with his lips around my ass and suck my hole open. My feet started to flap uncontrollably. His tongue replaced his finger, first teasing the edges of my rim, then licking it from bottom to top and top to bottom. The climax came when he rolled it up into what felt like a little penis and fucked me with it. Nibble, lick, fuck, nibble, lick, fuck, nibble, lick, fuck. Hovering on the edge of reality I looked down. My mind stored an image that will excite me the rest of my life. It was of his bright orange-red head bobbing up and down framed by my thighs and curly brown pubes as he tongued me.

When my whole body started to shake again, I reached for my clit a third time. “Please let me, I can’t stand anymore” I sobbed, breaking my silence. I reached for the washcloth–and this time he didn’t stop me.

It only took three sharp flicks of my finger against my magic button to bring on the explosion. Once again, he had been so right. Something between a scream and a shriek burst out of my mouth, only to be muffled by the washcloth. I remember hovering for a split second in the air with my back arched at a ridiculous angle, and then slamming down into the mattress as an enormous contraction flooded me with release and relief. It was the feeling I get when I really have to pee and think my bladder is going to burst if I don’t and then let go, only ten or twenty times more intense. I don’t remember the second, only the feeling of falling. Lights flashed in front of my eyes as I left the real world.

I wasn’t gone for very long because my next conscious memory was lying in his arms as he stroked my hair while beautiful little jolts still ran through my body. Cuddling up next to him I saw that he had been as good as his word. His zipper had stayed zipped, although a big wet spot on the front of his trousers suggested he had enjoyed himself. “I don’t have to ask if you had fun,” he laughed. “From your belly button to your neck your skin is as pink as newborn baby’s.”

“It was exquisite, just perfect” I sighed. “Put your tongue in my mouth. I want to taste myself.” When he did, l sucked on it harder than I ever did a lollipop as a child, wondering how a tongue could make me feel so good. It smacked of a combination of the minty flavor of my douce and my cum. “You were right,” I agreed. “I do taste delicious.”

Either I couldn’t move or didn’t want to, but I just lay there, feeling such peace and containment as my body started to knit itself back together. “You need a big glass of water to get your fluids back up and then I’ll put you to bed,” he observed as he carried the used linens into the bathroom When he came out he had the water in one hand and another washcloth in the other.. He was right about my being thirsty just as he had been about everything else. I never knew water could taste that good. The washcloth felt warm and damp as he used it to clean me. “It’s under the covers with you,” he announced, tucking me in. For the first time in the evening he kissed me, square on the lips. “See you at the conference in the morning” were his parting words and he was gone.

He might be a librarian by day, I thought as I lay languidly in bed feeling fulfilled in a way I had never experienced before, but he’s an artist at night. His fingers, his lips, and his tongue were his paint brushes and my ass was his canvas. I have a fwab. Fwab, it’s a a funny word, but it would be great for scrabble. I wonder if it will find its way into dictionaries as google did. Next time I’m going to find out if his dick as cute as women says it is. I’ll bet it is. With that, I curled up and fell asleep.

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