Freddie Decides to Finally Try Anal

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I’ve been doing some research about anal sex. For those who require background in my reticence to try anal sex, please read my story, Anal Sex What Is the Big Deal.

I hid in the men’s room at the Logan Airport waiting for a couple gay guys to come in and, you know, and have anal sex. No one came in and finally, I was asked to leave by Mass Port Security. Boy that was embarrassing. I did not dare tell them that I was doing anal sex research. It’s bad enough they thought I was some gay guy waiting for Senator Craig to use the men’s room.

Next, I went to the library to get some books on anal sex. I could not find any books. They had thousands of books on tits and vaginas and penises but nothing anal sex. I was looking for something that had clear and concise, step-by-step instruction with photos and explanations. I did find a book that had a few color pictures of a man boning a woman up the ass. As Confucius said two thousand five hundred years ago, a picture is worth a thousand words.

I walked in the library and stood in front of a matronly looking librarian sitting behind her desk reading a book. She looked to be a woman in her late thirties or early forties but who dressed like she was in her sixties. She looked a little bit like Lily Tomlin when she did that operator comedy routine, you know the one where she snorts while taking your telephone call.

“Where do I find anal sex?”

“Anal sex?” she said smiling and blushing while fanning herself with a copy of D. H. Lawrence’s book, Lady Chatterley. “You want anal sex?”

“No, well, yeah. Sorry,” I said, “I didn’t mean to offend you.”

“Oh, no offense taken, big boy,” she said with a wink and staring down at the big bulge my love tool made in my pants.

“Allow me to rephrase my question.” I smiled thinking how to put it delicately. “Where do I find some ass play?”

She wiggled in her chair, crossed and uncrossed her legs, and tossed Lady Chatterley in the long overdue pile.

“Meet me in the back by the encyclopedias in five minutes. None of the illiterates go there anymore with the advent of the Internet,” she said coyly smiling at me. “I will show you all that I have…” she smiled and winked, “on ass play.”

What did I know? I figured she had a secret stash of anal books hidden away there; something from the 1800’s where they did more of that stuff, probably, as a method of birth control. Yet, when I walked over to the far corner after waiting the required five minutes, there she was with her skirt and panties down around her ankles, bent over with her ass up in the air, and wagging her round, white ass at me.

“Hey, lady, I only wanted a book on ass play and not a demonstration of it.”

“You can only learn so much from books,” she said looking out at me from in-between her legs. “Sometimes you have to do instead of read.” She wiggled her ass. “C’mon big boy stick it up Mommy’s ass.”

“Yeah, well, tell that to Literotica,” I said storming out.

“Literotica,” she said, “he frequents my favorite site.” She pulled up her panties and skirt and ran out the door after me. “Oh, my dreamboat has finally docked.”

She chased me six blocks before I finally lost her in a group of Nuns. I was shocked to overhear their conversation. All this time, I figured that Nuns and Priests talked about religion, about God, about helping the poor, and feeding the hungry. I figured wrong.

“Then, Father güvenilir bahis Flanagan came in to the convent and into my bedroom again looking for his lost cigar. I knew what he wanted but I played along with him. You’ll not find what you are looking for under my bed, I said, Father Flanagan. Perhaps, you will find it beneath my nightgown, whereupon, pretending to pray to the Lord All Mighty, I assumed the position, on my knees with my naked ass in the air. Ah, there it is, Sister Maureen, he said, with a poke and a probe, as he stuck his pink cigar deep up my holiest of holes.”

I so wanted to ask the Sisters for advice in trying anal sex for the first time but they were a scary bunch. They all so looked alike and every one of them had a mean expression on their face that women sometimes get when they haven’t been laid in a while. I was afraid of them and afraid that they would rape me or worse convert me.

Next, I convinced my hairstylist who is also my girlfriend’s hairdresser to come home with me and help me with the first time that I was to have anal sex with my girlfriend.

“Honey, I’m home.” I turned to Vincent and put my fingers to my lips, “Shh. And you’ll never guess who I met on the way home.”

“Who, Honey? Tell me you met Brad Pitt. God, I love him. I would get down on my knees and suck his cock.”

“Vincent. I met Vincent our hair care person.”

“Oh, that big, flaming fag. Where’d you meet him at the mall men’s room where he was boning someone up the ass or blowing someone in a parked car?”

My mouth dropped to my knees.

“Honey, Vincent is here…with me…now.”

“Hi, Donna,” said Vincent when Donna walked in the room topless. He put a hand on his side and pushed out his hip. “Yeah, he brought the big, flaming fag home.”

“Oh, Vincent,” she said turning a bright red. “I was just having a bit of fun with you. I knew you were here all along.”

“And that is why you came out to the living room with your tits on display.”

Donna looked down at herself, turned beat red, again, and covered her tits with her hands. Vincent took a step forward. Let me see those, again, Sweetie. Donna dropped her hands as Vincent felt her breasts.

“Are they real?” His hands were all over her tits, fingering her nipples, feeling the weight of them in the palm of his hand, and squeezing them. He did everything but suck them. Donna was flushed from him playing with her tits.

Geez, gay guys can get away with anything. It makes me want to pretend to be gay so that I can go around feeling up women.

“Hey, get your hand off my ass.”

“It’s okay Lady, I’m a gay man.”


Donna excused herself to get a bra and blouse.

“Would you like some coffee, Vincent,” said Donna now being super nice to him. “I brewed some fresh.”

“Sure that would be wonderful, Sweetie.”

Vincent called everyone Sweetie, even me.

We sat and chatted. Vincent looked at Donna’s hair and walked over to her fluffing it out with his hands.

“What are you using on your hair, Sweetie? It’s so dry.”

“The same shampoo that I have always used.”

“I have a new line of hair care products that is fabulous. The next time you are at the salon remind me.”

Then, he looked at my hair and waved a hand of despair.

“You, you’re a hopeless cause. What do you use on your hair a roller brush, a bit of hair spray, and mousse?

“Nah, türkçe bahis water, a comb, and a baseball cap.”

“See, guys are all the same. I wish I was not so vain. I would save a fortune on face cream alone.”

Donna looked at me and I looked at her and we both looked at Vincent. I knew she wondered why I brought home the big, flaming fag. Actually, I liked Vincent. He was funny, witty, and smart and I viewed him as my friend. So long as he kept his hands and penis to himself, why should it bother me that he was gay? It’s his life and he has a right to follow his happiness. That’s what this great country is all about, the pursuit of happiness.

I think women are sometimes jealous of gay men because they take so many beautiful men off the market. She really couldn’t stand him but he was a wonderful hairdresser. He was just too gay for her. He offended her with his tight pedal pushers, flip flop shoes, and outrageous frilly blouses that the excess lace of his sleeves always hit her in the face when he was sash-shaying around her fixing and fussing with her hair. I suspect she did not like him because he looked better than she did.

“Honey,” I said, sensing her ill at ease and her patience waning. “I asked Vincent here to help us.”

“Help us?” She looked at Vincent. “Help us do what?” She looked to me and then to Vincent and back to me.

“Well, you know how we’ve been talking about trying anal sex—”

“Freddie! I won’t discuss my personal and very private sex life in front of my hairdresser.” She turned to Vincent, “No offense, Vincent, but I don’t want my sex life used as pubic gossip and speculation all over the salon.”

“Oh, I don’t blame you Sweetie,” he said crossing his legs and waving a gay hand at her. How does he do that? Crossing my legs like that would crush my balls and rupture me? “This is too juicy to keep to myself.”

“Fucking idiot,” she screamed at me.

Donna looked at me and made a face like she just bitten into a lemon. I can’t figure out women. Here I was sincere in my thought and trying to do something nice for my sweetheart to get our lustful desires burning again and she turns on me.

“So, that’s what this is all about, Freddie?” Now, Vincent was looking at me like he just bitten into a lemon. “You brought me here to humiliate me thinking that as I gay man that I know all about anal sex?” He fluffed his hair and wiggled in his seat as if just the thought of having anal sex was making him hot. “Well, I’m flattered but am still very furious with you, very furious.” He touched my hand and said with a laugh. “If you weren’t so cute, I’d really be mad.” He reached over and tweaked my cheek. I was glad it was my face cheek and not my ass cheek.

Suddenly, Donna looked calm, peaceful, and happy and it was then that I realized that she saw my gesture as good, thoughtful, and sincere. Only, I was so wrong. She looked over at Vincent and smiled.


“Yes, Sweetie.”

“Why don’t you take Freddie into our bedroom and show him how to do anal sex?”

I thought Vincent was going to cream his pedal pushers.

“Oh, I would be happy to assist Freddie and break his cherry.” Vincent took my hand and stood. “C’mon, Sweetie, let Vincent show you how real men do it.”

“No, no,” I said looking at Donna like I had just bitten into a bushel of lemons. “You have this all wrong. The anal sex is not for me, well it güvenilir bahis siteleri is for me, but I am the giver and not the taker.”

“Well, if that is what you want, Sweetie, you can stick that big thing up my ass any time.”

I ignored Vincent’s distasteful comment and smiled at Donna before looking over at Vincent.

“Why don’t you take my lovely girlfriend in the bedroom and fuck her up the ass while I watch and videotape it. Then, I can post it on the Internet so we all can enjoy it.”

Now, both Vincent and Donna looked at me like they had just bitten into a bushel of lemons.

“Oh, no, that would never do, dear Freddie,” said Vincent letting go of my hand, sitting down, and lightly touching his hair with an experienced hand. “I preferred the big, muscular types much like you and not the little bitchy things like your boney girlfriend over there,” he said with a wave of his finger toward Donna.

“Oh, no, that would never work, fuck face, er, I mean, Freddie dearest,” said Donna gritting her teeth and making a fist. “I prefer a real man and not one who wiggles his ass more than Marilyn Monroe while masquerading as Madonna.”

“Oh,” said Vincent sitting bolt upright, “do you really think that I look like Madonna?”

Geez, you could not bash the guy. He took everything as a compliment.

Well, Vincent left and I convinced Donna to try out what I learned over the course of my day of research.

“Okay,” I said, “you sit there and I ask you where I do I find some ass play?”

“Yeah, then, what?”

“Let’s see. You bend over in the far corner of the room with your pants and panties down around your ankles and with your back side way up in the air while wiggling your ass.

“I’m not going to do that you big jerk. What the fuck is wrong with you?”

“Okay, okay, let’s try something else.” I paced the room trying to remember the conversation that I overheard between the Nuns. “Lay on the bed. Please? C’mon, just humor me and lay on the bed.”

“Okay, I’m on the bed.” She looked bored to tears. “Now what?”

I walked to the bedroom door.

“Okay, now, I walk in the room and say, where’s my cigar? I lost it around here somewhere.”

“What? Cigar? What cigar? You don’t even smoke. You’re insane. I’m not doing this. It’s retarded.”

“C’mon, c’mon, I know this will work. Sister Maureen and Father Flanagan…” I looked at the pained expression on my devout Catholic girl had on her face and decided not to divulge my sources. Just say this, you won’t find your cigar beneath my bed Father, er, Freddie. Why don’t you look under my nightgown? Then, pull your pants and panties down and stay on your knees with your ass in the air as if you are praying, er contemplating.”

“Yeah, before I do that, then what?”

“Then, what?” I scratched my head. “I dunno. I didn’t get that far. Where’s the book that I brought home from the library. It has a picture, there, see, the guy takes a position behind the woman with his pants down around his ankles.” I stripped off my pants. “Lemme see that picture again. Okay, I get close to your ass with my penis and—”

“Listen let me know when you figure this out, Einstein. I’m going to make myself a drink. Do you want one?”

“Yeah, make me a Pain-in-the-ass.”

“Pain-in-the-ass? What the Hell is that? Me? Are you calling me a pain-in-the ass, you sack of shit.”

“No, no, Pain-in-the-ass is a drink. It’s Bacardi 151 proof rum, Malibu coconut rum, Midori Melon liquor, Dekuper Sour Apple Pucker schnapps, pineapple juice, and 7-Up soda.”

“Make it yourself, asshole.”

This anal sex is not working out for me.

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