Introduction to Anal Sex (Sort Of)

I saw her the first day she came to work. She was tallish, not very pretty (in fact, kinda ugly) but she had a body to die for. Her tits were full, way bigger than a handful. She wore a black pencil skirt that showed her very shapely legs, hips and ass to perfection. She was thick without being at all overweight. Like I said, a body to die for.

Her name was Marian. We met and chatted a few times in her early days working with us and I found her quite charming and fun to be with. So I asked her out. She agreed and so begins our story.

I took her to a small Italian place not far from work. They seated us at a quiet table away from the crowd. We were able to chat comfortably without worrying about others hearing us. We ordered dinner and while we waited, we made small talk. From time to time she would lay her hand upon on mine, and once even rested her hand on my thigh. Dinner came, she touched my hand, I held it and moved our hands below the table while they gave us our food. From that moment on we were touching or holding hands.

When we finished, they took our plates away and we ordered dessert. She unbuttoned the top two buttons on her blouse and leaned forward onto her folded arms. Her cleavage swelled up like a couple of inflating balloons. It took my breath away. I took a chance; "Those are beautiful. I hope you are showing them for me."

She smiled, "Of course I'm showing them for you. I'm glad you like them. I've done this before, but most guys are afraid to acknowledge them up front. You're bold."

I squeezed her hand and said, "Fact is, your tits were the first things that caught my eye, the first reasons I wanted to get to know you. Does that offend you?"

"Not at all. All straight men are attracted to my boobs. Few are willing to admit it. And none as boldly as you. Are you interested in more?"

Dessert came and cut our conversation short. I said that I was certainly interested in more. I wanted to get to know her better and to get to know her body better, as well. This time I put my hand on her thigh. And squeezed.

We started dessert and she asked, "And what do you hope to learn about me and my body? There's a lot there." She giggled.

"What you like and what you don't like, your favorite color and how soon after rising do you eat breakfast. I'd like to know what you sound like when you orgasm. I'd like to know about things you've tried and liked or didn't like. About things you haven't tried but would like to. Stuff like that."

She moved closer so she could speak softly. "I like oral sex a lot. Giving and receiving. In my experience, though, too many men are big on the receiving and not so much on the giving. How about you?"

I grinned ear to ear. "I like both, you betcha. I love a good blowjob as much as any man, but I like eating pussy almost as much. Not much better than a woman cumming in my mouth while I'm eating her pussy."

"I can't believe how dirty you talk. I really like it. You are bold."

"Well, you opened the door. I just walked in."

"So, what do you like? Sexually, I mean."

I raised my hands in a 'Who knows?' gesture and said, "I like 'most everything I've ever tried. But I suppose what gets my fires burning more than anything is anal sex. Giving and receiving. Receiving more than giving."

She raised her eyebrows, "You've been fucked in the ass?"

"Not by a guy, but I've had women give me fingers, tongues, dildos and toys up my ass, and I love it. Straight up, pardon the pun."

"I've tried anal before and I didn't like it. But I never imagined trying it on a man. It sounds hot. I think I'd like to try that. You really enjoy that, do you?"

"I really enjoy it. A lot." I told her, hopefully, "The one thing I'd like to try, but haven't, is a strap-on fuck."

"A strap-on fuck?"

"A woman wears a special harness around her waist and thighs with a cock-like dildo attached. It allows her to be equipped somewhat like a man. So equipped, she ass fucks me. Sound like fun?"

Skeptically, "And you think you would like this? A woman fucking you with a strap-on... thing?"

"I don't know, but I'd sure like to find out. You interested?"

She collapsed back into her chair. She gave me the same 'Who knows?' gesture I used earlier. She looked a little flustered and perhaps, a bit out of her depth. "I kinda want to, but this is so far beyond anything I've ever tried before. I don't know. Do you have such a device? Where would you even get one?"

I used my finger to call her closer. She sat up and moved closer so I could whisper, "At a sex shop."

"A sex shop? I've never been to one. Is there one here in town?"

I looked at her incredulously, "You've never been to a sex shop? This could be an interesting evening. A sex shop is where you buy sex stuff. Toys, movies, lingerie, gear. Anything you would need for a sexual adventure. There's one close by here. Let's go check it out after we're done here."

"Sounds like an adventure. Let's go."

So we drove over to Suzie's Sex Shop. There were 5 or 6 cars in the parking lot, So I figured there would be people in the store, but not many. Marian was very nervous as I helped out of my car. "Are you sure? Is it nasty inside? Perverts jacking off and stuff?"

I gave her a kiss on the cheek and pat on her shoulder, "It's nice inside, and I've never seen anything more than a man adjusting his pants. If you know what I mean."

We went in and I think Marian was very surprised by the place. Well lighted, the clerk greeted us when we came in, everything was orderly. Just like any other kind of shop. As we walked up and down the aisles, she began get over her embarrassment and became really curious. She started to look at the items in the counters and on the shelves, even commenting and giggling about some of them.

We stopped at a rack displaying adult DVDs. I saw one cover with a well-endowed naked woman looking at the camera. A handsome man stood behind her with his arm around her, holding one of her tits. Cool. I showed her the picture, asked her what she thought, and wrapped my arm around to grab her tit just like the man she was looking at. She sighed, laid her head back on my shoulder, brought her hand up to mine and gave it a squeeze.

She turned around and gave me a hug. She whispered, "I've never done anything like that in a place where people might see me. So naughty." So for most of the rest of the time in the shop I had a hand on her body. Mostly her ass, but I would squeeze one of her tits when it seemed warranted.

We wandered around the shop until we found the strap-on dildos. There were about a dozen to choose from and most of them looked pretty hot. But the prices! They all cost a whole lot more than I was prepared to spend that night. We kept looking. On the next display over were the regular dildos. Everything you could imagine; realistic or smooth, large or small, vibrating or still, on and on. Finally, there it was. 14 or 15 inches in length, dark red, translucent, with a realistic cock head on either end. A double headed dildo. One third the price of the strap-ons, but capable getting the job done. I took the package off the hook and showed it to Marian.

"I know this is not a strap-on like I suggested, but those were so expensive and I think this baby will do the trick. What do you think?"

I showed her the dildo and slid my hand around to feel her ass. She touched the dildo with her fingertips, running them up and down to assess the feel. Again, she lay her head on my shoulder, "I like it. But I don't care. I'm so horny right now, I don't care what you get. I just want to get started. Let's go."

With that, I walked up to the counter to complete the purchase. An attractive young woman waited on me. I told her, "I'd like a tube of Anal-Eze and a one use, disposable enema, please." She rang up the transaction, I paid her, and she bagged the stuff.

She said, "I have a fair idea how this all will be used. I've been wanting to try it myself. Would you please come back some time and tell me how it went? I work 5 evenings a week, so I'm usually here." She winked.

I smiled, nodded my head and left to find Marian. She held my arm with both hands and we walked out to the car. We agreed that her place was closer, so that's where we went.

She opened the door to her apartment, she signaled for me to enter, and she followed me in. Her apartment was small, clean and very well kept. When she closed the door, I grabbed her to give her a hug and a kiss, she put her hand on my chest and said, "Wait."

OK, wait for what? I backed off and she asked me to sit down. "You will find this hard to believe. I have a ritual, if you will, that I perform before sex. We're going to make love tonight, yes?" I nodded. "We're going to fuck." Again, I nodded. Before we do any of that I'm going to give you a blowjob. I'm going to suck your cock until you cum in my mouth. It's not foreplay, it's not a warmup. It's just a quirk. Guys find this a bit confusing, unusual, but none refuse. Are you up for it?" I nodded.

She dropped to her knees in front of me, spread my legs open and opened my pants. She pulled out my stiffening cock and put it right into her mouth. I don't have a particularly large cock, so she was able push her mouth right down to my pubes. And then she got busy. Between the surprise of it all and her skill, it didn't take long for me to cum. I shot into her mouth. She made a noise between a hum and a moan. She swallowed and sucked, swallowed and sucked until everything was down her throat. It was a blowjob to remember. When it was done, she sat back on her heels and smiled. "I hope you liked it. I did." I nodded. She brought down her eyebrows. She set her mouth. "Now we can fuck."

We both stood up and embraced, kissed. But with less urgency because I had just cum. I thought she might be on to something. I caressed her tits and squeezed her ass cheek. We kissed. But it was softer, more loving, unlike any first time I had ever done before. Women out there, think about this next time. If you want the kind of tender loving you crave, suck him off first.

"I'm going to go change." She left for her bedroom. I went to the bathroom to complete my ablutions and returned in my boxer shorts. She came out a moment later looking very sexy, indeed. She wore a light green chiffon tube top that was only gathered above her bust. The material draped down loosely over her tits, leaving easy access to the prizes inside. Her bottoms were not much more than chiffon boxer shorts. Again, gathered at the top but draping down with no effort to hide any of her treasures down there.

I stood up, gave her light kiss, and took both of her magnificent tits in my hands. She looked me right in the eye as I squeezed, rubbed and tweaked them. "I'm in debt to you," I whispered, biting and licking her ear. "You showed me you could give oral. Now let's see how you are about receiving."

We walked to her bedroom and she lay on the bed. I spread her legs open, moved some fabric aside, and gazed up a very wet and open pussy. She was ready. I licked her labia and easily found her deep hole. I pushed my tongue as far down her as I could. In and out. I even paid attention to her pee hole. Her moaning and squirming told me I was on the right track. I moved up and sucked her clit into my mouth, swirling my tongue around it. She grunted and grabbed my head with both hands, pulling me hard onto her pussy. I kept sucking and licking her clit and before long she started cumming. Cumming wet and messy. I loved it. When she calmed down a little, I let go of her clit and moved up to kiss her. Before our mouths met, she began kissing and licking all over my face.

"You like the taste of your pussy on my face?"

"I love it, especially right after I cum. Now shut up and let me finish cleaning."

We lay back and relaxed in the glow. I was on my side and I could gently play with her tits. I was delighted to watch the material on her tube top rise and fall as moved my hand around.

Marian kisses me, sits up and says, "I'm getting eager to try this new toy. Let's get this thing warmed up." Sounded good to me so I grabbed the bag, pulled out the lube and opened the dildo packaging. It looked awfully big now that I held it in my hand. She held it and grinned.

I got up on my hands and knees and handed her the Anal-Eze lube and said, "Put some on your finger and rub it around my asshole, start getting it loose and relaxed." She did as I asked. "Get a larger dollop and begin pushing it into my asshole. Push your finger in and rub it all around." She did as I asked and it was really feeling good. "Now, get some more lube and use two fingers."

I explained she needed to get my hole relaxed and open so that the dildo would fit inside without too much pain. She put some more lube in and really started working my hole. Twisting her ringers around, pushing them in and out, she added a third finger. I think she was enjoying this.

"Are you having fun back there?"

"I'm loving this. No man has ever let me play like this. Am I doing it right?"

"It should be getting real slippery by now. Almost like a wet pussy. If not, put in more lube." I could feel her squeezing more lube on my hole and using her fingers to spread it in and around. She was doing great.

"Now, spread some lube around the first few inches of the toy. Let me know when you're ready to start."

"I guess I'm as ready as I'll ever be."

She laid the tip of toy against my rosebud and began gently pushing it in. It hurt a little bit but it wasn't bad. I pushed my butt back onto the toy and she continued pushing it in. I asked her to stop for a minute and let me relax.

"How far in is it? It feels pretty good, so far."

"It's almost 2 inches in," she said. "It looks really hot to me."

"Push it in another inch," I said. She did, and it didn't really hurt, but my butt just felt fuller. "Further." She did, it started getting good to me. I pushed back.

"Alright, pull in back and push it back in gently. Again. Again." The was awesome and I was loving it and I told her so, repeatedly. She was actually fucking my ass with that big dildo, and I just wanted more.

"OK, Marian, this is great. Now it's your turn to play. Hold the toy so it doesn't fall out while I roll over onto my back." I slowly rolled over and got comfortable on my back. "Now slide your end into your pussy and move as close to me as possible."

She pushed the head of the toy into her pussy and began sliding towards me to push it further and further up. We were scissoring and she got close enough that we were almost 'bumping uglies'. And she said, "This feels so fucking good. How come I've never tried this before?"

I said, "Let's fuck." We began to rock back and forth, up and down and any other way we could try. It took a while but we finally found a rhythm. And what a rhythm it was. We each wanted to fuck the other as hard as we could while also being fucked. Here we had two givers and two receivers in the same fuck. Beat that.

We enjoyed this new kind of fucking for a few minutes. Marian came 2 or 3 times and I was sure wanting to pop, so I grabbed my cock and started jacking. She saw me and asked me to stop. She wanted to suck me off while this cock was still in my ass.

"OK let's wait until you cum again and we'll switch."

Shortly, she came, real hard. We stopped to let her rest. After a minute she pulled the toy from her pussy. She leaned over me, rested her hand on my cock, kissed me and whispered, "I hope you enjoy this orgasm as much as I've enjoyed mine." She moved her head back down and took my cock into her mouth. She sucked my cock and slid the toy in and out of my ass. Heaven.

It didn't take long for me to cum. My whole body shook as I blasted cum into her mouth. She sucked and swallowed until she got it all. She kept sucking until I went limp. With my limp cock still in her mouth, she lay her head on my thighs and slowly pulled the dildo from my asshole. It felt better coming out than it did going in. The pleasure just didn't stop.

After a bit we got untangled and she rolled over so I could be the 'big spoon'. I reached around and gently played with her tits. She moaned and wiggled her butt around my cock. What a nice way to come down.

"Thank you for that. I've been wanting to try something like that for some time. You seemed to enjoy it."

Marian laughed. "Are you kidding? That was wilder than anything I ever imagined. To watch something I was holding fuck you in the ass was awesome. I hope we can do it again. Know something else? After you showed me how to prepare the asshole before entering, I got to thinking, with your help, I'd like to give anal sex another try. You interested?"

"Very interested." I gave her anus a gentle poke and rub. She giggled. "Remember how much you enjoyed me touching you in she sex shop, knowing that people could be watching?" She smiled and nodded. "How would you like to try what we just did in a room where people will definitely be watching? And we would watch them? Think about it."

With that we snuggled some more and drifted off to sleep.