Doug Finds Out The Hard Way

Marian had suggested that I invite a friend over for dinner and who knows what else. So next evening, my friend, Doug and I let ourselves in to Marian's apartment. As soon as we entered the living room, the heavenly aroma of dinner overwhelmed our senses. I smiled and said, "This is gonna be great."

Marian came out of the kitchen to greet us. She was wearing shorts and a tee shirt, no bra. Her large tits filled her shirt nearly to capacity, her nipples poking out nicely. Doug caught his breath. I see Marian like this all the time, so I just smiled.

She stepped up to me and gave me a nice kiss, bringing my hand up to hold and squeeze her left tit. "Who's our handsome guest?"

"Marian, this is my friend, Doug. Doug, this is Marian." Without releasing my hand from her tit, Marian made a half-turn towards Doug and extended her right hand in welcome.

Marian smiled. "Pleased to meet you Doug, and welcome to my home. Please, guys, have a seat." With that she released my hand from her tit, and I sat down in the chair. Doug sat in what I had come to call the 'blowjob seat' on the couch.

"Couple a' beers?" She asked. Doug and I nodded, and Marian headed off to the kitchen.

Doug looked at me questioningly, spreading his hands in a classic "Whaaaaaat?" pose. I waved my hand nonchalantly as if to say, "Don't worry about it. It'll be OK." Doug shook his head and sat back in his seat.

Marian returned with our beers and handed one to me. She turned to Doug, gave him the other and said, "Doug, dinner will be another 20 or 30 minutes. Would you like a blowjob while you wait?"

It's a good thing Doug hadn't drank any beer yet, or we might have had a nice sputter mess. As it was, he sat up and said, "What? Seriously? A Blowjob?"

Marian smiled. "Yep. We've got time."

Doug managed to slow his breathing. He looked at me and back at Marian just to see if this was a joke or something. He said, "It's not my practice to turn down a blowjob, no matter the circumstances, so, yes, I'd love to have a blowjob while waiting for dinner. We just met, but, hell, why not?"

She laughed. "Oh, it's not me. I've got to get dinner done. I mean, I'd love to, but I'm just too busy right now. Hang on." With that, Marian turned towards the back of the apartment and hollered, "Robyn. Robyn, come on out here, honey."

Robyn came out a moment later. Sexy as hell, wearing Bermuda shorts and a way too small tank top that both covered and displayed her tits at the same time. She also wore her wig and a modest bit of make-up that took the edge off of her homeliness. This had become her signature look.

She came over and gave me a peck on the cheek and then turned around and just stood in front of Doug. Marian said, "Dinner will be about 20 minutes or so, can you give Matt's friend, Doug a blowjob while he waits?"

"Sure. I'd love to."

Marian returned to the kitchen.

Robyn bent down to give me a kiss and whispered in my ear, "Is this really OK? You want me to do this?"

I kissed her back and whispered, "It's really OK. Go. Have fun."

Robyn got on her knees between Doug's legs and began to open up his pants. Doug looked at me, "Really?" I nodded.

Robyn pulled Doug's already stiff cock out of his pants, looked at me and winked. She wrapped her lips around his cock and went to town. Her hand was working up and down in time with her mouth and I knew that this one wasn't going to last long. I'd had my cock in her mouth many times and I knew how 'persuasive' she could be. I glanced over and saw Marian watching from the kitchen, smiling.

Doug rested his head back on the couch cushions, making noises that indicated that he was enjoying himself. Robyn sped up the pace of her bobbing and I knew that when she sped up, she also gripped the cock a little tighter. This one was coming to an end pretty soon.

A minute or two later, Doug lifted up his hips and let out an elongated "Ooooooh" and Robyn stopped bobbing and pressed her face further down into Doug's lap. Doug was firing. After a few moments, he collapsed back down onto the couch and threw his head back in relief. Robyn stayed where she was, sucking up the last of Doug's cum and letting his cock go soft.

Robyn sat back on her heels and said, "Wow, Doug. That was great. Thanks."

"You're thanking me?" Doug began straightening his pants. "I should be thanking you. That was great."

"You liked it? Good, I hoped you would." She looked at me. "Matt, he liked it."

I beckoned her over to me and took her hands. "Of course he did. I've told you before, you are an excellent cock sucker and with experience you'll just get better. Now, dinner's will be on the table soon, so go get ready." I patted her butt, and she left for her room.

There was silence for a minute or two. Doug looked at me, slapped his hands on his thighs and said, "Well, that was unexpected. Lovely, but unexpected."

I chuckled. "But I bet you liked it." He nodded. "I asked you over for this for a couple of reasons. First, I figured you might just like it. But more importantly, I think I can count on your discretion. What happens here, stays here. OK?"

He shook his head. "I got it. Thank you and you can count on my discretion. Bet that."

I said, "Good. In that case, if you're interested, the night is still young." I dropped my voice to a fake whisper. "I think Marian likes you."

Marian hollered from the kitchen, "I heard that."

We both chuckled.

For the next few minutes, Doug and I talked about work, cars, politics, just about anything except what was going on here tonight.

Finally, Marian called out, "Dinner's ready. Come to the table, guys." A little louder, "Robyn, come on out, dinner's on the table." We all sat down to a large bowl of spaghetti with meat sauce, a loaf of garlic bread and a nice bottle of Chianti. It looked and smelled delicious.

I said, "Let's tuck in." And tuck in we did. We all enjoyed a great meal.

As we finished up, Marian asked Doug, "How was everything, Doug? Spaghetti to your liking?"

Doug wiped his lips with his napkin and said, "Everything was great, Marian. Just excellent. But I'd like to say, I certainly wasn't expecting and I'm not sure what to say about the before dinner treat."

Marian said softly, "Go ahead, Robyn. Go on."

Robyn looked at Marian and then down at her lap. She finally looked up at Doug. "I'm glad you liked it, Doug." Blushing. Softly, "You're the first guy that I sucked off so soon after meeting him. Almost like sucking a stranger.:

Doug stammered, "I...I...I don't know what to say."

"Then say nothing," quipped Marian. "You and I can retire to the living room and talk all about it, as well as get better acquainted. Matt, you and Robyn clean up in here, OK?"

Marian and Doug went one way, and Robyn and I went the other. When we got to the kitchen, I pulled Robyn into my arms, squeezed her butt and gave her a big kiss. "You were great this evening. I'm very proud of you. I suspect that there's going to be a lot more blowjobs in your future." I laughed.

Robyn smiled and turned to the sink. "Oh, yeah."

Clean up took 20 minutes or so and when we were done, Robyn and I headed out to the living room. Marian and Doug had indeed gotten better acquainted. She was sitting in the 'blowjob seat' of the couch, naked with her legs spread wide. Doug was on his knees eating her pussy with enthusiasm. Her eyes were mostly rolled up into her skull. We didn't want to interrupt.

We stood watching and Robyn shoved her hand down her shorts and played with her pussy. I stood behind her, squeezed her tits and nibbled on her ear. She rested her head back on my shoulder and moaned, softly.

I whispered, "Shall we join them?" Without saying anything, Robyn quickly got undressed. Naked, she sat on the other end of the couch and spread her legs wide. I got on my knees and began eating her pussy with enthusiasm.

Now by the time Robyn and I had joined them, Marian and Doug had been at it for bit and were ready for a change. So, when she came the next time, Marian suggested that she and Doug head to the bed for new treats. They untangled themselves and got up from the couch. As they turned down the hallway, I heard Marian ask, "Are you ready for some butt?" I didn't hear Doug's response, but I was rooting for Marian.

Robyn and I carried on until she, too, was ready for something else. She came one more time and then pulled me up onto the couch next to her. We kissed and she began licking her pussy juice from my face. After getting it all, she said, "Mmmm, you're right. I do taste good." I chuckled. "What Mom said inspired me, though. You haven't ploughed my butthole in some time. Want to fix that?"

With that I got up, held my hand out to her and said, "What are we waiting for? Shall we join Marian and Doug, or go private?"

"Oh, private, for sure. I want to try something new. Are you up for it?"

I looked down at my erect cock. "Um, yeah. I think so. If it begins to flag, I'm sure you'll be up to the task of getting it back "up".

"Cool. Let's go. I love getting you "up" for stuff." She took my hand and stood up from the couch. It was a very short walk to her bedroom.

Robyn was already undressed, so she just jumped up on the bed and set against the headboard. She spread your legs open and began playing with herself. I'd have been in bed sooner but watching her made it difficult to focus on getting my own clothes off. Hell, I still had my shoes on. But get undressed I did. I hopped up on the bed and wrapped Robyn in my arms and we kissed each other and explored each other's bodies and had a grand old time.

After I was good and "up" I broke our embrace and asked, "So what's this something new you want to try? I like new stuff. I'm glad you do, too."

"Well, you lay on your back with your cock pointing up. I aim it at my butt hole and slide down on it and we fuck our brains out. How's that sound?"

I smiled. "Sounds like fun. The position is called 'cowgirl' because of the way she straddles the man like she's riding a horse. I've done it before but only in the pussy. And I've only ever seen pictures of it done in the pussy. Where'd you get the idea to do it anally? Not that I'm complaining. I can't wait to try it."

"A girlfriend has a magazine with pictures of it. You can clearly see that it's done in the butt. I thought it looked hot."

I shook my head ruefully. "Kids these days. She must be a wild thing to keep magazines like that around."

Robyn laughed liked she's heard a great joke. "She's still a virgin. She's never even kissed a boy. She and I kiss a little, but she won't touch my boob or let me touch her's. The closest she gets to sex is swiping her dad's magazine's and imagining herself in those situations. She doesn't even masturbate. It's kinda sad."

"Does she know that you're going to try 'cowgirl anal'".

Robyn shook her head vigorously. "She has no idea the life I lead. She thinks our kissing is the sexiest I get. It's nice to have a normal friend, so I let her keep thinking of me that way."

I reached over, squeezed a tit and kissed her. "So. How do you want to do this? Shall I enter you doggy style and then shift or what?"

She sat up. "No. You lube up my butt hole really good and then lay on your back. I'll lower my pussy onto your cock and get you nice and wet. I'll lift up and slide the tip of your cock to my back hole, line it up really good and slide down. At least that's how I imagine it."

I slapped her lightly on her butt and said, "Alright, get on your hands and knees and I'll lube you up right."

She assumed the position; I grabbed a tube of lube from the dresser and got busy lubing. I got a small dollop of lube on my fingertip and gently swirled it around her sphincter, applying gentle pressure to the hole but not enough to sip in. I got a larger dollop and began gently pushing the lube into the hole without actually pushing my finger in. I finally squirted a good bit of lube right onto her hole. This time as I pushed the lube in, I pushed my finger in up to the second knuckle, twisting about spreading the lube all around the inside of her butt hole. All the while she's softly singing and humming, "Oh, yeah. Just like that. Oh, oh, oh. That's right. Oooh, deeper." That sort of thing. I think she liked it.

So I slapped her gently on the butt again and said, "So, let's see how this goes." I rolled over onto my back, held my cock up a little and said, "Hop on."

She leaned over my body and swung one leg over me so that she straddled me at the waist. She folded her feet under her thighs, so she rested on her knees. Before she did anything else, she leaned down and kissed me. "Let's have some fun."

With that she held my cock and slipped it into her pussy and slid down until I was all the way in. It took my breath away it felt to nice. Judging from her long "Oooooh" I'd say she liked it, too. She started rocking back and forth and it was clear that this was pushing some pretty happy buttons. I kissed her, "If you're happy with this, we can keep on and do the other thing another time. This is pretty great."

She stopped rocking. "Oh, no, no, no. We're doing the anal. But, like all the other sex we've had, I've done this with other guys, but you're just better. I got carried away for a second. I guess it's time for step two." She leaned down and kissed me.

Robyn lifted her body up until my cock slipped from her pussy. She grabbed it and lined it up with her rosebud. Taking a deep breath, she pushed down until the head of my cock just entered her hole. She waited a moment and said, "Here goes." She relaxed her legs and allowed the weight of her body to push her butt down onto my cock. My cock slid in all the way in one movement. It was a most luxurious feeling. Tight at the opening, warm and smooth down the inside. It was without question the best way, the sexiest way I'd ever entered a woman's ass.

She rested for a moment after she hit bottom. She held my shoulders down with her hands, looked dreamily into my eyes and breathlessly said, "That was awesome. I love it in my ass, but that was a whole different thing. Gentle, yes. But once I relaxed it felt inevitable. It was like I was falling onto your cock, and I couldn't stop it. Never felt anything better." She caught her breath for a moment and said, "Now let's fuck."

She began rocking up and back, keeping her butt pushed down on my pelvic bone as much as she could. As such, I couldn't really thrust much, perhaps an inch or so. No matter, it felt great. She took the weight off of her hands and sat up straight. As such I could gently squeeze and pinch her tits. With her hands free she put her hands on mine and pinched and squeezed along with me. Hot. Very hot.

We carried on a while longer until it was clear that I wouldn't last much longer. I had no idea how many orgasms Robyn had or if she came at all. This was all very new to both of us. I announced, "I'm cumming." and I proceeded to do so. I thrust up hard once, I came and then fell back, spent. She stopped moving a bit later and simply collapsed onto my body, both of us breathing heavily and not moving much.

"Matt, you won't believe how great that was. I felt an orgasm in two or three different spots and each one was different. And after a while, they just flowed. Never ending. Never felt that with butt sex before. This 'cowgirl' stuff must be some powerful juju. I loved it. I think we'll so it again." She dropped her head on my shoulder like she wanted to fall asleep.

I wanted to check on Doug and Marian, so I slipped out from under Robyn and got up from the bed. She moaned and then her head dropped back down onto the pillow, and she was out.

In the living room, Marian was sitting by herself, Doug nowhere in sight. "Did Doug leave already?" I asked. "I'd hoped we could chat about this evening a bit."

Marian patted the seat next to her and I sat down. "I don't think Doug is up for this life we're living. When Robyn blew him, he was just happy for the blowjob. The fact that she is my daughter hadn't quite sunk in yet. At dinner, we were all so OK with that and pleased that Robyn had taken another step in her development, he just went along with the flow."

"So what changed?"

Marian shook her head. "Here's what I think. He told me he's never had butt sex before, and the idea of anal for the first time, with me, was more than he could resist. He couldn't believe that while he was eating me out, my daughter sat down next to me and his friend ate her out. When we left you guys, he wanted to make his excuses and leave. But then, I offered him anal again. I think he knew he would never see us again; indeed, he didn't really want to. So, what the fuck. One butt fuck and out the door. Easy."

I chuckled. "Do a fuck and run. I've been there."

Marian nodded. "You got it. But then you guys started in the room next door. Do you have any idea how much noise you were making? Do you"

I admitted that I had no idea.

"When he realized what you two were doing next door his pecker shriveled up like boiled cabbage. He told me, 'I can't do this. You guys are too far gone. I'm outta here.' And he left. I was disappointed but, hell, I guess he wasn't ready for my ass." Marian burst out laughing.

I shook my head and chuckled. "I wonder how he'll be the next time I see him."

Still laughing, she said, "I wonder if he'll still be in town."

"Who knows? But that does leave us something to think about." I got serious. "We love our unconventional life. But how many people do you think can cope with the 'fuck buddy' lifestyle? Who could understand that you can go out tomorrow and enjoy a rousing fuck with someone you just met, having fucked me the day before and your daughter the day before that? And likely I'll be fucking your daughter while you're with him? It would be hard for anyone to understand."

She said, "Yeah, you're right. We'll need to be way more careful screening the folks we let into our lives. C'est la vie. But that's it. I'm pooped. Shall we hit the hay?"

"Best idea I've heard all day."