Trailer Trash

"That feels nice. I like your touch. It's been so long since anyone has touched me." Karen said.

"They are magnificent. You are a lucky girl." I stammered out.

"Could I lay down and you play with them some more and suck my nipples? I also like it when they are kissed."

"Sure. I'd be happy to." I replied.

Karen backed away and took another long pull on her beer before putting it back on the dresser. She surprised me when she kicked off her shoes, undid her shorts and slid them and her panties to the floor and stepping out of them. She threw herself on the bed resting her head on the pillow and placing her hands above her head. I lay on my side next to her with my head tit high. My hand began exploring the further breast and my tongue began too tweak the closer nipple. Karen immediately groaned with pleasure.

"Oh, that feels so good. Don't stop."

I kept playing, experimenting with different techniques. Karen reacted positively to each one. After several minutes I heard a buzzing sound. Raising my head I saw a long pink vibrator in her hand which she was touching her clitoris.

"I really need to get off. I haven't been with anyone in five months." Karen said.

"I can help with that." I said.

I left her breasts and moved to get in-between her legs but Karen cried out, "NO!" and used both her hands to cover her vagina.

"What's the matter?"

"I haven't done any clean up down there in months. It's a big hairy mess."

Chuckling I said, "Relax Karen, I'm a few years older than you. I didn't lick my first shaved pussy until I was almost 30. It's nice to see hair. Shaved they all look the same, hair gives it character."

Moving into position I moved Karen's hands to the side. Sliding my arms under her legs I lifted and separated them with the intention of getting more playtime with those magnificent tits. Sticking my nose into her full bush (complete with spreading onto the legs) I took a full deep breath catching all of her aroma. There was a little mustiness to her that I didn't mind a bit. Using the tip of my nose I felt around and located her clit nudging it a bit. Karen reached down and pulled her lips open. They were glistening with moisture. She really was turned on. I licked her from the bottom of her slit to the top slowly and when I reached her fun button I stayed in place and vibrated side to side for a few seconds. Her knees and shoulders lifted off the bed for a few seconds before slamming back down as Karen lifted her pelvis a few inches.

"OH GOD DAMN! SHIT!" she cried out.

I took that as a good sign and continued to concentrate on her clitoris using different techniques of licking, blowing and sucking bring her to orgasm over and over again while plying with her tits and rolling her nips between my fingers.

After about fifteen minutes Karen cried out, "Stop, stop, stop. I can't breathe."

I backed off resting my head on Karen's thigh as she just flattened out breathing hard.

"Fuck me. I can't remember the last time I came so much. You are the tongue master." Karen said after a moment.

"I'm glad I was able to please you as much as you did me."

"Yeah, now the ball is back in my court. I gotta up my game on you." Karen replied.

"You don't gotta do anything. You promised a BJ and you gave a great one. This was my thank you. You can relax, I'll let myself out." I responded.

Karen raised her head slightly saying, "You don't want to fuck me?"

"I didn't know that was an option until just now."

"I didn't either but after learning what you can do with your tongue I want to see what you can do with your cock." Karen grinned weekly.

I disconnected myself from Karen and sat up. I still had my shoes and shirt on plus my pants around my ankles. I got undressed and sat on the bed next to Karen.

Karen smiled, "That should make things easier. Listen, I want to do something with you that I haven't done in a long, long time. But I need to know if you get all freaky if a woman gets near your butt?"

"No. I enjoy some butt play. Tongues and fingers, yes. A softball bat, no." I explained.

Karen laughed, "You are really fun. I'm glad I took a leap of faith and took a ride from you."

"I am too. Seriously, I've had a lot of head in my years but that was definitely a memorable blow job."

"Thanks, I'd glad I still remembered how to do it. I haven't had much practice lately. Not to be a killjoy but you need to wear a rubber. I stopped taking the pill a couple months ago. There hasn't been the need to take one." Karen said.

"Yes, you said five months. Why such a long stretch? I mean you seem like such a sexual person. I don't mean slutish. I mean that you enjoy the experience and would want it regularly. Plus, you're very good at it." I smiled.

"Yeah, I have done the slut thing in the past. I jumped on anyone that asked. Even tried a couple of women but that wasn't my thing. Now I'm more selective. It's not worth the drama just to get laid. I get by on my own just fine but I do go thought a lot of batteries." Karen grinned waiving her pink toy at me and slipping it back under her pillow.

"I don't have any condoms with me. I didn't have a clue that I'd be needing any."

"There should be some in the night stand drawer." Karen replied.

I got up and looked in the drawer she gestured at. On the bottom were several different brands of prophylactics strewn about. Some singles, some still attached in strips. However, all seemed to have one thing in common, they were all for large cocks. I don't require that size and have never used one before so I didn't know if it would work on an average man. Would it slide off? I pushed aside a few toys, mostly oversized dildos and didn't find any other size. I picked one that I thought had the best chance of being more towards the moderate size to give it a try.

"Leave that on the night stand and kneel on the side of the bed with your feet hanging off the edge." Karen said as she climbed off the other side and walked around to me.

Karen wrangled me into position with my knees on the bed near the edge and on my elbows. She kneeled on the floor right behind me and placed her hands on my ass cheeks. Tentatively she tongued my taint to gauge my reaction. After my encouraging her to continue she teased my sphincter with her tongue causing a good deal of pleasure for me. My twitching dick caught Karen's attention so she took it in her hand and began milking it like a cow teat. I was enjoying the hell out of this when she upped the game again. Abandoning my butt hole Karen bent my now hard prick back towards her and pulled it in her mouth. She'd suck me for a minute and then return to my anus for some more tongue time and jerking me. Back and forth she worked me over getting me to my 'I must fuck something very soon stage'. Before I had a chance to express my desire Karen released me and stood up.

"Get that rubber on and get inside of me!" she said a little too loudly.

I stood up and Karen took my place on the bed on her back with her legs wide apart. The condom was opened and rolled on. It wasn't as snug a fit as I was used to but snug enough to do the job. Moving to a kneeling position between Karen's thighs I hit a major quandary. I'm not a fan of smokers and definitely don't want to be kissing one. Missionary would put our mouths too close together for my comfort and I didn't want to be that intimate with this woman. To me, kissing is highly intimate and I only kiss women I am in a relationship with besides the casual kiss on the cheek with friends. Instantly it came to me. Taking her ankles I lifted her legs up on my shoulders and lined up my prick for entry. This and her belly would create enough of a lip buffer zone.

"Oh! I never started like this before! Do me stud!!!" Karen called out.

I pressed the head of my cock into her hairy lips finding the right place to be. As my head entered Karen lay on her back, eyes wide open staring at the ceiling. No reaction. Pushed in a bit more into her wet twat. No reaction. A quick push and I was half way in. No reaction. I gave a hard slam. All I heard was a slight 'oh' when my balls slapped against her ass cheeks. I waited a few seconds to see what might happen but there was nothing. Easing back I began long, slow thrusting and to test how the condom was working out. Everything was in order so far.

"Are you all right? I asked.

"Yes, I'm fine. I like this."

Picking up the pace and strength I actually got Karen to move a bit. She shifted herself and began rocking her hips to move with me. After a little more humping she closed her eyes and rolled her head side to side. Her hands reached up and pulled her legs a few inches closer to her chest which changed my angle of entry. Almost immediately it hit her hard.

"OH GOD DAMN! SHIT!" she cried out.

Her whole body quivered from a massive orgasm. She turned her head to the side and relaxed. I slowed my pumping to give her a moment to ride the orgasm wave. Quickly she turned back to face me eyes wide open.

"On no! Don't you fucking stop fucking me. Not yet. You're hitting the right spot." She said with conviction.

Returning to my prior pace I led Karen to four more orgasms but each took a little longer to arrive. With all the energy I was using I needed to slow down and catch my breath. Karen looked up at me with a bit of drool on the corner of her mouth.

"Do me from behind. I like it like that." Karen said.

We separated and Karen turned over. I took the time to check the status of the rubber but all systems were go. Karen was up on her knees in front of me resting on her elbows. Preparing to mount I took hold of her hips. She reached up between her legs and guided me into position. This is always my go to position to get off with, particularly with the big butted women I prefer. While Karen didn't have a big soft ass she did have another good feature. Her love handles/muffin top did make great handles. No more pleasantries, one hard thrust and I was in like Flynn. That did earn me a good grunt of satisfaction from Karen. I pumped away bringing Karen few more overly loud orgasms until she suddenly stopped.

"Hey, do you do anal?" She asked.

"What do you mean? Do I fuck women's asses?" I asked to clarify.

"Yeah."

"Yes I do." I said.

"Do you wanna fuck mine?"

"If you'd like me to. Do you have any lube?" I asked.

"Lube?"

"Yes, lube. I saw some massage oil in the drawer with the condoms but no lubrication." I explained.

"Wait a minute. Let me up."

Karen got up and walked down the hallway. In a moment she returned with a tube of KY jelly.

"Will this work?"

"That's fine."

"Good. One of my sons gets backup up once in a while and I have to use this when I give him an enema."

Wow, way too much information.

"So, how do you want me?" Karen asked.

"Lay on your belly flat on the bed."

Karen took the position and cuddled with a pillow under her chin. I lubed up my cock and then massaged more into her sphincter. Once we were ready to go I assumed the position and held the head of my prick against the tiny muscle. Using steady pressure I worked my way inside her tight ass. Karen groaned into the pillow and wiggled her ass side to side which I look as 'give me more'. Once balls deep I put my hands on the mattress on either side of her and began using long, slow strokes. On each thrust inside Karen gave a 'oh'. As we continued she became more vocal and began to lift her hips to meet me.

"Karen, I am close." I said.

"Go! Cum in me or if you want pull out and cum on me."

A couple more thrusts and I pumped my load into Karen's as cavity.

"I can feel it! I can feel your cum inside my ass!" Karen cried out.

Once I finished unloading I carefully withdrew making sure to take the condom with me. Once out and on my knees I removed the full rubber.

"Let me see it!" Karen squealed.

I held up the device allowing Karen to see the semen pooled in the reservoir tip.

"Shit. If felt like so much more when it was inside of me."

"Has anyone cum in your butt before?" I asked.

"No."

"Why not?" I asked.

"I'll tell you but I want to do it in a way so I will not get you upset. Try to not freak out. OK?"

I didn't like where this was heading.

"I'll try."

"I have tried to get my ass fucked lots of other times but it's never worked out. Sometimes a guy get inside but it hurts too much and he has to get out. I have tried and tried but it never worked. One time my boyfriend and me went to a motel at the shore for a long weekend in the winter when there was no one around and nothing to do and we tried it over and over. We'd try and stop. A while later try again. After when must have been 30 tries we gave up."

"Were you using lube?" I asked.

"Yeah, he got this stuff called Anal Eaze or something."

"Why didn't it work?"

"He was too big for my butt. The head was like the size of an apple."

"Other guys who weren't as big didn't work either?" I asked.

"Well, most of the guys I've been with are about that size. Some bigger and some a little smaller."

"Wow. No wonder you have problems taking it. Wait, so I am the first average size dick you've had?"

"There were a couple others when I was in school."

"So that was the 'ah huh' when you were looking at me for the first time?"

"I was trying to not make a big deal out of it. I know guys can get sensitive about their size. I guess I have just been lucky with well hung guys. I really didn't know there was much of anything else. When I look at porn all the guys are the same size as guys I'm with."

"You do know that they only pick the top sized guys for porn, right?"

"No, I didn't know that. I don't watch much. I'd much rather do it that watch it. But sometimes if I need some incentive as I'm playing with myself I'll watch some. I hope I didn't offend you or nothing."

I pondered that thought for a few seconds and responded, "No, I am what I am. Frankly, I'm about average. I work with what I got. I am not going to get surgery to get longer or thicker, I'd be afraid of losing sensitivity or functionality. I'll stay right here with what I got. So, how did you like anal?"

"It was pretty cool. I like the filled up felling. Next time I want to finger my clit and cum with a cock in my ass. I can't wait to tell my boyfriend that I finally got it."

"Wait? What! Boyfriend?" I stammered out.

"Yeah, don't worry about it. He's serving in Afghanistan for another four months. He knows I get laid. I know he gets laid too but there are not a lot of options over there for American soldiers. I think few of the soldier boys are bending over or sucking some dicks because of the lack of women. They probably run away scared when they see Rogers's dong."

"I don't fool around with women who are taken. Period. If I had known I never would have touched you. Second, I would never disrespect any member of the military like this. I have too much respect for them. I really wish that you would have told me. I feel awful right now."

"Hey, you didn't ask. I didn't ask you either. This is just a little bump and run, no big deal. Don't worry about it. I was actually hoping for a repeat performance. I want more anal now and you licked my slit really great." Karen said.

I really felt disgusted with myself. I wanted to be done with this situation as soon as fucking possible. Getting out of bed I laid the soiled condom on the night stand and searched for my clothes.

"You know, I found it real easy to suck your dick. I could take it all the way down and hold it there with no gag reflex at all. It was really comfortable." Karen explained.

I didn't know if she was baiting me small dick talk or giving me an honest critique of the performance and I didn't care. All I wanted to do is get out, go home and shower.

"Let me give you my cell number. If you change your mind and want to hook up again you can call me." Karen offered.

"No thank you." I regretted saying it as soon as it came out of my mouth.

"Oh? My ass not good enough for you?" She shot out.

I did not reply or look at her. I dressed as quickly as I could and double checked my pockets to make sure I didn't leaving anything behind. Hopefully I would not have to return here.

Karen got up and sat back down at the kitchen table immediately lighting a cigarette and preparing another bong hit.

Once I was ready I moved down the hall quickly and put my hand on the door knob just as Karen fired up the water pipe.

"Karen, tell your boyfriend that I sincerely apologize and I meant him no disrespect."

Karen choked on her hit and I opened the door stepping outside.

"Bullshit! Take your little dick home old man." She cried out before I could get the door closed.

I was very upset about this turn of events. I'd like to think that most people follow the same moral compass that I do but I know it's unrealistic to expect that to happen. If I was in a relationship I would not play around with others and I'd let the other person know right up front. Just like if I had an STD I'd inform my partner.

My take away from this situation is to always ask, don't assume. What makes matters worse is that it affected a soldier. I have the greatest respect for anyone who has or is serving in any of the armed forces. My diddling this soldier's girlfriend, even with his permission or knowledge, is unacceptable behavior in my book and he should have been treated with much more respect than I gave him. Given the opportunity I'd apologize face to face with him and even give him a free shot to throw a punch. I'd hope the apology would be enough since I'm not a fighter but I do owe him one.

I was in the car and moving as quickly as possible. I found my way out of the trailer park by backtracking the route we took to Karen's trailer. Once out I had to get the GPS going to find my way home since I'd never been in this part of the county. I didn't even know what town I was in.

On the drive home I lamented over the pros and cons of the meeting. Karen gave some great and inventive head, was an open and giving lover, an outstanding set of tits and I took her anal cherry. But there were a lot of negatives about her even without factoring in her boyfriend. I took him out of the equation and computed if I'd call her again and decided that I wouldn't, not even as a friend with benefits or a fuck buddy. The negatives outweighed the positives. Live and learn, even at my age.