Let me tell you about my infatuation with my paper carrier. Before you start to think of me as some sort of pervert (which I may very well be) my carrier is not a young girl or boy. She is a very attractive woman in her early 40’s. I’ve known her for a number of years, even before she delivered the paper. Janet is very friendly and will always stop and talk for a minute on her route. A couple of times I asked her in and she would sit and visit. Every time she would come in however, my dick would get hard as a rock and I would look like a klutz trying to hide it.
One day, a few weeks back I asked her to stop back when she was done with her route so I could pay her. I was surprised that she said she would, figuring that she would just say to leave it out for the next day. I was, for the next half hour figuring out how I was going to get into her drawers. On that day she must have come right from her regular job to her route because she was dressed in a skirt and blouse. I asked her in and asked her to have a seat while I looked for the check. She sat down, crossed her legs and her skirt rode up high above her knee. I found the check and when I turned to face her I could see far enough up her skirt to notice that she had on stockings and garters.
I kept staring to see if I could see if she was wearing panties but couldn’t tell. It didn’t make any difference though because by then I was standing there, holding the check, staring up her skirt and sporting a huge woody, and this time there was no hiding it. She said “Is that for me?” “Huh” I said, thinking she was referring to my cock. “Is that check, for me?” this time glancing at the front of my jeans where my dick was making a tent. “Yes, they.. I mean IT is!” handing her the check She smiled thanked me and said that she better get going. Being the wizard I am with women, I mumbled something and watched her go. I decided that it would never come to pass that she would be interested in an affair with a middle aged fat guy so I resolved myself to the fact that I’d only have her while whacking off.
Then the other day she was delivering the paper in the rain wearing a white pullover top and jean skirt. Running from the car to doorsteps along her route, caused the top to get wet and somewhat transparent. I happened to be by the door (really!) when she dropped the paper off and I said something inane about it raining all the while staring at her tits. She smiled, handed me the paper turned to go back to the car, and out of my mouth came “Why don’t you stop by when your done and I’ll dry you off!!!!!!!!” She stopped cold, turned back and looked at me. I figured I ‘d stepped over the line, “Did I say that out loud” I asked rhetorically. Janet smiled and ran through the rain to her car.
I was so upset about what I blurted out the I didn’t even bother to watch her tight ass and bouncing tits as she ran. I’m thinking what if she tells my wife what I said, or her husband, “I’m fucked” I thought as I a got a beer and sat down to contemplate my foolishness. About 30 minutes later there is a knock at the door and when I open it Janet is standing there, still wet, still wearing the see thru top and very prominent nipples staring me right in the face. “Well, are you going to leave me standing out here in the rain, or are you going to ask me in.?” “Come in please” I said. “I’m glad you came back because I wanted to explain my stupid rem….” “Didn’t you say something about drying me off” Janet interrupted as she walked into the kitchen.
I apparently wasn’t catching on because I again tried to explain. “Listen, about what I said” at this point I glanced at her tits and it hit me. When she was here earlier, her top was wet and transparent but she definitely had a bra on. Now I could clearly see the stiff nipples of her now braless tits. “Drying me off?” she said again. OK I don’t have to get hit with a ton of bricks all the time. I went and got a towel and began drying her face and neck. I moved to her shoulders and back and suggested getting her a robe to put on so she could put her top and skirt in the dryer. “How would I explain dry skirt and top and wet bra and panties to my husband?” she asked.
With that she pulled the top over her head and while I stared at her tits and hard nipples, she continued “I took them off in the car” and she slowly raised her skirt to show me her smooth shaven pussy. I took the towel and began to rub it over her tits and her nipples became even stiffer. “Any other wet spots?” I asked. “Just one, but I don’t think the towel will dry it” She moved up to me and kissed, using a lot of tongue. She then slid her hand down and curled her fingers around my cock which by this time was busting my jeans (again). “Does this need drying?” “No” I said, “It needs wetting” pushing her down to her knees. “I’ll start wetting it with my mouth” she said, “but we can’t take long because I need to get home.”
I didn’t argue as she unzipped my jeans, reached in and pulled my hard cock out. “Oh my God, your huge” she said as she rubbed the head of my cock around her face. I didn’t think I was huge but I guess I was to her because she kept telling me how big I was while she was licking it. She put the head of my cock in her mouth and started to slid her lips down its length. She got about half way down and started to choke. “I want it all in my mouth” she cried as she jammed her throat on it again. I was really enjoying this but I knew she would not be able to take it all in. I stopped her and told her it was OK. She said “I’m not very good at giving blow jobs I guess”. “We can work on that another time, right now I want to fuck you”.
She stood up, turned around and stuck her ass out at me. “Fuck me hard and quick, I have to leave soon”. I put my cock at the entrance of her very wet pussy and with one stroke shoved it all the way to the balls. “OHHHHHHHHH MY GOD!!!!” she screamed again. “FUCK ME……………FUCK ME…………FUCK ME”. I did, each thrust lifting her off her feet. After about 4 or 5 minutes she screamed “I’M GOING TO CUM……………….I’M GOING TO CUM………OH MY GOD……….GOD…..I’m CUMMINNNNGGGGGGG!!!!!!” (Its amazing how people get religion when they have sex isn’t it?) In the mean time I’m replaying the 1986 world series in my mind to keep from coming first but that’s not working and I can feel it building up. “Janet, I’m going to cum” I panted. “In my mouth, in my mouth, or on my face or all over my tits……anywhere, just please, not in my pussy” she pleaded. Any one of the options seemed great to me, so I pulled my cock from her dripping pussy, pushed her back down to her knees and shoved my cock in her mouth.
The first stroke went past the high water mark from the last time it was in her mouth and she started to gag. Nothing fucks up an orgasm faster that a gag so I pulled out as I started to cum. My first blast hit her right on the upper lip, second on her cheek and the third……. well, I’m 56 years old, there was no third, but the 1st two really looked good, dripping off her chin and down onto her left nipple. I was leaning over with my hands on the drain board breathing hard and looking at my cum dripping off her. She took my softening cock in her mouth and sucked it clean. “I need to get going but I might need you to help me learn how to suck cock better,. “Well I’ve never done it myself” I said, “but your welcome to practice on my dick anytime you like, if that’s what you mean.”
For the next couple of week s when she would deliver the paper I’d be sometimes waiting by the door to give her tits a squeeze or her pussy a rub. Occasionally I’d have my cock out and in my hand and she would slid her lips over it briefly. Once, I’d been jacking off while watching her deliver around the neighborhood so by the time she showed at my door I was so cranked up that I blasted a load of cum all over her face as she leaned over to give it a lick. At first she was pissed, then she giggled and rubbed her face on the front of my shirt, knowing I’d have to change before anyone saw me. I noticed that there was still some cum on her cheek, I hope she saw it before anyone else saw her!.
This went on for a number of weeks before we decided that we needed to take this affair (such as it was at the time.) a bit farther. I had to go to Chicagoland on business and planned on being there for a day or three, so I asked if there was any way she could meet me there. A couple of days later she told me she could manage to get away for 2 days during that time. I thought “This will work out, it will give me a day to get my business taken care of and 2 days to fuck Janet.” I had to drive but managed to get her a plane ticket and told her I would pick her up at O’hare. I also told her how hot she looked that day I saw her with the nylons and garter belt. I said “I was trying to see if I could see your pussy that day or if you had panties on and this is a not to subtle hint about what I’d like to see you wear” She laughed and said “I’ll see what I can do.”
The first day there I was trying to get work done but had a hard time doing it, no pun intended. That evening by the time I parked at the airport I was sporting some serious wood! I was at he gate when the plane arrived and when I met her she came up and gave me a mouthful of tongue as she pressed he body against me. She said “Just a sec, I want to watch these 2 guys get off the plane”. I didn’t know what she meant but in a minute the last 2 passengers, these 2 guys, got off with the flight attendants following right behind them laughing. Both guys were holding their briefcases in front of them like they were hiding something. When we got in the car, Janet said “You know those seats on Southwest that face each other?” “Yea” I said.
“Well those two men were sitting across from me” as she was telling me this she slid her skirt up nearly to here crotch. She had on flesh colored nylons and garters and when she pulled her skirt up farther I could see why those guys were hiding the front of their pants because she had on a pair of very shear panties and her pussy was clearly visible. “Is that what their view was on the plane?” I asked. “Yea, and when the younger one tried hitting on me, I told them that you were meeting me at the gate and as a cop could carry a gun in the airport, so he left me alone and all he could do was look (No, I’m not a cop and I don’t carry a gun in airports!). It made me so horny that I had to go to the bathroom and rub my pussy.. and all I want to do now is suck your cock!” With that she reached over and unzipped my pants and proceeded to blow me. Even though she needed work on BJ’s I was so worked up that in about 2 minutes I blasted a load in her mouth and this time she swallowed it all.
I managed to get to the hotel without killing us and we started up to the room. In the elevator she dropped to her knees and started to unzip my pants again (Yes, the elevator was empty.) . We only had 14 floors to travel so I hauled her up, hiked up her skirt and began mauling her pussy through her sheer panties. By the time the door opened her panties and my hand were soaked from her sopping wet pussy. There was 2 guys and a couple waiting to get on as we exited and I knew that they had to have noticed the smell of pussy in the elevator but by then the door was closed and we were almost to my room. When we went inside, I asked her if she wanted anything to eat or drink and she said “Yes, your cock and your cum”.
The outside wall of the hotel room was glass from floor to ceiling, so I went an sat in the chair facing the outside wall and said, “Go over there in front of the glass and take off you blouse.” She walked over, stood in front of the glass wall and began to quickly unbutton her blouse. “No, do it slowly like you’re teasing someone watching from the other building” I said while turning on a lamp bathing the window with low light. She looked shocked and turned to look out the window. There was no one that she (or I ) could see watching so she turned back around. I thought I noticed a somewhat disappointed look on her face. “mmm…… I wonder if she would like to show off” I thought to my self.
“Go ahead and get your blouse off.” Janet turned toward the window and slowly opened her blouse exposing her small breasts to all of downtown Chicago. “Push your tits up against the window baby” I whispered to her as I took my cock out of my pants. She pressed her upper body against the window and began unzipping her skirt. “Yea baby, that’s it, show the whole world your hot body” I croaked, barely able to speak. She gasped when I said that and let her skirt fall to the floor. “What do you want now Janet?” I asked. “Please come over here a fuck me” She whispered. I stood up and finished getting undressed. I walked over to her with my cock bobbing around in front of me. She looked so incredible sexy with her tits pressed up against the glass and her shear panty covered ass sticking out toward me. And those nylons!!! God those things turn me on!
I went up to her and wrapped my arm around the front of her and grasped her tits. This was the first time we have been naked together and the first time we were going to be able to take our time fucking. I rubbed my cock against her panty covered ass and pinched her nipples. “Oh God” She cried, “I want your cock in me…right here in the window!” “I hope you didn’t pay too much for these panties” I said. “Why?” she asked. Instead of answering her I reached down and grabbed the crotch of her panties and ripped them away from her. “OHHHHHH……” she cried, and stuck her ass out toward me more. I grabbed a hold of my cock and placed it against the lips of her pussy and rammed it in all the way to my balls. That caused her whole body to be pressed up against the window from her cheek to her knees. “OHHHHH………….GOD…FUCK ME WITH YOUR BIG COCK……..” I knew I’d be able go for a while since she sucked me off on the way over so I settled into a steady rhythm.
Her naked body was slapping against the window like we were laying on a vertical glass bed “Oh Ricky” (that was the first time I heard that from her!) “Baby, keep fucking me…keep fucking me and make me cum….Make me cum then fuck me in my ass!!” Oh shit, I thought, now I have to start thinking about sports again! The way the building was designed some of the rooms down the curved hallway had the exterior windows placed so you could see the windows of other rooms, but I assumed that since it all appeared to be reflective glass you could not really see inside.
As I was hammering Janet’s sopping pussy I noticed a light come on in one of the adjacent rooms. The same light I turned on when Janet started stripping by our window. A women was very clearly visible, standing in her window and was staring at us fucking. I just stared back as I fucked thinking “It must be like lying under a glass bed watching someone fuck” Janet didn’t notice because her face was pointing the opposite direction. The women put her hand under her skirt, smiled and turn her light back off. “Damn” I thought “she just wanted to let us know she could see us” Noticing her distracted me somewhat but now fucking Janet and knowing that this other person was watching got me going again. Janet was about to cum so I picked up the pace as much as I could. “OH BABY…YES..JUST LIKE THAT…..OHHHH GOD I’M CUUUUUMMMMMIIIIINNNNNGGGGGG!!!!!!!!!”
She started to collapse against the window so I reached around grabbed her tits and none to gently pushed her over the small table by the window. I took my cock in my hand rubbed it around her pussy and then up to her asshole. Janet was still coming down from her orgasm and didn’t catch on right away. “Remember saying anything about me fucking your ass?” I asked. Her head came up, “Yes…No…I’m not sure…..WAIT A MINUTE!!!!” Well, I had a woman wearing nothing but nylons stockings, garter belt and a ripped pair of panties hanging off her ass lying over a table in front of me, I had another woman watching from 20 feet away… well… there was no waiting, I put the head of my cock against her asshole and shoved and as I did I reached over and turned off the light.
“OOOHHHHHHH NOOOOOOOO…….” She screamed. “Please stop…. You’re too big…..OOHH GOD YOU’RE RIIPING ME IN TWO” Well, that made me stop. I felt bad about hurting her this way and started to pull my cock out of her ass. “What are you doing…” She screamed “Don’t stop now, keep fucking me in my ass!!!” Damn!! I’m confused but I drove my dick back up her ass and started pumping away. “I’M GOING TO CUM AGAIN…….OH GOD I’M GOING TO CUM WITH YOUR BIG COCK FUCKING MY ASS………..I’M CUUMMIINNGG…. I’M CUUUMMMMIINNNNGGG!!!!!!” I could feel my balls about to erupt so I drove my cock all the way up her ass and unloaded. After a minute I collapsed over her then pulled her down to the floor and held her. She looked up and just smiled. I told her about the woman watching us fuck and how I turned the light off just as I started to fuck her ass. At first she seemed shocked, then intrigued. She asked “What did she look like???” I thought “Oh boy here we go!!!!”
A little later after we showered (together) we decided to go down to the hotel bar for a drink. “What would you like me to wear” Janet asked opening up her suitcase and pointing to the contents. I looked in and it was full of sexy underwear and sleepwear. “I can safely assume I can start with these” she said holding up a pair of black seamed stockings and a lacy black garter belt. “Oh Yea” I said. I held up a black half bra and another pair of shear black panties. “You want me to wear panties?, I’m surprised” she quipped as she pulled on the stockings.
God she looked hot straightening out the seams and smoothing the stockings over he legs. I watched as she hooked the garter belt on then connected the stockings to the garters. I handed her the bra and she put it on saying “My tits are so small, I don’t need to wear this.” She was right, however when she got it in place, her tits were pushed up and together and her nipples stuck out over the half cup. “You sure you want me to wear panties?” she asked again. “Yup” I said, “I’m thinking about having you take them off in the bar!” She didn’t say anything but she looked at me with smoldering eyes and a sharp intake of breath.
I could also see her nipples hardening up and sticking out. She recovered and slipped on a light summer dress that came to just above her knees. She looked hot!!! “My turn” she said. I said “What do you mean your turn” I asked. “I’m going to pick out something for you to wear”. She went over to the closet and got the slacks that I wore to work that day and a casual shirt to go with it. I took off the jeans I pulled on after showering and reached for some underwear. “Oh no, no underwear for you, not tonight!” OK I thought, I’ll go along with this after all were just going down to the bar probably just long enough to get turned on by each other then come back up a fuck for the rest of the night. I pulled the slacks and shirt on, slipped on a pair of sneakers then did the obligatory ½ hour wait for her to finish primping.
When we arrived down at the bar it was only about 1/3 full of the usual midweek business patrons, which I’m usually one of. We went to a booth near the back but not all the way. One, I didn’t want it to look to obvious that we were going to fool around and two, I wanted to show her off. A couple of guys were checking us (her) out as we came in. As we approached the booth I whispered “Show some leg as you slid in” She giggled and as she slid around the circular type booth I could see her dress ride up to her panties. One of the guys at the bar knocked his beer over getting his buddy attention. “Boy, when you show leg you really show leg” I said. She giggled again and we sat side by side facing out into the bar.
After a couple of drinks She asked “When do you want me to take my panties off?” “No time like the present” I replied. “OK excuse me, I’ll go to the Ladies room”. “No way” I said “I want to see you remove them right here at the table. The table area was lower than the bar area so people at the bar could not see under the table but people at other tables could. She looked around and noticed that the few people, two women at one table and two guys at another were not paying attention. Pulled her skirt up lifted her hips and pulled her panties down around her thighs before sitting back down again. She slipped her panties the rest of the way off her legs and got them caught up in her heels.
She kicked at them trying to get them unhooked and apparently they weren’t as caught as she thought because when she kicked they flew out from under the table and landed about 5 feet away. I started laughing and she said “Go get them before the waitress comes back!”. “OK” I said and went out to scoop them up. Neither of the guys noticed but the one woman who was facing our direction did, and was telling her friend about it. By this time I’m back at the table. Janet giggled and said “I could see your cock flopping around in your pants when you went out there.” Apparently so could this other woman because she was starring at the front of my pants where my semi hard on was lying along my leg.
Janet saw the woman looking and reached over and started squeezing my cock through my pants. I could see her telling her friend what Janet was doing. I could not see what her friends reaction was. After a little bit the woman I could see, got up and with a smile in our direction left the bar. The two guys had left earlier so I saw this as a chance to play with Janet’s pussy and tits. I had her dress front pulled down over her shoulder exposing one nipple and my hand up under the hem of her dress rubbing her pussy when I noticed the waitress approaching. She was carrying two more drinks that I didn’t order.
I got Janet’s dress up but my other hand was still on her pussy and my middle finger was staring to slid in and out. As she set the drinks down and before I could ay anything about not ordering any she said “The lady at the other table sent these drinks with her compliments and this note. I pulled my hand out of Janet’s pussy to get the note. I know she could smell pussy on my hand as she handed it to me. She left and I opened the note. It said “You guys look like you’re having as much fun now as you did earlier in the evening in the window.” It was the women in the window watching us. I looked over at the table and saw who initially had her back to us, turn around and raise her glass in toast
. Janet asked what was going on. I showed her the note. She gasped, looked at the woman, hesitated, then turned to me and said “Why don’t you go ask her to join us”. “Are you sure” I asked?. “Yes, hurry before she leaves or I lose my nerve.”. I walked over to her table and said “Thank you for the Drinks” She said “Thank you for the show, or should I say shows.” “I would like to see the end of one of them though.” She went on “The first one, the lights went out and this one most likely will not end here in the bar”. “Would you care to join us” I asked. “I’d love to” She replied. When we got back to the table she motioned me in first then slid in behind me so I was between the two of them. She reached her hand across me to Janet and said “Hi, I’m Karen”. Janet smiled shook her hand and said “I’m Janet, and this is Rick.”. “Are you two married?” Karen asked.
Before I could answer Janet said “Yes, definitely, but not to each other” and went ahead and explained our little road trip. While she is doing this I’m checking out Karen. She was tall about 5-8 or 5-9 jet black hair (Tied up) and wearing a dark women’s business suit with a white blouse. Definitely a babe. I got back into the conversation as Janet was saying “I’m sorry he turned off the lights when he did, that was a dirty trick.” “I know” Karen answered “Watching you two was better than the porn pay per view I was watching.”
She hesitated then asked “Was he about to do you in the ass or was that a dirty trick as well?” “No” Janet said with that smoldering look that I was getting used to in her eyes again “As soon as the light went off he drove his monster cock straight up my ass” Karen looked at me “I’ve never been fucked in the ass” then she looked at Janet “Monster cock??” Janet took Karen’s hand that was resting on the table and placed it on my ever hardening dick. “Monster” Janet repeated. Karen gasped and said “Good lord, this was in your ass???” By now I’m beginning to think that maybe I do have a big dick. I hear Janet say “ Yup, one thrust and it was all the way in, my first time too….but I was so turned on from fucking against the window that I didn’t feel any pain at all.”
“You really looked hot pressed up against the window like that” Karen said as she reached over and placed her hand on Janet’s breast. Oh boy, I’m thinking I’m going to need to relive the 86 World Series as well as the 99 Stanley Cup tonight. “Why don’t we go to the room?” Janet asked. “You Ladies go ahead” I replied. “I’ll get the bill and besides I can’t really get up and walk at the moment” I continued, pointing down to the tent in my pants. Both women reached over and gave my cock a squeeze and started to get up. “Oh yea, that will help a lot!! I quipped. They laughed and Karen said “We’ll leave you to fix your problem, but whatever will we do while were waiting for you?” she said taking Janet’ hand. “You’ll think of something I’m sure” I said.
The waitress came over o few minutes later and collected the bill. “Enjoy your evening” she smiled as she knowingly walked away. It took about 20 minutes of watching some old golf match on ESPN Classic before I could leave the bar. When I got to the room there was a note and a key on the bed. It was from Janet. It read “Karen has a Suite with a hot tub, meet us up there, don’t bother bringing a suit.” I knew I wasn’t going to get much sleep tonight!