One Night in Chicago
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One Night In Chicago free porn video
Weekend in Chicago! My delicious secret!
Not too long ago, one of my sexy friends asked me if I had a sexual experience that stood out in my mind; one that I’ve never really told anyone. Well…the answer to that is yes! I do, it’s been my little delicious secret for quite a while. Today, I am finally going to share it.
My stepdaughter, Jessie – who is a real cutie – played on the tennis team in college. She told me about all the players on the team but the conversation kept coming back to her roommate, Maria. They hit it off quickly becoming friends from the moment they met. It seemed like they really enjoyed each other’s company and had a blast playing tennis. The team was really good too! When the two girls went out together, Jessie (my stepdaughter’s name) would tell me that there would be a steady stream of guys hitting on them. Who could blame them, slender athletic bodies, and I never remember seeing them with as much as a hair out of place. They were inseparable, did almost everything together. I actually thought to myself that they HAD to be lovers – at least experimented, but to my surprise, I found out later that they never did! But that is another story for another time! I can tell you, every time I saw the two of them together, my dirty mind ALWAYS thought of how hot it would be to watch – or better yet, join in…
One time that stuck out in my mind was when Jessie brought Maria home with her for the weekend. They seemed to have a lot of fun. My wife, Amy loved having them around too. Seems like she might have been thinking similar thoughts that I was having when I saw the two college girls together. Not to divert from the scenario, but when you see mother and daughter together, it’s the most amazing thing you ever saw! Maria and Amy almost look like twins, mom has a few more curves, and fuller tits, but they are both stunning! Not to brag further, but sometimes when people see us walking around in New York, they stop because they say we look famous.
After picking the girls up from college, they hopped out of the car before it fully stopped, and before I knew they were out of their street clothes and in smoking hot looking bikinis! I collected my composure changed into my trunks and joined them out at our pool. Jen called me inside to help with the food, then she ran out to join the girls for a quick splash in the pool too. I brought out the food and decided to spend a little time splashing around in the pool with the three angels before eating. Jen and I got out of the pool first, and she was drying off, she bent down to dry her long hair. Suddenly, I walked up behind her and swatted her wet bottom as hard as I could!!! She was wearing a little bikini and she turned around rubbing her bottom and said… “Ronnie!…OMG what was that for”? I winked at He winked at Maria and said, “her butt was just too damn cute and it looked like it needed to be swatted”. The slap was so hard that it left a handprint on her wet bikini bottom – so just imagine what her ass must have looked like! Jen raised her eyebrows at me and said, “Honey, we have company, remember”? I smirked, and looked again at J, she was blushing and squirming – I knew that she seeing me slap my wife’s ass had really turned her on. I saw Maria staring at my wife rubbing her sore ass. Then I saw her eyes go right to my bulge, which was starting to grow a bit. I hopped back in the pool, hoping to let the cold water shrink my bulge a bit; it didn’t work. When I got out, my trunks were pasted to my body. I had been working out again, so I was getting nice shape to my form. But the trunks were tighter than I thought when I put them on, you could actually see the outline of my cock as clear as if I had on nothing. I’m pretty big “down there”, and I could tell that my wife, my stepdaughter, and her friend all took the time to steal a glance. I wasn’t hard, but the water did nothing except make the outline more noticeable. I wasn’t ashamed, but I definitely didn’t plan to show off my dick at dinner!
Dinner was amazing. Wall all talked and laughed, shared stories and a few bottles of wine. It was getting late, and it had been a fun but very long day. So, the girls went downstairs to Jessie’s room to watch a movie and crash for the night. The wine had gone to our heads and we were already horny, so I made a fire in our pit on the patio and started to romantically enjoy each other by the light of the moon and the fire pit. Didn’t take long for us to get naked, and very very hot. I don’t know how long we had been going at it when I thought I saw a shadow from the kitchen. I was pounded Amy pretty fucking hard, and she was screaming, “fuck me deep, give me all that fucking cock, baby” loud enough that I’m sure the girls could hear us from the house if they were awake. I was slapping her ass so hard that the sound was echoing in the night air, and deep stroking, giving my wife every inch of my cock. Out of the corner of my eye, I noticed Maria, sort of peeking out onto the patio. At first, I continued to go at it, fucking like a****ls, in the open late summer air. I tried to act casually, pretending that Maria couldn’t see me, but I caught her eye, and we stared at each other for a few moments. I flashed a smile to let her know that I was ok with her watching. She smiled but moved into a spot where it was harder to see what she was doing. But I could tell that she had slipped her hand inside her panties, and was rubbing her pussy as she watched us. That turned on so fucking much that I went from nice hard, aggressive sex, to just all out earth shaking, fucking. I looked up every now and then, watching Maria pussy play and started to fuck Amy so hard that at one point she said “not so deep baby”. After a while, I felt to surge, and knew I was about to cum. I looked up one more time, this time I nodded at Maria and she moved into a position where I could actually see her sliding her fingers in and out of her tight, young pussy. She had stepped out of her panties, leaning on the counter I saw her begin to convulse, and that was all I needed to put me over the top as well. I wanted to give Maria a show, let her know that a guy old enough to be her father still had skills. I pulled my cock out of Amy, and showered her with my cum! That made Maria’s knees buckle; she got herself together and ran back downstairs. In the meantime, I took the blindfold off Amy, loosened the restraints, she came again from the force of my cum shower, and wanted more. “Let’s go to the bedroom,” she said breathlessly as she walked away. I couldn’t get Maria out of my mind, so I told Amy to head into the house and get ready for more fucking while I checked in on the girls…
I took a few extra minutes going in to finish off Amy, telling her I wanted to check in on the girls before coming back up to fuck the living daylights out of her. She said ok, so I down to their room and peaked in. Maria was waiting for me. Laying in the bed facing the door, she was quietly shoving her fingers in and out of her pussy. Jessie was sound asleep – the wine might have knocked her out. I stood in the doorway, and pulled out my cock. Maria licked her lips and kept stroking her pussy. She was on her back…legs wide open…fucking herself like nothing I have ever seen. She covered her mouth to try to muffle her moaning. I just watched with my cock in my hand for a while, but then I started stroking. She started to cum…and boy did she ever. Her back arched and she really came hard. It was so sexy. I was trying to hold back, because I needed to get back upstairs to my horny wife, but I couldn’t help myself. It only took a few minutes before I felt my body tighten. I muffled a moan, preparing to blast the girls’ bedroom, but Maria hopped off the bed like a fucking cat, and got on her knees in front of me. She said in the sexiest fucking whisper ever, “shoot my face daddy!” And as she said that, my cock blasted her so hard that her head shot back! She was rubbing her pussy with one hand, and catching the cum dripping from her face in the other hand. She came again, and this time she moaned loud enough that Jessie started to stir from her sleep. I stepped carefully back, watching as she finished licking my creamy cum off her fingers. I could tell by the look on her face that she wanted it to continue, but we agreed without speaking that we didn’t want to take a chance on getting busted…
By the time I got back to the room, Amy was asleep, so I climbed in the bed, drained but still horny. A little while later, Amy woke me up, we cuddled, until I was hard again and then we fucked until we both just passed out to sleep…
The next morning, before we went out into the rest of the house, Amy and I fucked again. We were both so horny, it was like we were k**s again. I fucked her so loud that I know neighbors could here and we are on a nice piece of property! At one point, I was spanking her with my bare hand and the sound was echoing through the house. Between the ass smacks and me pounding her so hard that pussy juice was splashing up my torso, she came hard a few more times. We were pillow talking to each other, and I told her how good her pussy felt. I’m telling you, we were like newlyweds. After a few more minutes or this, I pulled out and we got out of bed, where I turned her around. She slowly bent over, on her knees and elbows and put her face on the bed. I rubbed my long thick throbbing cock between her ass cheeks and gave her another little smack and asked if she was ready. She moaned yes, as I he entered her again. Just as she buried her face into the bed, Maria walked past the room. I didn’t know at the time, but Jessie had gone into town for more food and supplies, and left Maria sleeping. I think hearing her best friend’s parents fucking probably woke her up. So while I was pounding my wife, she tiptoed to the door and was looking in just as I looked up. Our eyes met, I smiled; she blushed, and nodded for her to come in.
I smiled at Maria, pointed over to the closet, and she quietly tiptoed in where she could watch. Amy was still blindfolded, so she couldn’t see a thing. I would slap her ass or pound her extra hard as Maria walked past so that all Amy could think about was the joyful pain I was inflicting. Once Maria sat and closed the door just enough to not be seen, I grabbed Amy’s perfectly curved hips and started fucking her hard and deep all over again. Being watched by a girl I actually wanted to fuck made me so hot I thought I was going to burst. And what made it even hotter was that Amy didn’t have a clue that I was fucking her while thinking about fucking her daughter’s best friend. I was going really deep, when Amy reached back between her legs and squeezed my balls. It didn’t take too much longer until I pulled out, and shot a huge load all over Amy’s back and ass. I was still hard, so I put my cock back inside her and pumped her a few more times before collapsing. I waved my hand for Maria to leave, and I watched her leave. She had cum several times, so her panties were soaked through. Before I took off Amy’s blindfold, I kissed her and decided to take a shower with her. Amy sneaked off quietly, and I heard water running. I knew she could not get back in the bed after cumming that much without a shower. I slipped away quietly and hustled back downstairs to sleeping Maria. I was so turned on thinking about her that I fucked Amy again in the shower, and later, I masturbated thinking about her. At one point, I remember dreaming, thinking about how hot it might be if my daughter was bi. I KNOW my wife is, but imagine my wife, my stepdaughter and her best friend – three hotties fucking each other and me in the middle. I know it’s naughty as fuck, but trust me, I have cum many days with that same dream!
The girls left the next morning. Amy and I were actually just about to fuck when they knocked on the door to say good-bye. We called them over and gave them hugs, I made a point of letting Maria see my hard cock up close before they ran out the room. I knew that Maria would never tell what she saw, and I hoped that one day, I would get the chance to give her what she seemed to want so badly from me…
But here comes the REAL secret… Fast forward 6 years!!!
I was in Chicago, at a medical convention and guess who walks into the hotel lobby??? Maria!!! I recognized her immediately and greeted her warmly. She recognized me and called me by my first name – no more Mr. or “Sir.” I told her why I was in Chicago, and would be staying for a few days. She told me she was travelling for another conference – in a hotel across the street and suggested that if our schedules synced up, that we should get together for dinner. We looked at our calendars, and decide on that night. As she walked away…I thought…”god damn, that woman is sexy!” Much hotter than she was that weekend she spent at our place. She turned back around, as if she could read my thoughts, winked, and that let me know that she remembered our unspoken promised. I was so turned on that I went back to my room and stroked out a nice midday load.
I found it almost impossible to concentrate for the rest of the day. I kept thinking about her. What would she wear? What will we talk about? I reminded myself that this was my stepdaughter’s best friend, but then I said, “she was almost grown then but she is surely grown now!”
After my last workshop, I went to the stylist to get a shave, and got myself in presentable shape to meet this hot young thing that if things would right would fuck my brains out. I went to the lobby, rang her room and told her I was there. I had on a nicely tailored black suit – trying to look as dashing as I could for my hot young companion. She had on a dress that made me hard just watching her walk from the elevator to the desk. I kept my composure long enough to say Maria, You look gorgeous” as I leaned in and kissed her on her cheek. I let the kiss linger as I wrapped my arm around her waist. She purred and began to melt into my arms, but I let her go just before we both forgot and said, “fuck dinner! Let’s go to the room!” I stuck out my arm, which she eagerly accepted, and we stepped into the limo I had waiting outside. We went to a very nice restaurant and had the best time. We talked about everything! It was fun catching up. She told me told him how much she enjoyed the time I spent at their house. We talked about that for a little while. Then she blushed and leaned in a bit and told me in a half-whisper how much she loved when he smacked Amy on the butt. She told me that she also had a little bit of a spanking fetish and found it to be a huge turn on watching me do that. I talked about Amy’s still tight and sexy ass, but then I confessed that Amy and I were going through a few problems and had separated. She could probably feel my sadness when I told her that I wasn’t totally sure if we would ever get back together. She touched my hand and said I’m so sorry Ron, which cheered me up enough to say “on a lighter note, tell me more about this spanking fetish” we laughed, and that and the second bottle of wine lightened the mood enough for Maria to tell me a little bit more. I was rock hard when I finally said…”well, maybe you’ll be naughty enough tonight that I will have to spank you”. She responded…”Ron, I sure hope so!” We had the best time at dinner; we really enjoyed each other’s company. It was very clear that we were both getting very turned on. It wasn’t just the wine – trust me. I would have been throbbing hard for her under any circumstance. I told her how great I thought she looked; she told me that she was glad we were able to connect again.
We left the restaurant and went for a ride in the limo. We enjoyed some of the sights of Chicago and sipped a little more wine. It was very romantic. We felt the connection so at one point, she scooted over next to me, she wrapped her arm around me, put her head on my shoulder. I pulled her a bit closer, and started to softly rub her leg. When I told her how much I enjoyed seeing her again, I leaned in for a polite kiss, she moaned softly, as our lips touched…
We got back to the hotel and I asked her …”well, is there anything else we can do tonight”? She looked up at me and said “Ron, would you like to come up to my room? We can continue our wonderful night”. I almost said, “Absolutely!”. A bit too fast. But I told her I wanted to change out of the suit and get into something more suitable for the next phase of the night. So I trotted across the street, and made a quick change. 10 minutes later, I was knocking on her door…
Maria invited me in, and before I was even fully in the room, I gently drew her to me, and we hugged and kissed. We sat and talked a little while about how much we enjoyed the evening, we sipped a little more wine, and when I told her how incredible she looked in the dress she wore, she surprised me by telling me that she actually wore it just for me – just so I would notice her. I smiled, and leaned back in the chair and said to her in a mocking voice “you are a bad girl Maria”. She looked at me with hungry eyes and said, “yes I am”. I got up and moved over to the bed and said…”you know what happens to bad girls, don’t you”? She smiled, enjoying the sexy banter and said…”What’s that”? “Come over here and I’ll show you”. She came over to the bed, and sat very close to me. In a stern voice, I told her to stand up. I took her hand and said, “now, lay across my lap”. As she did as she was told, I told her to put her my hands under my legs, she did it and looked back at me over her shoulder. I gently pulled her dress up, revealing her little sexy lace panties. I let out a moan when I saw them. Then I rubbed her mostly bare bottom and told her that unfortunately, those tiny panties won’t offer much coverage or protection for the spanking she was about to get. I rubbed her bottom, exploring and smoothing my hand over it thoroughly. I payed special attention to the underside and let my hands and fingers go deep between her legs. I could tell by the warmth, and the wetness, and her soft purrs and moans that she was getting aroused like never before. I told her in my authoritative voice that her perfect little ass needed to be spanked, and gave her a couple of light smacks. She looked back at me – I looked into her beautiful eyes, and said calmly, lift your bottom up. When I got her to do that, I reached between her legs and with my hand wrapped around my pussy, I pulled her up to where I wanted her. I told her, “Maria, spread your legs apart slightly; that’s it honey…now this ensures that you don’t tighten up and I will feel the spanking better. I was really getting hot. Then I said…”Maria, what happens to bad girls”? She said, “they get punished”? I said “be a little more specific.” She said, “they get spanked?” I said “yes, now let’s get going.” I rubbed her perfect ass cheeks until I could feel her total relaxation, then I drew my hand back and “WWWHHHAAACCCKK!” I smacked her ass as hard as I could. She screamed out loudly, a mix between pain and pleasure as she squirmed I rubbed her ass, telling her to hold still, and then…rubbed my ass and told me to hold still…..then……”WWWHHHAAACCCKKK” right across both cheeks! My ass was on fire. He was really spanking me hard. I yelled out…”OUCH”. I reached back to rub my bottom and he told me to put my hands back under his leg. He said “no rubbing”. “Bad girls need to feel the sting”. I told her to raise her bottom and part her legs. I did so… and… “WWWWHHHHAAAACCCKKKK!!!” This one covered the underneath side of my butt. I screamed out….”OUCH”. He then rubbed my little butt that was now on FIRE. He said…”Wow, you’re a tough bad girl aren’t you”? “I love disciplining tough bad girls”. Then, WWWWHHHHAAAACCCCKKKK!!!” She yelled out, “FUCK!!!!! My ass is on fire, Ron!!!” I was a little concerned that I might have hit her too hard, but she was breathing heavily, and moving her ass, making sure that my hand slipped between her cheeks. She said again in a soft, sexy, willowy voice, “My ass is on fire…daddy,” and when she said that, I felt a surge in my cock like never before. My hand went between her legs, and as soon as I sunk my fingers inside her, I could feel her warm wetness completely envelope my fingers. I moaned, “mmmm…what have we here? Feels like someone has a very wet pussy. I will deal with THAT in a minute…” I looked at her ass bright ass, but delicious looking as hell. I moaned as I knelt above her, one hand moving from her pussy to the crack of her as and back again. My other hand was on my cock, which had grown to throbbing. I looked down and said to her, Fuck! Maria, this is exactly how a bad girl’s ass should look! Glowing red and hot.” I let her rub her sore ass, which she did, almost masturbating as she explored the contours of her radiating bottom. I told her to take off the dress, she did so, revealing a gorgeous black see through bra and panties. For me, time for spanking was DONE, I wanted to get my throbbing dick in between those red cheeks, and between those tasty looking pink pussy lips!
I still had my hand on my cock when I turned her around and told her to take off her panties. I had been looking at her from the back most of this time, but seeing her face me, she looked like an absolute angel. She had on a front-snapping bra, so as she stepped closer to me, offering to let me unhook her, those perfectly hand sized natural tits bounced in my face. I put one in my mouth sucked until she moaned again. Then I took a step back. I stepped out of my jeans, and my cock sprung up like a toy. Her eyes widened, and she mouthed the word “wowwwwww,” and started to squirm. That told me that her juicy pussy was dripping and she needed something – like a hungry mouth or a hungry cock to help her out. She looked up at me, leaned in to kiss me, pressing her tits against my chest, then slowly kneeled. She looked up, and said, you are even bigger then I remember, as she began to slowly alternate between kisses and licks on my cock and balls. She gave me the cock sucking of my life! A few times, I reached down to feel her tits, but she pushed my hands away. “Now, it’s my time to take YOU over, sirrrrrrr…” She pushed me back on the bed, licked her way from my balls and cock, up my stomach chest and neck. Then she planted a full-mouthed tongue kiss on me that was better than anyone ever had. She lifted up and said, do you know how many nights I came myself to sleep dreaming about feeling you?” Then she reached back, felt for my rock hard cock and slowly put it in her. She whispered, “fuck, you are almost too big for me…ALMOST!” With that, she inched me inside her little by little, she even had a couple of small orgasms taking me inside. Finally, she sat up straight on my cock, and said, “you’re all in, honey. Now it’s my turn to put a whipping on you!” and she went to work on me…
Even though she was riding me slowly, softly deeply, I was determined to take back control. I said to her in a firm voice, “I’m going to make that pussy feel good Maria” She laughed, and said, “I got this baby. Take this pussy!” Watching her personality change from the demur hot young woman to this tiger in a see through push up bra was as hot as the fucking she was grinding out on top of me. She was grinding and bouncing, rocking her hips, taking my hands to give herself leverage. Her pussy was so wet that juices were flowing down my shaft onto my balls. She told me how big I was compared to her others, to my surprise, I managed to sneak in a couple of nice firm smacks on her ass. This time she didn’t yell; she just bounced higher and harder and said, “smack my ass good daddy!” I saw her facial expressions change, and then she started speeding up. She was moaning, “oh fuck, daddy, you got me good…fuck meeeeeeee!!!” and with that, she started to convulse, she gave a low groan, they she absolutely EXPLODED on my cock! She was bouncing uncontrollably; I felt her pussy tighten on me with each bounce. But by the third one, I felt my cock tighten and I said to her, “I’m right behind you honey…” My whole body started to jerk, and I could feel and hear the spurts of my thick, creamy cum shooting up inside her. But I was still hard so I flipped her over, spread those legs and rammed my cock in her so deep that my balls were making a loud slapping sound against her ass! She wrapped her legs around my ass and said, “I want you as deep in me as you were in Amy that night!” I literally felt my strength and my hard on come fully back. Her pussy was so good, I was fucking the way I was as a teenager.
Maria was taking my cock, looking down at me entering her, the sight of seeing my ramming my cock in and out of her made her cum again. She started kissing me deeply as we fucked. It was the best sex I ever had, and the fact that we had both been fantasizing about each other for the past six years made it even better! I couldn’t take any more. This time, to my complete amazement, I came again, even harder than I did the first time. Maria came again too, then wrapped her legs around me tightly and wouldn’t let me pull out. We laid there in a sexy, romantic sticky heap. It was beautiful, and totally intoxicating.
We showered together and when we did, I made a point of paying special attention to her red stinging bottom. We kissed and made out in the shower. After that, we got dressed and were going to go down to the hotel bar to get a drink. We walked out of her room and the older couple in the neighboring room was coming out of theirs. They had a look on their face…and expression that they knew something. The lady smiled and said…”Hmmm…sounds like someone might have a sore bottom, but it appears that it was quite enjoyable.” We looked at each other and laughed, we were so embarrassed. I looked the elderly woman in the face and winked, saying, “yep, sometimes a bad girl needs a spanking!” She looked at me as if she wanted a little of what I just gave Maria, as the husband continued walking down the hall. The lady said…”well, I used to be a bad girl myself” and she winked at Maria...
We decided to spend the rest of the weekend together. We ended up fucking several more times over the next two days. We spent it basically like a married couple – fucking, ordering room service, taking a swim in the hotel pool, coming back and fucking some more.
Since that amazing weekend, we have managed to keep in contact but that was the last time we ever made love. A year later, I let Maria know that Amy and I got back together. She told me she was happy for us. I said half-jokingly that maybe one day, she could come for a visit, and a threesome. She laughed, and said she might consider that.
By the way, for what it’s worth, Jessie never seemed to be aware that I fucked her best friend from college. She never knew that Maria and I spent a glorious weekend together, or that six years before, that she sat in a closet fingering her pussy watching me fuck her mom into oblivion. Who knows what might happen if she ever found out.
Here is the funny part of the story… Maria called me about a month ago asking me how things were with Jessi. She had been on her mind. Maria confessed that she has had a crush on Jessie since they met, but they never acted on it. I told her that she should tell Jess – it might do some good. She didn’t know that I overheard Jessie telling her mom how she felt. Amy told her to make it known, but not to expect much. Well, long story short, the two angels chatted, and Jessie and Maria confessed their years of unspoken desire. They planned to meet last month, but I have not heard the details. When I hear about that, I will be back with another story!
Not too long ago, one of my sexy friends asked me if I had a sexual experience that stood out in my mind; one that I’ve never really told anyone. Well…the answer to that is yes! I do, it’s been my little delicious secret for quite a while. Today, I am finally going to share it.
My stepdaughter, Jessie – who is a real cutie – played on the tennis team in college. She told me about all the players on the team but the conversation kept coming back to her roommate, Maria. They hit it off quickly becoming friends from the moment they met. It seemed like they really enjoyed each other’s company and had a blast playing tennis. The team was really good too! When the two girls went out together, Jessie (my stepdaughter’s name) would tell me that there would be a steady stream of guys hitting on them. Who could blame them, slender athletic bodies, and I never remember seeing them with as much as a hair out of place. They were inseparable, did almost everything together. I actually thought to myself that they HAD to be lovers – at least experimented, but to my surprise, I found out later that they never did! But that is another story for another time! I can tell you, every time I saw the two of them together, my dirty mind ALWAYS thought of how hot it would be to watch – or better yet, join in…
One time that stuck out in my mind was when Jessie brought Maria home with her for the weekend. They seemed to have a lot of fun. My wife, Amy loved having them around too. Seems like she might have been thinking similar thoughts that I was having when I saw the two college girls together. Not to divert from the scenario, but when you see mother and daughter together, it’s the most amazing thing you ever saw! Maria and Amy almost look like twins, mom has a few more curves, and fuller tits, but they are both stunning! Not to brag further, but sometimes when people see us walking around in New York, they stop because they say we look famous.
After picking the girls up from college, they hopped out of the car before it fully stopped, and before I knew they were out of their street clothes and in smoking hot looking bikinis! I collected my composure changed into my trunks and joined them out at our pool. Jen called me inside to help with the food, then she ran out to join the girls for a quick splash in the pool too. I brought out the food and decided to spend a little time splashing around in the pool with the three angels before eating. Jen and I got out of the pool first, and she was drying off, she bent down to dry her long hair. Suddenly, I walked up behind her and swatted her wet bottom as hard as I could!!! She was wearing a little bikini and she turned around rubbing her bottom and said… “Ronnie!…OMG what was that for”? I winked at He winked at Maria and said, “her butt was just too damn cute and it looked like it needed to be swatted”. The slap was so hard that it left a handprint on her wet bikini bottom – so just imagine what her ass must have looked like! Jen raised her eyebrows at me and said, “Honey, we have company, remember”? I smirked, and looked again at J, she was blushing and squirming – I knew that she seeing me slap my wife’s ass had really turned her on. I saw Maria staring at my wife rubbing her sore ass. Then I saw her eyes go right to my bulge, which was starting to grow a bit. I hopped back in the pool, hoping to let the cold water shrink my bulge a bit; it didn’t work. When I got out, my trunks were pasted to my body. I had been working out again, so I was getting nice shape to my form. But the trunks were tighter than I thought when I put them on, you could actually see the outline of my cock as clear as if I had on nothing. I’m pretty big “down there”, and I could tell that my wife, my stepdaughter, and her friend all took the time to steal a glance. I wasn’t hard, but the water did nothing except make the outline more noticeable. I wasn’t ashamed, but I definitely didn’t plan to show off my dick at dinner!
Dinner was amazing. Wall all talked and laughed, shared stories and a few bottles of wine. It was getting late, and it had been a fun but very long day. So, the girls went downstairs to Jessie’s room to watch a movie and crash for the night. The wine had gone to our heads and we were already horny, so I made a fire in our pit on the patio and started to romantically enjoy each other by the light of the moon and the fire pit. Didn’t take long for us to get naked, and very very hot. I don’t know how long we had been going at it when I thought I saw a shadow from the kitchen. I was pounded Amy pretty fucking hard, and she was screaming, “fuck me deep, give me all that fucking cock, baby” loud enough that I’m sure the girls could hear us from the house if they were awake. I was slapping her ass so hard that the sound was echoing in the night air, and deep stroking, giving my wife every inch of my cock. Out of the corner of my eye, I noticed Maria, sort of peeking out onto the patio. At first, I continued to go at it, fucking like a****ls, in the open late summer air. I tried to act casually, pretending that Maria couldn’t see me, but I caught her eye, and we stared at each other for a few moments. I flashed a smile to let her know that I was ok with her watching. She smiled but moved into a spot where it was harder to see what she was doing. But I could tell that she had slipped her hand inside her panties, and was rubbing her pussy as she watched us. That turned on so fucking much that I went from nice hard, aggressive sex, to just all out earth shaking, fucking. I looked up every now and then, watching Maria pussy play and started to fuck Amy so hard that at one point she said “not so deep baby”. After a while, I felt to surge, and knew I was about to cum. I looked up one more time, this time I nodded at Maria and she moved into a position where I could actually see her sliding her fingers in and out of her tight, young pussy. She had stepped out of her panties, leaning on the counter I saw her begin to convulse, and that was all I needed to put me over the top as well. I wanted to give Maria a show, let her know that a guy old enough to be her father still had skills. I pulled my cock out of Amy, and showered her with my cum! That made Maria’s knees buckle; she got herself together and ran back downstairs. In the meantime, I took the blindfold off Amy, loosened the restraints, she came again from the force of my cum shower, and wanted more. “Let’s go to the bedroom,” she said breathlessly as she walked away. I couldn’t get Maria out of my mind, so I told Amy to head into the house and get ready for more fucking while I checked in on the girls…
I took a few extra minutes going in to finish off Amy, telling her I wanted to check in on the girls before coming back up to fuck the living daylights out of her. She said ok, so I down to their room and peaked in. Maria was waiting for me. Laying in the bed facing the door, she was quietly shoving her fingers in and out of her pussy. Jessie was sound asleep – the wine might have knocked her out. I stood in the doorway, and pulled out my cock. Maria licked her lips and kept stroking her pussy. She was on her back…legs wide open…fucking herself like nothing I have ever seen. She covered her mouth to try to muffle her moaning. I just watched with my cock in my hand for a while, but then I started stroking. She started to cum…and boy did she ever. Her back arched and she really came hard. It was so sexy. I was trying to hold back, because I needed to get back upstairs to my horny wife, but I couldn’t help myself. It only took a few minutes before I felt my body tighten. I muffled a moan, preparing to blast the girls’ bedroom, but Maria hopped off the bed like a fucking cat, and got on her knees in front of me. She said in the sexiest fucking whisper ever, “shoot my face daddy!” And as she said that, my cock blasted her so hard that her head shot back! She was rubbing her pussy with one hand, and catching the cum dripping from her face in the other hand. She came again, and this time she moaned loud enough that Jessie started to stir from her sleep. I stepped carefully back, watching as she finished licking my creamy cum off her fingers. I could tell by the look on her face that she wanted it to continue, but we agreed without speaking that we didn’t want to take a chance on getting busted…
By the time I got back to the room, Amy was asleep, so I climbed in the bed, drained but still horny. A little while later, Amy woke me up, we cuddled, until I was hard again and then we fucked until we both just passed out to sleep…
The next morning, before we went out into the rest of the house, Amy and I fucked again. We were both so horny, it was like we were k**s again. I fucked her so loud that I know neighbors could here and we are on a nice piece of property! At one point, I was spanking her with my bare hand and the sound was echoing through the house. Between the ass smacks and me pounding her so hard that pussy juice was splashing up my torso, she came hard a few more times. We were pillow talking to each other, and I told her how good her pussy felt. I’m telling you, we were like newlyweds. After a few more minutes or this, I pulled out and we got out of bed, where I turned her around. She slowly bent over, on her knees and elbows and put her face on the bed. I rubbed my long thick throbbing cock between her ass cheeks and gave her another little smack and asked if she was ready. She moaned yes, as I he entered her again. Just as she buried her face into the bed, Maria walked past the room. I didn’t know at the time, but Jessie had gone into town for more food and supplies, and left Maria sleeping. I think hearing her best friend’s parents fucking probably woke her up. So while I was pounding my wife, she tiptoed to the door and was looking in just as I looked up. Our eyes met, I smiled; she blushed, and nodded for her to come in.
I smiled at Maria, pointed over to the closet, and she quietly tiptoed in where she could watch. Amy was still blindfolded, so she couldn’t see a thing. I would slap her ass or pound her extra hard as Maria walked past so that all Amy could think about was the joyful pain I was inflicting. Once Maria sat and closed the door just enough to not be seen, I grabbed Amy’s perfectly curved hips and started fucking her hard and deep all over again. Being watched by a girl I actually wanted to fuck made me so hot I thought I was going to burst. And what made it even hotter was that Amy didn’t have a clue that I was fucking her while thinking about fucking her daughter’s best friend. I was going really deep, when Amy reached back between her legs and squeezed my balls. It didn’t take too much longer until I pulled out, and shot a huge load all over Amy’s back and ass. I was still hard, so I put my cock back inside her and pumped her a few more times before collapsing. I waved my hand for Maria to leave, and I watched her leave. She had cum several times, so her panties were soaked through. Before I took off Amy’s blindfold, I kissed her and decided to take a shower with her. Amy sneaked off quietly, and I heard water running. I knew she could not get back in the bed after cumming that much without a shower. I slipped away quietly and hustled back downstairs to sleeping Maria. I was so turned on thinking about her that I fucked Amy again in the shower, and later, I masturbated thinking about her. At one point, I remember dreaming, thinking about how hot it might be if my daughter was bi. I KNOW my wife is, but imagine my wife, my stepdaughter and her best friend – three hotties fucking each other and me in the middle. I know it’s naughty as fuck, but trust me, I have cum many days with that same dream!
The girls left the next morning. Amy and I were actually just about to fuck when they knocked on the door to say good-bye. We called them over and gave them hugs, I made a point of letting Maria see my hard cock up close before they ran out the room. I knew that Maria would never tell what she saw, and I hoped that one day, I would get the chance to give her what she seemed to want so badly from me…
But here comes the REAL secret… Fast forward 6 years!!!
I was in Chicago, at a medical convention and guess who walks into the hotel lobby??? Maria!!! I recognized her immediately and greeted her warmly. She recognized me and called me by my first name – no more Mr. or “Sir.” I told her why I was in Chicago, and would be staying for a few days. She told me she was travelling for another conference – in a hotel across the street and suggested that if our schedules synced up, that we should get together for dinner. We looked at our calendars, and decide on that night. As she walked away…I thought…”god damn, that woman is sexy!” Much hotter than she was that weekend she spent at our place. She turned back around, as if she could read my thoughts, winked, and that let me know that she remembered our unspoken promised. I was so turned on that I went back to my room and stroked out a nice midday load.
I found it almost impossible to concentrate for the rest of the day. I kept thinking about her. What would she wear? What will we talk about? I reminded myself that this was my stepdaughter’s best friend, but then I said, “she was almost grown then but she is surely grown now!”
After my last workshop, I went to the stylist to get a shave, and got myself in presentable shape to meet this hot young thing that if things would right would fuck my brains out. I went to the lobby, rang her room and told her I was there. I had on a nicely tailored black suit – trying to look as dashing as I could for my hot young companion. She had on a dress that made me hard just watching her walk from the elevator to the desk. I kept my composure long enough to say Maria, You look gorgeous” as I leaned in and kissed her on her cheek. I let the kiss linger as I wrapped my arm around her waist. She purred and began to melt into my arms, but I let her go just before we both forgot and said, “fuck dinner! Let’s go to the room!” I stuck out my arm, which she eagerly accepted, and we stepped into the limo I had waiting outside. We went to a very nice restaurant and had the best time. We talked about everything! It was fun catching up. She told me told him how much she enjoyed the time I spent at their house. We talked about that for a little while. Then she blushed and leaned in a bit and told me in a half-whisper how much she loved when he smacked Amy on the butt. She told me that she also had a little bit of a spanking fetish and found it to be a huge turn on watching me do that. I talked about Amy’s still tight and sexy ass, but then I confessed that Amy and I were going through a few problems and had separated. She could probably feel my sadness when I told her that I wasn’t totally sure if we would ever get back together. She touched my hand and said I’m so sorry Ron, which cheered me up enough to say “on a lighter note, tell me more about this spanking fetish” we laughed, and that and the second bottle of wine lightened the mood enough for Maria to tell me a little bit more. I was rock hard when I finally said…”well, maybe you’ll be naughty enough tonight that I will have to spank you”. She responded…”Ron, I sure hope so!” We had the best time at dinner; we really enjoyed each other’s company. It was very clear that we were both getting very turned on. It wasn’t just the wine – trust me. I would have been throbbing hard for her under any circumstance. I told her how great I thought she looked; she told me that she was glad we were able to connect again.
We left the restaurant and went for a ride in the limo. We enjoyed some of the sights of Chicago and sipped a little more wine. It was very romantic. We felt the connection so at one point, she scooted over next to me, she wrapped her arm around me, put her head on my shoulder. I pulled her a bit closer, and started to softly rub her leg. When I told her how much I enjoyed seeing her again, I leaned in for a polite kiss, she moaned softly, as our lips touched…
We got back to the hotel and I asked her …”well, is there anything else we can do tonight”? She looked up at me and said “Ron, would you like to come up to my room? We can continue our wonderful night”. I almost said, “Absolutely!”. A bit too fast. But I told her I wanted to change out of the suit and get into something more suitable for the next phase of the night. So I trotted across the street, and made a quick change. 10 minutes later, I was knocking on her door…
Maria invited me in, and before I was even fully in the room, I gently drew her to me, and we hugged and kissed. We sat and talked a little while about how much we enjoyed the evening, we sipped a little more wine, and when I told her how incredible she looked in the dress she wore, she surprised me by telling me that she actually wore it just for me – just so I would notice her. I smiled, and leaned back in the chair and said to her in a mocking voice “you are a bad girl Maria”. She looked at me with hungry eyes and said, “yes I am”. I got up and moved over to the bed and said…”you know what happens to bad girls, don’t you”? She smiled, enjoying the sexy banter and said…”What’s that”? “Come over here and I’ll show you”. She came over to the bed, and sat very close to me. In a stern voice, I told her to stand up. I took her hand and said, “now, lay across my lap”. As she did as she was told, I told her to put her my hands under my legs, she did it and looked back at me over her shoulder. I gently pulled her dress up, revealing her little sexy lace panties. I let out a moan when I saw them. Then I rubbed her mostly bare bottom and told her that unfortunately, those tiny panties won’t offer much coverage or protection for the spanking she was about to get. I rubbed her bottom, exploring and smoothing my hand over it thoroughly. I payed special attention to the underside and let my hands and fingers go deep between her legs. I could tell by the warmth, and the wetness, and her soft purrs and moans that she was getting aroused like never before. I told her in my authoritative voice that her perfect little ass needed to be spanked, and gave her a couple of light smacks. She looked back at me – I looked into her beautiful eyes, and said calmly, lift your bottom up. When I got her to do that, I reached between her legs and with my hand wrapped around my pussy, I pulled her up to where I wanted her. I told her, “Maria, spread your legs apart slightly; that’s it honey…now this ensures that you don’t tighten up and I will feel the spanking better. I was really getting hot. Then I said…”Maria, what happens to bad girls”? She said, “they get punished”? I said “be a little more specific.” She said, “they get spanked?” I said “yes, now let’s get going.” I rubbed her perfect ass cheeks until I could feel her total relaxation, then I drew my hand back and “WWWHHHAAACCCKK!” I smacked her ass as hard as I could. She screamed out loudly, a mix between pain and pleasure as she squirmed I rubbed her ass, telling her to hold still, and then…rubbed my ass and told me to hold still…..then……”WWWHHHAAACCCKKK” right across both cheeks! My ass was on fire. He was really spanking me hard. I yelled out…”OUCH”. I reached back to rub my bottom and he told me to put my hands back under his leg. He said “no rubbing”. “Bad girls need to feel the sting”. I told her to raise her bottom and part her legs. I did so… and… “WWWWHHHHAAAACCCKKKK!!!” This one covered the underneath side of my butt. I screamed out….”OUCH”. He then rubbed my little butt that was now on FIRE. He said…”Wow, you’re a tough bad girl aren’t you”? “I love disciplining tough bad girls”. Then, WWWWHHHHAAAACCCCKKKK!!!” She yelled out, “FUCK!!!!! My ass is on fire, Ron!!!” I was a little concerned that I might have hit her too hard, but she was breathing heavily, and moving her ass, making sure that my hand slipped between her cheeks. She said again in a soft, sexy, willowy voice, “My ass is on fire…daddy,” and when she said that, I felt a surge in my cock like never before. My hand went between her legs, and as soon as I sunk my fingers inside her, I could feel her warm wetness completely envelope my fingers. I moaned, “mmmm…what have we here? Feels like someone has a very wet pussy. I will deal with THAT in a minute…” I looked at her ass bright ass, but delicious looking as hell. I moaned as I knelt above her, one hand moving from her pussy to the crack of her as and back again. My other hand was on my cock, which had grown to throbbing. I looked down and said to her, Fuck! Maria, this is exactly how a bad girl’s ass should look! Glowing red and hot.” I let her rub her sore ass, which she did, almost masturbating as she explored the contours of her radiating bottom. I told her to take off the dress, she did so, revealing a gorgeous black see through bra and panties. For me, time for spanking was DONE, I wanted to get my throbbing dick in between those red cheeks, and between those tasty looking pink pussy lips!
I still had my hand on my cock when I turned her around and told her to take off her panties. I had been looking at her from the back most of this time, but seeing her face me, she looked like an absolute angel. She had on a front-snapping bra, so as she stepped closer to me, offering to let me unhook her, those perfectly hand sized natural tits bounced in my face. I put one in my mouth sucked until she moaned again. Then I took a step back. I stepped out of my jeans, and my cock sprung up like a toy. Her eyes widened, and she mouthed the word “wowwwwww,” and started to squirm. That told me that her juicy pussy was dripping and she needed something – like a hungry mouth or a hungry cock to help her out. She looked up at me, leaned in to kiss me, pressing her tits against my chest, then slowly kneeled. She looked up, and said, you are even bigger then I remember, as she began to slowly alternate between kisses and licks on my cock and balls. She gave me the cock sucking of my life! A few times, I reached down to feel her tits, but she pushed my hands away. “Now, it’s my time to take YOU over, sirrrrrrr…” She pushed me back on the bed, licked her way from my balls and cock, up my stomach chest and neck. Then she planted a full-mouthed tongue kiss on me that was better than anyone ever had. She lifted up and said, do you know how many nights I came myself to sleep dreaming about feeling you?” Then she reached back, felt for my rock hard cock and slowly put it in her. She whispered, “fuck, you are almost too big for me…ALMOST!” With that, she inched me inside her little by little, she even had a couple of small orgasms taking me inside. Finally, she sat up straight on my cock, and said, “you’re all in, honey. Now it’s my turn to put a whipping on you!” and she went to work on me…
Even though she was riding me slowly, softly deeply, I was determined to take back control. I said to her in a firm voice, “I’m going to make that pussy feel good Maria” She laughed, and said, “I got this baby. Take this pussy!” Watching her personality change from the demur hot young woman to this tiger in a see through push up bra was as hot as the fucking she was grinding out on top of me. She was grinding and bouncing, rocking her hips, taking my hands to give herself leverage. Her pussy was so wet that juices were flowing down my shaft onto my balls. She told me how big I was compared to her others, to my surprise, I managed to sneak in a couple of nice firm smacks on her ass. This time she didn’t yell; she just bounced higher and harder and said, “smack my ass good daddy!” I saw her facial expressions change, and then she started speeding up. She was moaning, “oh fuck, daddy, you got me good…fuck meeeeeeee!!!” and with that, she started to convulse, she gave a low groan, they she absolutely EXPLODED on my cock! She was bouncing uncontrollably; I felt her pussy tighten on me with each bounce. But by the third one, I felt my cock tighten and I said to her, “I’m right behind you honey…” My whole body started to jerk, and I could feel and hear the spurts of my thick, creamy cum shooting up inside her. But I was still hard so I flipped her over, spread those legs and rammed my cock in her so deep that my balls were making a loud slapping sound against her ass! She wrapped her legs around my ass and said, “I want you as deep in me as you were in Amy that night!” I literally felt my strength and my hard on come fully back. Her pussy was so good, I was fucking the way I was as a teenager.
Maria was taking my cock, looking down at me entering her, the sight of seeing my ramming my cock in and out of her made her cum again. She started kissing me deeply as we fucked. It was the best sex I ever had, and the fact that we had both been fantasizing about each other for the past six years made it even better! I couldn’t take any more. This time, to my complete amazement, I came again, even harder than I did the first time. Maria came again too, then wrapped her legs around me tightly and wouldn’t let me pull out. We laid there in a sexy, romantic sticky heap. It was beautiful, and totally intoxicating.
We showered together and when we did, I made a point of paying special attention to her red stinging bottom. We kissed and made out in the shower. After that, we got dressed and were going to go down to the hotel bar to get a drink. We walked out of her room and the older couple in the neighboring room was coming out of theirs. They had a look on their face…and expression that they knew something. The lady smiled and said…”Hmmm…sounds like someone might have a sore bottom, but it appears that it was quite enjoyable.” We looked at each other and laughed, we were so embarrassed. I looked the elderly woman in the face and winked, saying, “yep, sometimes a bad girl needs a spanking!” She looked at me as if she wanted a little of what I just gave Maria, as the husband continued walking down the hall. The lady said…”well, I used to be a bad girl myself” and she winked at Maria...
We decided to spend the rest of the weekend together. We ended up fucking several more times over the next two days. We spent it basically like a married couple – fucking, ordering room service, taking a swim in the hotel pool, coming back and fucking some more.
Since that amazing weekend, we have managed to keep in contact but that was the last time we ever made love. A year later, I let Maria know that Amy and I got back together. She told me she was happy for us. I said half-jokingly that maybe one day, she could come for a visit, and a threesome. She laughed, and said she might consider that.
By the way, for what it’s worth, Jessie never seemed to be aware that I fucked her best friend from college. She never knew that Maria and I spent a glorious weekend together, or that six years before, that she sat in a closet fingering her pussy watching me fuck her mom into oblivion. Who knows what might happen if she ever found out.
Here is the funny part of the story… Maria called me about a month ago asking me how things were with Jessi. She had been on her mind. Maria confessed that she has had a crush on Jessie since they met, but they never acted on it. I told her that she should tell Jess – it might do some good. She didn’t know that I overheard Jessie telling her mom how she felt. Amy told her to make it known, but not to expect much. Well, long story short, the two angels chatted, and Jessie and Maria confessed their years of unspoken desire. They planned to meet last month, but I have not heard the details. When I hear about that, I will be back with another story!
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