3 comments/ 31407 views/ 21 favorites The Greatest Night By: available44xx A few weeks back I met a buddy at a local bar to watch a college football game. The place is a combination of a country bar with a dance floor and a sports bar off to the side with all of the televisions. The game was on the west coast so it had a late starting time and ended well after midnight. Being a Saturday, the bar had a big crowd with a lot of people getting quite drunk. I had four or five beers and was feeling good but I was nowhere near shit-faced drunk. My buddy took off when the game was over and I headed to the restroom before heading home. The bar was pretty good sized and had bathrooms in a couple of different places. I headed to the one in the back corner because it usually didn't have much business. When I got there, there was only this fat dude taking a piss. We exchanged nods and I finished my business just as he did. I was about to walk out the door when this tall guy walked in with a blonde women. He locked the latch on the door and then just gave us a big grin and a wink. He started making out with the blonde who was obviously drunk off of her ass. When they came up for air, I recognized her as a woman I work with. I am the assistant principal at a local elementary school and she is one of the teachers. Her name is Debbie Shearer, and technically, I am her boss. Debbie is one of the most beautiful women I have ever seen. She is blonde and blue-eyed with a perfect body. She is around 35 and has been divorced for several years. She is very professional but has a bit of a reputation for being a partier. I really like her and have had a secret thing for her ever since I started working at that school. She doesn't dress or act seductively at work, but you just can't hide something like that. She has it, she knows she has it, and she knows you know she has it. Debbie has held center position in my sexual fantasies for a couple of years now. I didn't know what to do next. I was pretty sure they were going to do it right there, but I know her and am her boss. Should I intervene? Should I leave? Should I watch? As I was going through my moral dilemmas when she looked up at me and Fat Guy and kind of smiled. She then turned her attention back to the other guy. She was so drunk that she kind of realized we were there, but not really. I was pretty sure she didn't recognize me. I just kind of stood there with Fat Guy while they started making out again. Debbie looked so hot. She was wearing a western shirt, the ones with the snaps for buttons, a short denim skirt and cowboy boots. She then told the guy she came in with, "I want you." He responded by ripping open the snaps on her shirt. The most perfect set of titties in the world rolled out. Round and firm with beautiful nipples. I almost fainted when he did that. She giggled when he exposed her and then he started pawing at her boobs. I cannot adequately describe how it felt to have the girl of your dreams suddenly dropped in front of you like this. I was looking at Debbie Shearer's titties! The ones I wanted to see more than any others in the world. I was watching her get turned on as the other guy played with them. I was in heaven other than wanting to be that guy. She turned to him and got down on her knees and undid his jeans. She pulled down his pants and then his underwear and his cock popped up into her face. It was huge. Long and fat with heavy balls. It was the type of cock a woman like her fucks. She kind of gasped when she saw it and I realized that he had picked her up at the bar and this was her first look at it. She grabbed ahold of it and started slowly stroking it. I thought I would cum in my pants. She put it in her mouth and started sucking on it. Slow and long drafts on his big cock. She took him in deep into her mouth and throat. She knew how to suck cock. At that point, I noticed Fat Guy had pulled out his own cock and was jacking off watching them. What a great idea! I took out my own and started enjoying the show even more. I was jacking off in front of the most beautiful girl in the world! Then Fat Guy got out his cell phone camera and started videotaping the show. The guy is a genius. I did the same thing. The other guy then took off her shirt. God, it was the hottest thing I had ever seen. He then turned her around and leaned her against the long sink/counter in the restroom. He unzipped and pulled down her skirt and she was naked other than her sexy panties and boots. Then he pulled down her panties and threw them to me. Debbie was completely naked right in front of me. I was afraid I would cum right then and there. I wanted to hold out and enjoy this more. Then I watched him stick his cock into my fantasy girl. I watched her grimace and then almost smile. He started pumping her good as I watched hypnotized. Those beautiful boobs bouncing to the pounding. That perfect ass pushing back at his cock. I would have paid any amount of money to see this. No porno was ever this good. No sex that I had ever had turned me on this much. I was getting pretty close to cumming when she looked up at me and smiled. She pointed her finger at me and motioned for me to come closer to her. Then Debbie Shearer grabbed ahold of my cock and started stroking it. This was the greatest moment of my life and my life has been a good one. She played with it while the other guy fucked away at her. Then she pulled it closer and put it to her lips. She kissed my dick and put it in her mouth. She started sucking my cock. She sucked it hard and deep and I had never gotten a blowjob like this. At this point, Fat Guy did the greatest favor any guy could do for another. He took my cell phone from me and started filming the action. She was sucking my dick and I started playing with her titties. I could have played with them forever but I started to cum. I came in Debbie's mouth and she swallowed. I think she liked it and tried to suck me dry. Then I felt her shudder as she started to cum on her own. The other guy had hit the mark. She eventually turned around and went down on him again to finish him off. He was half hard and Debbie was still wanting cock. Instead of going down on her knees to suck him, she bent down and kind of stuck her ass at me. My cock was starting get hard again and I couldn't resist. I put it in her pussy and went to it. My God, I was now fucking Debbie Shearer. I know the other guy's cum was in her with my dick but I didn't care. This was the most beautiful piece of ass I had ever seen and I couldn't stop. I fucked her hard and fast while she sucked his cock. Then I came a second time as hard as I ever have. Then she did too. I made Debbie cum! I was a god. Things wound down quickly and they quietly put on their clothes. She didn't look back in my direction as she wobbled out the door. Fat Guy grinned and gave me a high five. He handed me her panties and said, "I think she left these for you." What a souvenir? He also gave me back my cell phone with the priceless video. I went home and quickly uploaded the video to my computer. It was better than I could have hoped. I had video of Debbie Shearer naked and having sex with me. This was the greatest night of my life and I got to relive it. I jacked off three more times that night. I was concerned about the following Monday at work. Would she remember what happened when she sobered up? Would it be tense? Would she press charges? I was really nervous when I drove to work that day. A couple of hours into the school day, she came by my office and asked about a student. It was all business as usual which relieved me greatly. I don't think she remembered a thing. I also wonder if she remembers the bathroom at all. She was three sheets into the wind. It is almost the end of the year. My plan is to ask for a transfer to another school. If that happens, I am going to ask Debbie Shearer out. I would have lost my job if I did that while she worked for me. Once I am at a different location, it is not an issue. I don't know if she will go out with me. I just have a bit more confidence now. I really shouldn't, but because of that one night in the restroom, who knows. The Greatest Night (We Never Had) I remember it like it was yesterday. You had just been promoted to Sergeant. I was so proud of you. You were so proud of yourself. It was a long time coming and we were both happy that it did. We went out to dinner with our friends to celebrate. Everything was perfect, but I wanted to do something extra special for you as a gift. I was not sure what it would be, but it would turn out better than either of us ever imagined. Cynthia showed up about 20 minutes earlier than we asked but said she felt you deserved it. She had a congratulations card for you. She had been a friend of the family for a couple years and a great baby sitter. She was young, cute, enthusiastic and had the kind of body I can only imagine I will ever have again. She handed you the card and stretched up on her toes to kiss you on the cheek. I watched and pretended not to notice, but something about it got my brain ticking. At first I was thinking it was silly jealousy but later realized it was something different. Dinner was great. Everyone laughed and had a good time. It was just the sort of evening that never seems to come. It seems like we try so hard to have those special nights out but something always seems to happen. But that night was different. It was special and I will remember it for the rest of my life, and I imagine you will too. We were having a great time but needed to be home. Cynthia had an appointment the next morning to register for a second semester at the community college. She was so excited, just turned 19 and was looking forward to starting her Nursing Certification Program. We got to the house and you walked me inside. I went into the living room and Cindi was sleeping on the couch. I could not get over how much I was noticing her body and the feelings it was causing. I suspected they were related to the kiss she had given you earlier, and convinced myself I was being silly. I woke her up and helped her find her shoes. She told me the boys had pestered her and she let them stay up an extra hour and hoped we would not be mad. I giggled as I handed her the money and said 1 hour was actually an improvement. I told her you were in the kitchen waiting to drive her home like usual and she smiled and hugged me like normal but before she let go, she said she wanted to ask me something very personal if I would not mind. Of course I agreed and walked her down the hallway and told you we would be out in a few minutes. We had some "Girl Talk" to attend to. I had no idea how right I was. You opened a beer and sat down to see what was on TV. We went to our bedroom and sat down on our bed. She was quiet for a second, but then asked me a question I never expected to hear from anyone. I told her I would help her if I could and we began to talk. You were waiting patiently in the living room, but when you realized you had finished the beer you were sipping on, you decided to walk down the hall to see what was going on. When you got to our room, the door was still open. Cindi was sitting on the bed with her back to you. I was kneeling in front of her on the floor. She was watching intently and did not notice you walk in, but I did and a rush of excitement flowed over me when I saw your reaction to what I was doing. I was holding my dildo in my hands, cupping it gently, caressing in, kissing it and sucking it while Cindi watched. She had told me her boyfriend had asked her for a blowjob but she did not know how so she asked me to teach her. She watched as I kissed it, gliding my tongue over the head. I peek up and see your eyes stretched wide as you try and take in the scene. I smile to myself as it occurs to me what your special present will be. After I finish my demonstration I look up at Cindi and ask her if she is willing to try. She is silent for several moments and you turn for the door but I catch your glance before you go and silently shake my head, signaling I did not want you to go. I remind Cindi that we were there because she asked and assured her that if she wanted to think about it and consider lessons later, I would understand. She finally looks up from her hands and whispers to me she wants to try. She reaches to me for the dildo, but what I did surprised us all. I placed the dildo on the floor behind me and take her hand in mine. I tell her to kneel on the floor next to me and with my other hand I call you forward. I sit you down in front of us on the bed as Cindi kneels next to me. She asks if I want her to suck on the dildo while you watch and I say no. I want her to practice on you. She catches her breath and your eyes stretch even wider. She tells me she does not think she can do it and so I begin to whisper in her ear. "You will do fine." "Go ahead, he will never complain." "This is your chance to learn first hand." She stares at the floor for several minutes and finally looks up into your eyes. You are watching her intently and I can see the excitement has already begun to manifest itself as your jeans become tighter. She looks back at me and I take her hand in mine, kiss it and then place her hand on the thigh of your jeans, just inches from the bulge that has developed. I brush a lock of hair from her cheek and suggest she feel it thru your pants. As she does, you begin to squirm on the bed. I look up at you and smile. I have found the perfect gift and am so excited to be here to share it with you. I urge her to reach for your belt and eventually she does. She unbuckles your belt, and begins to open your fly. She looks over at me and I smile and tell her to do what I showed her. I pick up the dildo again and begin to kiss the head. She finally pulls your cock out of your boxers and holds it, staring. I get right up next to your leg, put the dildo out in front of me and lean forward to kiss it. She mimics me and the sight of her kissing your cock sends a flash of excitement thru me. I stick out my tongue and glide it along the shaft and head of the dildo and she continues to copy my actions. She is nervous, but we all are. She is clumsy but from the look on your face, I know there is no chance of you complaining. She finally opens wide and guides your throbbing cock into her mouth. She is shaking but getting smoother with every action, every stroke. You reach down and cup her head in your hands. I love when you hold my head like that massaging my scalp and I feel the lips of my pussy twitching with excitement to see you doing it to someone new. She is becoming better. She stops on occasion when the excitement gets the better of her and she goes farther than her throat is ready. She gags and coughs several times. On one incident, I am convinced she is going to throw up but she recovers and goes right back to work. The next thing that happens was something I never considered, but watch her sucking your dick like that, it seemed like the most natural thing in the world. I move from beside her on the floor to behind her. I lift the back of her skirt and see her sexy ass, firm little cheeks in a glittery thong. I had never looked at another woman with as much passion and excitement and interest as I was looking at her now. I lean forward and gently kiss her ass cheek and her body twitches. In her excitement, she bites you and you moan with pain and passion. I glide a finger under her thong along the lips of her pussy. They are firm, tight, and not a single strand of hair. I slip a finger inside and for a brief moment, I pause to think. We have never done anything like this. I have never once considered any sexual activity with another woman, but the need to taste her sweet pussy overwhelms me so I slide my finger out and immediately put it in my mouth. I had tasted my own pussy before, on your fingers and my own, or on your cock, but was not prepared for how strangely similar, and yet different her pussy tasted on my hands. I lean forward and begin to blow on her pussy lips as they hug her thong. I slide the thong to the side and begin to lick her pussy. The excitement takes control of my mind as I grab her in both hands, spread her lips open and stick my tongue inside her. I kiss her pussy again, then get up on my knees and kiss your lips, making sure you taste her nectar on my lips. As I back away, you tell me you are getting close to finishing, I reach for Cindi and back her away from your cock and you lean down and kiss her mouth. I explain to her that swallowing cum is something that many girls do not like for whatever reason but tell her I was going to show her something no guy will ever complain about instead. When she agreed, I grab her shirt and lift it up over her head and throw it behind me. I reach over and cup her gorgeous C Cups in my hand and pull them out of her bra. I toss the bra behind me also and her perfect tits are hanging there, barely lower than they were in her bra. I kiss her nipple as I wrap my hand around your cock and begin to stroke. I tell her to stand up and let you suck on her tits. You take her nipple in your mouth and begin to massage her ass. I am stroking your cock and take it deep in my throat. I tickle your balls and suck you deep until I taste the first drops of your precum. I tell her to kneel down with me again as I continue to stroke you. Your cock pulsates and throbs in my hand as the cum explodes from you, splashing on her tits, her neck, the smell of sweat and passion filling the room. Your cum glistens on her skin as I lick the head if your cock to get the last dribbling bits and then I rub my hands on her chest, spreading the cum evenly across her tits, nipples, neck and shoulders. She is there beside me, chest covered in your cum. A huge grin of pleasure and satisfaction was on your face. You take her hands and help her up to her feet. I hand her the blouse that was thrown away, but as she starts to put in on, you did something that excited me in a way I never imagined. You stop her and pull her hands down and take her nipple in your mouth again, licking, sucking, scrubbing the cum off then you kissed me on the lips, sharing your cum with me. A wave of passion washes over me again and I can feel my own pussy beginning to pulsate and drip. The three of us kiss and discuss the possibility of a future lesson, and you take her home, leaving me to finger myself and use my toy and anticipate what will happen when you get home as another wave of excitements shudders thru my pussy.