May I Mother,? SeXStoRY

This is based on a true story. All the names have been changed to protect their identities, It all started my sophomore year of college. I had been dating my high school sweetheart going on three years and things were going well for us. In high school, I had taken a lot of heat because Sheryl was younger than me. In those days, age mattered when dating someone. Now that I was in college, it really didn’t matter any more. The distance was tough at first, since Sheryl was still in our home town, but we managed to adjust and find a routine together. I’d make as many trips home as possible to see her, but it was definitely more fun when she came to visit. Debating between a college town and a trip back home wasn’t difficult with the usual weekend festivities in college towns. Since the drive from our home town to campus was about four hours, depending on who was driving, convincing Sheryl’s parents was often difficult. One occasion, however, went farther than my wildest dreams could ever imagine while asking Sheryl’s mother if she could come visit. Then, cell phones weren’t nearly as dependable and advanced as they are now, and with the expensive minutes, we spent most of our time communicating via MSN since it was free. It was a typical Thursday afternoon and I was done with classes for the day. My roommate played baseball for the university so his afternoons were spent at practice. It was pretty rare to get some “me” time in a dorm room that resembled a prison cell; it was so small. Sheryl’s mom, Cindy, was online so I decided to hit her up to give Sheryl permission to come visit this weekend. “Hey Cindy, I don’t mean to bother you at work, but I’ve got something to talk to you about if you’ve got a minute?” It took her a minute, but she responded as if she was honestly excited to hear from me. “Hey Scott…How are you?” We bullshitted awhile about school, grades, mid-terms coming, etc. but it was all just to warm up to her. My real intentions were to win her over so I could nail her daughter all weekend long. I’m just being honest. Finally, after thirty minutes of ass kissing I decided to finally just get right to the question. Cindy was a little hesitant, at first, but I could tell she was thinking about it. After all, the weather was going to be good so what was there to really worry about? “I don’t know Scott, it’s a long way for a young girl to be driving alone….I know you guys don’t see each other much so it’s really hard for me to say no” she says. “Cindy, I’ll do anything you want…anything…you name it…” I pleaded. Minutes, which seemed like hours, went by with no response. Did I push too hard? Is she pissed? These were questions racing through my head. I was trying really hard not to come off desperate, but in all honesty, I was. Cindy finally responded, which made me relax, but it was the response that I couldn’t believe. It was life changing, exciting, dangerous, and could she be fucking with me? There were thousands of emotions flying through my head, both heads. Let’s understand one thing first; I’m not the kind of smooth talking guy that’s good with words around the ladies. Moments like these typically made me choke on my own tongue. This time was different though. I didn’t have the confrontation of a face-to-face conversation. I was daring and brave behind a computer screen, though, and this was an opportunity to turn on my alter-ego. And, worst case scenario, I could deny, deny, deny. I could possibly get my roommate to cover my ass and say it was him on my computer fucking around in the chat rooms. That wasn’t uncommon, nonetheless, that was my story and I was sticking to it. “Hmm...I would do anything is a pretty bold statement to make to a lonely house wife, Scott...think you could handle it?” “You name it, and it’s done. No questions asked” I responded. Innocent reply, but yet, open ended enough that she could take it however she wanted to. Her requests were simple, yet dirty enough they could make me cum instantly. Cindy wasn’t the hottest MILF in town, but I certainly wouldn’t have kicked her out of bed unless she wanted to fuck on the floor. “Every time you cum for Sheryl, I want you to think about me…every time you masturbate…I want you to cum fantasizing about me” she said. That’s it? I thought. I could just tell her what she wants to hear. How in the world would she know if I actually did it? “You’re requesting something I’ve already been doing, Cindy. Are you sure this is what a lonely house wife needs?” I said optimistically. If she was as turned on as I was, she had to have been soaked. Just one touch to my cock and I would have blown my load right then. Cindy demanded confidently, “I want you to fantasize about me first…maybe one day if you’re lucky…I’ll make those dreams come true”. “Deal”… This was a double victory in my book. Not only does Sheryl get to visit this weekend, but, I could possibly get lucky with Cindy, too! My imagination went wild and the fantasies were never ending. The only problem was could I actually pull this off? The weekend with Sheryl went great. We had a great time partying and going around to the different bars. Since neither of us was twenty one yet, the selection of bars we could actually get into was slim pickings. Nonetheless, we made the best of it and enjoyed our time together as usual. Dorm room sex was always a little difficult, though. Having a roommate sl**ping eight feet from you tends to limit your options a bit. If it was up to me, I wouldn’t have any shame with him sitting there listening and watching. Sheryl, on the other hand, was a little bit more modest and lady like and would never go for such a thing. I wouldn’t be a guy if I didn’t try though, right? I can’t be called a pig and not try to live up to it! Even with Sheryl there keeping my attention all weekend, I couldn’t help but think about the deal I made with Cindy. It seemed awkward at first, but the more I thought about Cindy the more I yearned for her. Monday was here, Sheryl was gone, and back to the grinding wheel again. Typical Monday classes and then it was on to the lunch room for the weekend gossip fest with the usual suspects. Like usual, the afternoons meant no class and the dorm room to myself. After the busy weekend, a cat nap was in store for me as I made my way to the dorm. All alone and some wonderful imagery to reflect back on from the weekend made it a great time for some self satisfaction first, though. Although, there was one woman I couldn’t get out of my mind. Cindy. Was it the off limits status that she carried that made her so intriguing? Was it because she was my girlfriend’s mom? I couldn’t figure it out, but all I could think about was being on top of Cindy and giving her the submissive boy toy sex slave she wanted me to be. Thinking of a woman her age was a hot fucking turn on. She was experienced, sexy, demanding, and most of all, she couldn’t get pregnant. “No condom” to a college student has the same excitement level as a “fat k** in a candy store”. I laid down in my bed and closed my eyes, pulled out my cock and started stroking it while thinking of lying in between Cindy’s legs. She was a shorter woman, dark brown hair, green eyes, and maybe a little on the thick side. I wouldn’t call her fat by any means, though. Her breasts were large enough for a handful and her legs we sexy and fit. I may not be a typical guy, but long dark hair and some nice legs will snag my attention all day long. Mmmm…damn! It didn’t take me long to cum, but I sure did cum long and hard. One piece of the puzzle that never dawned on me was having the first opportunity to cum inside a woman. I had never had this opportunity before, or at least, not one without taking the risk of getting the chick prego. Just thinking about this made me excited! It was moments later, after I had finished cleaning myself up from the afternoon activities, that I heard my MSN “nudge” coming from my computer. It was Cindy. “Hey Scott…how was the weekend?” “You were amazing” I responded, with a smile on my face. A voice in the back of my head told me to be careful because you never know who is on the other side of a monitor, then again, that goes both ways. “I actually just got done fantasizing about you… the thought of having your sexy legs wrapped around me…unleashing my cum into your pussy… made my cock explode like a volcano.” I responded boldly. “…omg…Would you really consider doing that?” she asks. I eagerly responded, “Absolutely! You’re definitely MILF material…” “I had some alone time this weekend in the tub and couldn’t help but imagine your young hard cock pulsating in my pussy as you came in me….we need to set this up…Scott, if ANYONE ever found out about this our lives will be ruined” she said. “It would be worth it, Can you call me?” To Be Continued…

May I Mother,? (Part II) SeXStoRY

There wasn’t much hesitation in calling Cindy. Only in my wildest dreams did I ever think this would actually happen. Could she be serious? There was this big “what if” going on in my mind about this being a set-up. I mean, after all, I am dating her daughter and she could be setting this up to see where I morally stand with our relationship status. Even if she were to pull such a stunt, she would be just as guilty as I am, right? She could play it off as “playing along to see how far he’d go”. What I needed was black mail. I needed something along the lines of an insurance policy just in case this opportunity turned sideways. Cindy and I rarely spoke on the phone as it was far too dangerous. Not that chatting online was better, but at least we didn’t run the risk of someone listening in on our conversation. Besides, saved chat logs on a flash drive was the insurance policy I was looking for. Over the next few months, Cindy and I chatted on a daily basis and each day brought something new. It got to the point where she had to bring an extra pair of panties to work as she would soak right through the first ones before lunch. We discussed everything from oral sex to doing it in public, to swallow or not to swallow, if she would let me give her the shocker or not, and different positions. This woman was willing to do whatever the hell I wanted and I was getting tired of talking about it. Finally, I had decided to take a trip home to “visit Sheryl” even though my true intentions were much more disturbing. I made the drive to Sheryl’s and was excited to see her. As bad as it sounds, the odds of getting laid this weekend were heavily in my favor but it was a 50/50 chance of who it was going to be with – Cindy or Sheryl? In all honesty, it was a little unnerving to see Cindy for the first time since the hours and hours of chatting had began. Every conversation and fantasy raced to my head when I saw her – both heads. I couldn’t help but imagine her lying in the bathtub with her waterproof red vibrator named after me while sliding in and out of her warm pussy as she closed her eyes and begged for it to really be my cock that’s inside of her. “Hey baby,” Sheryl said as she ran up and hugged me. Oh. Shit. Reality just set in. I’m hugging Sheryl and looking at her mother that’s standing behind her as if it’s mating season and I’m just a buck on the prowl. “This is going to be an interesting weekend” I thought to myself. I got my bags unpacked and got settled in for a weekend of fun with old friends. There were plans made to go out on the town or just invite everyone over for a bonfire and some cold beers and I opted for the latter. Sooner than later, there was 15 or so of some old faces that I hadn’t seen in some time. It was good to catch up with old friends and tell funny old stories. I knew Cindy was inside and it only took about 6 beers to build the courage to go face her alone. She had been inside the entire night watching a movie as the rest of us “k**dos” were outside carrying away. I knew I’d be able to get a few minutes alone with her before someone came looking for me. I walked inside and sure enough, Cindy was curled up on the couch watching a movie on the Lifetime® channel. I sat down on the couch directly in front of her line of sight to the television and smiled. I ran my hand up her leg on the outside of the blanket and just paused – I waited for her to say something but there was just this moment of silence. It was if she knew exactly what I was looking for and she was more than willing to accept my silent proposal. She slid her warm hand up the inside of my leg and wrapped her fingers around my fully erected member. The Nike® shorts I was wearing gave her pretty simple access to such areas. She smiles at me and says, “it’s fatter than I expected and I’m going to enjoy wrapping my lips around it to milk your sack dry.” Never in my life has anyone ever talked so erotic to me. With a few pumps I came instantly in my shorts – loads after loads after loads. She smiled and withdrew her hand and licked it clean of all the warm stickiness. She leans up and bites my ear and says, “it’s not the right time, go get cleaned up before someone notices.”. My body was drained. I ran to the bedroom, dropped my shorts, and found some jeans to put on so I could use the “I got cold” excuse as my reason for changing. As I came walking back out, Cindy was gone, the TV was off, and I assumed she retired to bed for the evening. I went back out and sat by the fire and my mind kept racing back to five minutes ago. Right then and there is when I first realized that during an orgasm, absolutely nothing goes through your mind. It was so fucking erotic that I didn’t know what to do with myself. I was getting hard just thinking about it! It was the kind of orgasm that makes your body goes tense, your toes curl, and every thought flees your mind as your body and soul just explodes with an unexplainable feeling. I don’t think there is a verb in the English language that could accurately describe the sensation, but un-fucking-believable comes to mind. Sheryl and I later called it a night and retired to the bedroom. She was soaking wet and ready to jump my bones the instant we closed the door. This was out of character for her. Normally, she was kind of passive when it came to sex. It’s not that she didn’t want it, but she was more of a conservative girl. You would never find her riding my cock with the seat back while driving down the interstate with the truck on cruise control. That’s another story. Anyhow, the only thing I could chalk it up to was the scent I was giving off after just having the best orgasm known to mankind. I don’t think Sheryl had ever been fucked before, literally, and I was trying to think about Cindy but all I could focus on was Sheryl screaming “Ohhhhh myyyy fuckinnnng Goddddd” over and over. I was fucking her so hard that my sack was slapping against her clit and her tits were bouncing all over the place – (laughing in my head – good memories). It was always the slow, sexy, love making sessions that she enjoyed. I didn’t give her the option this time. It was face down, ass up, as I plowed in to Sheryl like a wild b**st on a****l Planet® with Mike Rowe as the commentator. The weekend came to an end and it was time to return back to campus on Sunday night. I said my goodbye’s to everyone before I headed out of town. Sheryl was sad to see me go but it was a feeling we were both used to after being in a distance relationship for quite some time. Oddly, though, Cindy was glad to see me go. I didn’t understand it until I got back to school and found an instant message waiting for me on my computer. The message was dated Sunday morning at 1:43am. She wrote me the message while listening to Sheryl and I fuck each other’s brains out. “Scott, I’m sitting here listening to you and Sheryl and all I can think about is how badly I want you inside me. It’s very dangerous for us to be around each other and I think it’s best if we try to avoid being alone – I hope you understand. I’m sorry.” I sat there in shock. “What. The. Fuck. Just. Happened.” I hadn’t even unpacked yet and shit already hit the fan. How could this be? What did I say or do? I was dying to talk to Cindy to try and save this. After all the chats, secret phone calls, fantasies, and minutes of ecstasy this past weekend, I wasn’t about to let this one just walk away. It wasn’t that I felt Cindy owed me anything, but I felt the need to conquer her. She was the forbidden fruit… I waited until Monday to instant message her so I could catch her at work and we could talk in private at length. Monday came and went and Cindy never signed on. Tuesday came, then Wednesday, and finally Friday and she finally signed on. It was late in the evening and everyone in her house had probably already gone to bed. In consideration of the time, I knew Cindy must have had a few drinks in her and that’s why she signed on. Being a college k** and its Friday night, she wasn’t expecting me to be home. She thought she was just going to sign and on and read all the messages I had left her – which was none. “Hey Cindy,” I said. “Scott, how are you?” she replied coldly. “Good…so, is everything okay? I haven’t heard from you all week! The last I heard from you is your message I had on my chat when I got home Sunday,” I replied. “I know. And I’ve been avoiding you because I don’t know how to act around you. I just think it’s best as I don’t want to get anyone hurt. Listen, I signed on because I wanted to invite you to the beach house this weekend and I know Sheryl would love it if you came. Maybe we can find some time to talk too so things don’t get awkward.” Cindy said. “I understand completely, Cindy. I know it’s a big risk and things could get really ugly if people were to find out. No hard feelings, okay? I would love to come to the beach house tomorrow. Count me in! I’ll call Sheryl and let her know I’m coming.” I pulled up to the beach house early the next morning as I was excited to see everyone again. Very rarely did Sheryl and I get two weekends in a row. Being there was a lot of fun. There were 4-wheelers, jet skis, great food, and relaxing on the beach drinking plenty of cold beer. As the day went on, things were fine and Cindy and I got along. I had kind of let everything go to help keep my mind of things to prevent any awkward moments. I guess in the grand scheme of things, it was a smart decision for either of us considering who my girlfriend is. That night we returned to the beach house and came up with this crazy idea of staying up all night, drinking beer, and smoking a brisket on the BBQ pit. I know it sounds like a good idea, but after being in the sun all day, swimming, and already having consumed double digit counts of beer, we were already in a losing battle. (For those of you that don’t know, smoking a brisket on the BBQ pit is a low heat and very slow method. Usually, smoking a brisket takes about an hour a pound so this could very well be a 12 hour cooking event.) Moving on. The idea was to start the brisket late at night and let it cook through until the next morning where it could be served for lunch. By 2am, the “cooking team” had all passed out except me. Looking around, it was pretty peaceful. The full moon, no noise except the tide rolling in, and myself was all that was around. I’ll admit, I was pretty trashed but I still had my wits about me. I sat in peace for a little while and pondered random thoughts in my head and…bingo. This was it. This was the moment of all moments. It’s quiet, it’s dark, and there isn’t a soul that’s coherent for miles. “Let’s go wake up Cindy.” When you walk in the master bedroom of the beach house, the bed is right next to the door. With the way her husband snored, I knew it would be pretty safe leaning in and subtly waking Cindy. I slowly walked through the house with all my focus on that bedroom door. I leaned in, tapped her on the shoulder a few times until she leaned up and looked at me. I waved for her in a follow me motion as my nerves starting going crazy. I didn’t wait for her, but instead I started walking back through the house and back outside to the deck below. If she shows up, then she knows exactly what my intentions are. A few minutes go by and I see her walk out in her mid-thigh spaghetti strap nightie. Her hair was a mess from sl**ping and she was half awake and I wasn’t sure if she had caught her snap yet. She walked up to me and kissed me and said “follow me”. Jackpot! This is it. I followed her down another flight of stairs to the ground level where all the jet skis where kept in the garage. She opened the door and pulled me in by my hand and told me not to turn on the lights. With the full moon out, no lights were needed. She walked around to the back of the Jet Ski trailer and climbed up while I quickly started removing every piece of clothing on my body. I walked around to the back of the trailer and found her lying face up on the Jet Ski with her white spaghetti strap nightie pulled over her breasts. I froze. “Wow” I said. All I could think about is this older woman lying in front of me with one little strip of hair coming from her clit and very perky nipples just begging to be sucked. She had her legs spread and hooked her legs around my ass and pulled me in close to her. She leaned up, grabbed my cock, and guided me towards her throbbing wet pussy as she leaned in and kissed me. Lube? No fucking way. She was so drenched that you could see her juices dripping down the side of the red Jet Ski seat. I can’t remember ever being that hard before. My cock was literally one solid piece of pipe that I was about to lay in her. The tip of my dick was pressed right against her lips and I could feel the heat radiating from her pussy. Her pussy was almost magnetic the way it drew my cock in towards her! Without any friction or hesitation, I slid all the way in to pure – 100 percent – ecstasy. It was hotter and moister than any woman I’ve ever experienced before. I could barely function. It was a natural reaction to start sliding in and out. I felt so primal – like a fucking cave man taking my woman and having my way with her. She also had something I had never experienced before – muscles. With each stroke as I slid out, she would squeeze her pussy and choke my cock. She could make her pussy so freaking tight it was incredible. We never said a word to each other. It was all body language and feeling. What seemed like days was probably only fifteen minutes. I fought urge after urge to pull out and cum all over her because I wanted it to last forever. Another new experience – her head jolts back, hands pulling the hair on the back of my head, and her legs tightened around my waist as her pussy soaked us with cum. I had heard about this before but never did I think I would experience it. She’s a squirter. It was everywhere and I fucking loved it. We were both drenched in her cum and it was erotically hot. I couldn’t help but taste it. I continued slowly sliding in and out and now that she came everywhere, it made the vinyl seat very slippery; thus allowing me to move easier. I reached down and rubbed her clit with my thumb and within minutes she came again. This time it wasn’t an explosion, but it was all over my hand. I licked her cum off my fingers one at a time just as she did to me after our experience on the couch the previous weekend. Her body was shaking, almost uncontrollably, and she leans up and demands me to fill her full of cum. I lunged forward trying to reach her deepest darkest spots of her womb as my legs straightened, toes curled, and head back – I unleashed every ounce of cum I had in my body into her. It was the first time I had ever came in a woman and it seemed to just go on and on. Finally, I collapsed on top of her as we both tried to balance on top of a cum soaked slippery Jet Ski seat. As soon as euphoria ended, we both jumped up and snuck to the ocean to rinse off. The both of us had to get in bed with our significant other and the last thing we should do was get in bed smelling like fresh cum and raunchy sex. We rinsed off in the ocean and dried off, returning to our original clothing. The smell of burning pecan wood filled my clothes from smoking the brisket which helped cover the smell of sex. Cindy and I sensually kissed before returning to the deck. She looked me deep in my eyes and said “you’re everything I could imagine and more – you’re the first person to ever make me do that…you know…cum everywhere thing.” I smiled, kissed her on her forehead, and told her “it was the hottest fucking sex I’ve ever had, or will have, and you’re un-fucking-believable”. Cindy returned to her snoring husband and I sat outside on the deck to finish the brisket to drink a celebration beer of my recent conquered conquest and to reflect on the most amazing experience I’ve ever had. I returned to school the following day and went on with life as if nothing had ever happened. Until this day, that night remains unknown to anyone else except Cindy and me. It’s our little moment on earth that will never be truly shared with anyone else. I don’t think it would be as erotic as the first time and therefore have moved on. To recreate that passion and excitement would be very difficult to do again successfully, and Cindy agrees. We both have moved on in to different times in our lives and do not remain in contact. As for Sheryl, that chapter, too, came to an end but not for quite some time after that special night. Looking back, it was very dangerous with the risk of damaging families and lives to the point of beyond repair, but if I had to do it all over again, I would. I believe an experience like that passes you only once in a lifetime and, in that quick window of opportunity, you must capture it. It’s not meant to be forever, it’s not meant to grow relationships with, but more so, it’s an experience that every person, man and woman, must experience in this life. Thank you all for taking the time to share this experience with me and I certainly wish each and every one of you the best.