The Woman from My Past Who Took My Virginity

Discussion in 'Erotic Literature' started by realwrl, Apr 7, 2014.

  1. realwrl

    realwrl Member

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    So I brought lunch back to the office the other day and was just surfing the net while eating a burrito when a message popped up in my email... "Remember me...???" Normally, I'd just delete something like this and write it off as spam, but since I was eating lunch, I opened it. It actually was from someone I knew. If you've got a little time, check this out and let me know what you think.


    To give you a little back story... this was back in high school. Summer after junior or senior year, I really can't remember. Anyways, I was looking for a job of some sort, nothing serious, just something to make a little money. So I'm going through the paper one day and there is a short ad looking for someone to learn website design, entry level position.

    I had always been interested in design, so I called them. Spoke with a lady who explained she had a small company that was helping local businesses with their websites. She worked from home, but was looking to expand into a small office that could fit 2-4 people. She asked me in for an interview, so we setup a meeting at her house.

    So a day or two later, I drive up to her house (it was in the hills, but I had a friend who lived nearby so I knew the way). I had never had a job, let alone an interview, so I was extremely nervous. When I got to the house, her husband (I think it was her husband) answered the door, and invited me in. He directed me to her office where she was sitting at her desk. Her office was huge! This house was huge. Upon entering the office, I immediately noticed how put together this lady was (if I worked from home, I'd be in my PJs or underwear all day).

    She invited me in and asked me to shut the door behind me which I did. She asked me to come sit down at the desk where she walked me through some of the projects that she had worked on and what she'd be looking for me to do. After explaining everything, she asked if I'd be interested, and I said YES, DEFINITELY!

    At that point, her husband walked in and asked if we'd like lunch and she said we'd be quite a bit longer because I was interested in the job and she had more to show me, to which he said OK and closed the door.

    What happened next I could have never imagined or expected. I was sitting next to her while we had been looking at her computer, and she turned to me, putting her hand on the inside of my leg while sliding it up to my cock while saying, "I'm interested too".

    I'm 17, I'm a virgin and I have a VERY good looking woman touching my cock telling me she's interested. All I could say was, "OK".

    At this point, I was rock hard. My teenage hormones were going crazy. She turned my chair and positioned hers in front of mine and began undoing my belt. She asked, "Is this OK?".

    I nodded. She unzipped my pants, "Is this OK?".

    "Yes".

    She asked me to stand up and take my shirt off, so I did. She slowly pulled my pants down until they were on the floor around my ankles and commented on my erection. I always wore tighties in high school, never boxers, had to have some way to partially hide my boner when I was in class. "I think it wants out", she said to me.

    I had to tell her that this was my first time, "OK, but I've never done this before", I said. "I know", she replied, "All you have to do is keep your dick hard for me. Can you do that?"

    My heart was racing and it felt like it was pumping all the blood directly into my dick. My cock was throbbing and she could tell. "Yes, I think so", I said. Still unable to believe that this was happening.

    "Good", she said. "And after I make you cum for me, I am going to need you to get hard again. Okay?"

    I looked down and she was still gently stroking my cock through my underwear and my precum was already soaking through. "I will try. I usually only jack off once."

    I couldn't believe I said that, when she followed up with, "You WILL get hard. I will be the one trying. I will try to keep your cock as hard as it is right now after each orgasm I give you. Is that OK?".

    I didn't know what to do, or what to say. I had never had sex, not even a hand job and this hot woman with amazing tits and a beautiful smile was telling me not only that she was going to get me off, but she was going to do it multiple times. The only thing I could say was, which came out as a mutter, "Yes ma'am".

    She squeezed my cock through my underwear hard and tight and said, "That's what I like to hear".

    I was so horny, so hard, and so ready for her to take my cock out of my underwear, but at the same time had that nervous thought in the back of my mind... that feeling that I was going to cum as soon as she did. I can't explain the anticipation, this was like something that you'd see in the movies and it was happening to me. She then said, "I'm going to let your cock out now. I need you to tell me when you are going to cum, okay?".

    "Okay", I said.

    She slowly pulled my underwear down with her fingers, keeping both thumbs on the under side of my cock. My cock had been push to the right in my underwear and she used her thumbs to guide the tip out and let it stand. I could feel it throbbing. With each throb, a little stream of precum dripped to the floor. She left it there and watched it for a little and asked me, "Do you know what that is dripping from your cock?"

    "No", I said (because I really didn't know at the time).

    "That's called precum. The fact that you make a lot of it is a very good thing. I like precum. Its a natural lubricant and I'm going to use it to stroke you, suck you, rub on my tits and eventually... fuck you."

    I was so close to cumming and this woman hadn't even really touched me yet. I remember clenching my butt cheeks so hard trying to keep from orgasming... I wanted this to last longer. "Yes ma'am", I said.

    "Good", she said as she guided my underwear to the floor. Running her hands back up my legs and over my balls to the tip of my cock. She was touching me so softly, not trying to make me cum (or so I thought), but her teasing me was driving me crazy, and looking back now, I think she new it. Then she went down to her knees and looking up at me, opened her mouth at the tip of my cock. She rubbed her index finger over the hole of my dick then spread it with two fingers. This opened the way for a large drop of precum, to which she didn't flinch, she just opened up and stuck her tongue out. It dripped directly into her mouth and as the drop finished, she licked the tip of my cock and this sent me over the edge.

    "I'M GOING TO CUM MA'AM!"

    To which she immediately took the entire length of my cock into her hot wet mouth. I could feel my tension releasing. I could feel the semen pumping out of my dick. Spurt after spurt. She didn't come up for air. She kept her nose buried in my pubic hair and fondled my balls with one hand while she pulled me deeper into her throat with her other hand. As the last of my load made its way down her throat, she slowly pulled away from my dick, sucking me every inch of the way, paying extra attention to the tip when she got there. Once my cock was out of her mouth, she said, "Good boy. Now remember what I told you. You need to stay hard for me."

    Hearing that sent a rush of blood to my cock and I was immediately ready to go again. Being 17 was one thing, but hearing a grown woman talk sexually to me was such a turn on. She stood up, keeping one hand around my cock and led me across the room to a door (not the one I came in). "Did you like that?", she asked as she opened the door.

    "Yes ma'am, very much".

    "Have you ever had a blow job?", she asked me.

    "No. Not even a hand job".

    "Poor boy. I should have asked you what you wanted.

    "That was fine, ma'am. It felt REALLY good".

    "Well I'm glad", she said as she led me into the new room by my cock, "I've noticed that you have been looking at my tits since you got here, do you like them?"

    This caught me off guard. I mean, I was looking at her tits, but I had never had a woman be so direct with me, so I answered the only way I could... honestly. "Yes ma'am. I think your tits are amazing", I said.

    "Do you think you can undress me while I hold your cock?"

    "Yes ma'am, I will try". She was still leading me across the room to a bed. It was a large room, but no pictures or anything. Looked like a guest room or something. She stood at the foot of the bed and slowly stroked my cock, more or less waiting on me. I slowly unbuttoned her white blouse (which she had left a few too many buttons undone) which covered her massive tits. She had a black bra on that pushed her tits up and together so nicely. Again, another first for me that made my cock pulsate. I could feel her rubbing the tip and spreading precum all over my cock. As I took her blouse off, she switch hands on my cock then told me to take her skirt off. It unzipped from the back and just fell to the floor. She had no panties on and her pussy was shaved clean with the exception of a tiny little strip of hair no more than an inch long, right above her slit. She took a half step back, while keeping my cock in her hands (both hands now), and asked me, "Do you like?"

    I was speechless. Here I was, with a woman who was probably nearly twice my age (could have been 30-35... I'm so bad with age... especially back then). She had the type of body that I would have masturbated to had I been alone at home and flipping through a magazine. My cock was going crazy in her hands and she was doing a great job working all of my precum onto my tip and shaft. "Yes, you have an amazing body."
     
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  2. realwrl

    realwrl Member

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    "Good. I'm glad you think so. Before I let you satisfy it, I'd like you to get something that you want. Since you like my tits, would you like to titty fuck me?"

    Again, I could feel my cock throbbing and pulsing... I was so anxious I could tell I would be quick to cum. This woman was so sexually open and free (or it seemed that way to me since I had never had sex).

    "I would love that", I said... and I meant it. This was a fetish of mine at the time. I had masturbated to the thought of titty fucking so many different girls that I went to high school with, and in the one magazine I had hidden under my bed, I'd always turn to a page of a cock between a nice pair of tits when I was about to finish. It was almost like this woman knew that.

    "I thought you would", she said as she sat down onto the bed and pulled herself back to the middle of it, "We're going to need to put some of your precum to use now. I don't like using oil... I like natural lubricant. Do you think you can make enough to lube up my tits?"

    I was in shock, standing at the foot of the bed, looking at this woman laying in front of me rubbing her tits with the precum that she had on her hands from stroking me. "Yes ma'am, I can do that", I said.

    "Good, get up here and straddle me." So I did. I knelt over her with my erection shooting straight out, and immediately a big drip of precum streamed down and landed between her tits.

    "Good boy. Keep that up and you'll be titty fucking me in no time", she said as she reached up with both hands and more or less started milking my cock for precum. With one hand, she rubbed my balls and massaged my taint and with the other, she stroked the length of my cock, starting at the base and squeezing tighter and tighter as she got toward the tip, paying close attention not to touch the tip of my cock (she probably knew I'd cum). With each slow, squeezing tug, she would get a long stringy drip of precum. I was so fucking horny, and was in absolute heaven watching my own cock being slowly stroked, dripping precum on the nicest set of tits that I had ever seen in person. As her cleavage became more and more wet, she began alternating tits to drip the precum on. Once she had some on each, she took her eyes off my cock and looked directly at me, "Are you ready to titty fuck me now?"

    I was so ready, and didn't know how long I could last. "Yes", I said, "I can't wait."

    "I can't either. You have such a nice cock for a teenager. Grab my tits and slide it in between them... and remember what I told you earlier", she said.

    "That I need to keep my dick hard for you?", I asked.

    "Yes", she said, "That and you need to tell me when you are going to cum, okay?"

    "I'll do that ma'am", I said. "Good, because I want to taste your cum again. And we're in bed now. Call me mistress.", she directed me.

    This woman seemed to know everything to say to me to make me HOT. My undersexed teenage cock was throbbing again, "Yes mistress", I said back to her.

    As I reached down and grabbed her breasts and lowered my cock between them, I quickly learned how difficult it was to control big, natural tits that were covered in slippery precum.

    She giggled a little as I fumbled, and said, "You have big hands. Grab them and squeeze them around that beautiful cock of yours."

    So I did, I reached down around her sides and wrapped her tits around my long hard shaft and squeezed.

    "Yes, Mistress", I said as I began to thrust. This was a dream come true. I had my dick buried deep between a wonderful pair of tits, and the lube was my own precum that had been slowly stroked out of my willing cock. I finally found a rhythm and gradually began to increase the pace.

    She began moaning and talking to me, "MMMMMMMMM.... YES! Fuck those titties!"

    This sent me over the edge. Like before, just not used to hearing a woman talk dirty... I had seen porn, but in person was a totally different experience. She probably could have made me cum without even touching me. I tried to fight my oncoming orgasm, I felt my legs and ass tighten up again as I tried to squeeze to hold it, "Mistress...", I exhaled.

    "Are you ready to cum for me?", she asked.

    "Yes. Yes, Mistress. I'm going to...", before I could finish, she lifted her head of the bed and swallowed my dick. This time, she bobbed her head on it as I came. With each stroke of her mouth, I could feel her "pulling" more and more cum out of me as she massaged my balls and sucked my cock. As I finished, for the second time, she continued to play with my balls. She made a ring with her fingers around the base my scrotum and began to pull my balls down as she slowly pulled her mouth off of my cock.

    Looking up at me, she pulled harder and harder, and said, "You're going to be a good boy and keep your cock hard for me, right?"

    Looking down at her, I don't know whether she knew it or not, but my cock would have stayed hard for her all day and all night. I was a teenager who was shocked to be having sex and I was growing more and more horny and ambitious by the minute. "Yes Mistress", I said to her.

    "That's a good boy. Now it's my turn to enjoy this beautiful cock that you have. Lay down on your back", she said as she released her grasp of my balls.

    I did as she said and she pulled some ropes out of the dresser drawer. She tied one on each of my arms and looped each over the bed post at the head of the bed.

    "This time, your legs will be untied. Next time will be different." After securing my arms, she crawled back onto the bed and straddled me, above my chest. She reached behind her and stroked my throbbing cock a few times, before saying, "You're ready". At which point she slowly inched her way up and rubbed her pussy on my face. Not know what i was doing, I tried to stick my tongue as deep as I could. She was very moist herself and had a salty taste.

    "That's good", she told me.

    Then she got off and reached into the dresser drawer. She pulled out a condom and opened it. She took the condom in her mouth, lightly holding it between her lips and proceeded to crawl between my legs and without using her hands, she slow rolled the condom onto my hard cock using only her mouth (and maybe a little bit of teeth). I was going to have to tell my friends about this. I had put a condom on myself before (and jacked off into it), but I struggled so much just to get it on. She put this thing all the way on me... with her mouth.

    "That should do”, she said, “Are you ready to fuck me? I want to feel your big dick stretch me", she said while crawling back up and straddling me.

    "Yes, Mistress. I want you. I'm so ready." I was ready. I was so horny. I never wanted it to end, but I was so ready to dive in and get more. Everything she did to me felt so good.

    "Good boy", she said as she lowered herself onto me. She was so seductive. She moved up and down on me slowly a few times, then sat all the way down and grinded on me for a little bit, then she asked, "Do you know why I left your legs untied?"

    I had no idea why, so I kept with the honesty policy, "No, Mistress. I don't know why."

    She began to move from her knees to her feet while saying, "I'll show you why", she continued until she was on both feet in a squat position, the tip of my cock still inside of her, "So you can fuck me. I want to feel you thrusting up into me. And this time, when you tell me that you're about to cum, I want you to keep fucking me. Okay?"

    This was unexpected... I thought she was tying me up to take advantage of me, but I was so horny that I didn't care. I wanted to feel my cock in deep inside her more, so I said, "Yes, Mistress. I'll keep fucking you until you tell me to stop."

    "Good boy", she said, "You can start now. Fuck me like you want to fuck me... slow and steady or hard and fast. It's up to you, but DO NOT stop fucking me when you cum. I want you to fuck right through your orgasm."

    With that, I pulled my feet back and slowly began to lift myself into her, deeper and deeper.

    "Good boy", told me, "That's it".

    I pulled against the ropes that were around my arms for some extra leverage and braced myself against my elbows and heels and found a position that gave me the ability to make nice long thrusts. I continued at a slow-medium pace as we both moaned. Hearing her moan and see her enjoy my dick got me going and it made me increase the speed and intensity of my thrusting. That's when she screamed out, "Oh yes! FUCK ME! FUCK ME!"

    I felt like I was in a porno... was this really happening? I did as she asked and I fucked her as hard and as fast as I could, until it came.

    "Mistress, I'm cumming!"
     
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  3. realwrl

    realwrl Member

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    Like she asked, I kept fucking. It was hard to continue fucking her as my body convulsed with pleasure. Each thrust was harder and yet more pleasurable.

    "Don't you dare stop!", she said, "You keep fucking me like that. You keep going".

    So I did, as my body quivered with pleasure, I tried to keep thrusting into her with some rhythm. My thrusting slowed down, but it didn't stop. I kept going for her. I was afraid she'd kick me out and say we were done if I didn't do as she asked. My cock was so hard and I could feel her pussy getting more and more wet. It seemed as if it was opening up for me to go deeper and deeper into her, so I kept going. I was in ecstasy. I felt like I was going to pass out from pleasure. I had tried to jack off for past my orgasm before, but I always got to a "stopping point", but with her, I wanted to keep her happy. I wanted more. I wanted to be invited back. My body was convulsing so rapidly and violently, my dick was as hard as it had ever been, I literally thought I was going to pass out, when all of the sudden... BAM! She slammed herself down onto me and started fucking me. I just laid there and she grinded me so hard and fast. She started to moan and scream and then it happened. Her pussy exploded. She started squirting juices all over me. I felt it running down my shaft, down my balls, across my stomach and down my sides. The heat and warmth excited me and I started to cum again. Another orgasm in the same condom. I had originally thought she was pissing on me. At 17, I had never seen that in my porno adventures. She lifted herself off of my cock and while rubbing her clit, she continued to squirt. As she collapsed onto the bed next to me.

    "Wow", she said, "No one has ever made me squirt."

    "Squirt?", I asked.

    "Yeah, that was amazing! Your cock is amazing!", she told me.

    "So that wasn't pee?", I asked (innocently).

    She laughed at me and explained that it was it was more or less the equivalent of a male ejaculating.... except in her case, a lot more! As we laid there, she winked at me and asked, "You're still hard, right?"

    I looked down at my cock, and it wasn't the long hard pipe that it had been earlier, but it certainly wasn't soft either. She reached down and grabbed it with one hand and slowly slid the condom off. It was full of my cum and she took it by the tip, laid down on her back right next to me and held it over her open mouth. I watched my thick creamy load drip out of it into her mouth. This woman was unbelievable. She could of just told me something sexual, or asked me a sexual question and my dick would have been at attention for her, but she let my semen slowly drip into her mouth and she seemed to enjoy every drop more then the previous.

    Then she sat up and said, "I need to save some of this", as she placed the condom between my legs and went back over to the dresser where she pulled out more ropes. She wrapped one around each of my ankles and said, "Now I'm going to play with your asshole."

    I panicked. I started looking around the room to make sure there were no big dildos or anything. I think she could tell that I was freaking out, cause she immediately said, "Don't worry. I'll be gentle and I'll stop if you tell me to", she went on, "Have you ever heard of a G-spot? Men can get intense orgasms from G-spot massage. I'm going to give you a G-spot massage to see if I can make you cum for me, without me touching your penis. Is that okay?"

    I felt a ton of relief. A "massage" sounded much better than a giant dildo. So with some reluctance, I said, "Yes, Mistress. That's okay."

    "Good", she said as she grabbed the rope around my left foot and tied it to the left bedpost on the headboard, then walked around the bed and did the same to the right. I was in such a compromising position now, and realized I couldn't do anything to stop her at this point. My hands and feet were both secured to the headboard, i was on my back with my ass rolled up in the air. She crawled onto the bed and took her position between my legs. She grabbed the condom and squeezed it out all over my cock and balls.

    "I need you to give me some more precum. I could have used your cum from the condom, but this is more fun, wouldn't you agree? Do you have more precum in there for me?", she asked as she slowly stroked my cock and played with my balls.

    "Yes Mistress. Anything for you.", I was really getting into this now.

    "OOOOOHHHHH GOOD BOY!", she said as I watched a big drop of precum spill out of my dick hole onto the index and middle finger of her right hand.

    "This is perfect. I am going to start your massage now, just relax."

    She dropped back between my legs and I felt her circle my asshole, that precum was slick. Then she slipped her middle finger into my ass. I tensed up and while rubbing my taint gently with her left hand, she assured me "Relax, you'll enjoy this".

    I took a deep breath and tried to relax.

    "Stroke your cock for me a little bit", she said.

    "I can't Mistress", I said. She started laughing and said, "That's right. I'll do it, but just for a minute".

    She moved her left hand from my taint to my cock and slowly started stroking and moving it around, and that's when it happened. We both knew it... she found my G spot. She immediately stopped stroking my cock and said, "I think I've found it. Now, I just want you to lay there and relax. I am going to give you an orgasm like you've never had."

    I was in shock, this woman had already done that, multiple times, and now, I was feeling something new and incredible.

    "You already have Mistress", I told her, "Everything you've done to me has been amazing."

    "Good. I don't want you to forget me, so just relax for me" she directed me, "I'm' not done with you yet".

    All while moving her middle finger inside me. I can't even describe the feeling. I had felt my balls had been completely drained of semen, but as she rubbed my G-spot, I could feel pressure building again. I was on my back with my butt curled up in the air, my cock began to stiffen and was again dripping precum, this time onto my own chest. She was kneeling between my legs, her left hand on the back of my right thigh, and the middle finger of her right hand reaching in and rubbing me. I could feel myself getting more and more excited and aroused.

    I was moaning without realizing it, because she began to ask me, "You like that, don't you. Your Mistress knows how to make you happy, doesn't she. Now, you know what Mistress wants, don't you?"

    I continued to moan, this was like nothing I had ever felt. I was in heaven.

    "Mistress wants your hot hard teenage cock cum. I want to watch you cum this time. I want to milk every last drop out of you without touching beautiful dick. Show me that cum baby."

    She knew how to talk to me. To this day, I love a woman who tells me what she wants like that. My cock was rock hard again, it was pointing at the headboard. I could still feel the pressure building, but didn't imagine there was anything left in there. There had been a couple times through high school where I thought I'd see how many times I could jack off in a day, and anything after 3 or 4, my ejaculation would become very small and just drip out.

    "I want to Mistress. I want to", I told her as I looked up at her.

    She looked like she was enjoying this as much as I was. She kept moving her finger, massaging me, "Let me see that load. I want to watch a load of hot cum spill out of your cock", she said. And that's when it happened.

    I squirted the biggest stream of cum that I ever had. The first spurt hit the headboard and splashed. Then the second spurt came and it shot up and hit my neck. It wasn't a small load, it was heavy and hot and I could feel it running down the right side of my neck and shoulder.

    "Oh yeah baby, that's it. Give me more, give it all to me", she told me without missing a beat, she just kept her finger moving on my G-spot. After the first 2 spurts, semen kept coming out, but it was just dripping.

    "That's a good boy. Give me all that cum", she said.

    And everytime she'd say something, a bigger drop would come out. I was dripping all over my abs, my cock still rock hard and just draining itself of semen. I was in shock. Where was it all coming from.

    "I'm going to milk every last drop out of you", she told me.

    "You are Mistress. Please don't stop".

    And she didn't stop, she rubbed my G-spot and drained me. The first spurts were about 2-3 seconds apart (the big ones), then it got to be 5 seconds or so, then 10 seconds, but she kept rubbing, and my cock kept dripping for her, then 20 seconds, then 30 seconds, but I kept cumming for her.

    "Remember", she said, "Every... Last.... Drop".

    "I think I'm almost done Mistress," I told her.

    At which point, she took her left hand, squeezed my balls and made her way up my shaft. Essentially milking my cock like you would a cow, squeezing tighter and tighter as her hand went up. And that was it, as her hand tightened around the tip of my dick, one more big drop of semen came streaming out. White, thick, long and stringy, it almost dripped all the way to my stomach before the strand broke. When that last drop landed on me, I was totally relaxed. So satisfied. I melted into the bed. She got up and walked to the headboard where she untied my hands and feet (leaving the ropes on me, just removing them from the headboard). She reached into the drawer and gave me a towel and asked, "How many orgasms have you had now? Four?"
     
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  4. realwrl

    realwrl Member

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    I replied, "Five." She turned and looked at me, "Five?".

    "Yes Mistress. Two in your mouth. Two in your vagina. And this last one." I explained to her.

    "Did I tell you that you could cum twice inside me?", She asked.

    "No, Mistress. I'm sorry. Should I have told you I was cumming again?", I asked her.

    "You're lucky I LOVE your cock. But yes, tell me when you are going to cum unless I tell you otherwise."

    "Yes Mistress", I said.

    "So FIVE orgasms? That should mean that you're good and ready now. Now it's my turn. I've had one orgasm, so you owe me 4. Clean yourself off with that towel and stroke yourself a little bit, then tell me when you're ready to fuck again."

    I think she could see my jaw drop. Here I was, a virgin up until this day and I had come here for a "job interview", and had ended up having the most amazing sex I could have ever imagined... and apparently, I was in for more. Wiping up all of my cum off myself, I sat there astonished that this hot woman had not only coaxed so much cum out of me already, but she wanted more too! Once I was mostly cleaned up, I took a little bit of cum from the towel into my right hand and began stroking my cock for her like she had requested. After the G-spot orgasm, I maintained a full erection. It was different than any orgasm I had ever given myself (as were all the orgasms that she had given me). I slowly stroked my cock using my own cum as lube, and rather than focusing on the tip like I normally would when jacking off, I stroked the entire length of my dick and rubbed my balls as well. She came back to the bedside, and I said, "I'm ready Mistress".

    "Good boy", she said, as she took the rope on my legs and tied each leg to each post on the footboard this time. She then took my hands and tied them back to the headboard where they had been previously, "I see you've kept your cock hard for me. Good boy", she smirked while straddling me, "I'm going to fuck myself silly using your dick. You need to keep it hard for me, and if you're going to cum, you NEED to tell me, but you should be able to keep up now that you've had FIVE orgasms. But before..." she slid herself back over me... I felt her wet cunt drag across my dick and I wanted to be inside her again, "But first a condom".

    She reached to the dresser, and grabbed a condom. She wiped the cum that I had rubbed on my dick and balls and put the condom on me. She then immediately straddled me and started bouncing up and down on my long hard shaft. She must have been very aroused, because I slid right in with now problem and she almost instantly had an orgasm.

    "That's one", she told me, "Good boy. You keep that cock nice and hard for Mistress." She then sat all the way down on it and began to grind on me like she had earlier. It started slowly and gradually picked up pace and intensity. She began to get louder and louder as she pressed and rubbed against me. I remember wishing that I could reach up and grab her tits, the thought of it made my cock throb and pulsate, but at this point, I wanted to get her off. I wanted to see her orgasm again and I finally got up the courage to say something.

    "Fuck that hard cock", I muttered.

    "What?", she asked.

    "Fuck that cock", I said again, "Make that cock yours!"

    At which point she began to orgasm. This one was different than both previous, she didn't squirt and it wasn't as small or as quick as the second one, her body began convulsing and she lifted herself off me a bit, and as soon as she pressed back down, she'd begin quivering again. Once that passed, she looked energized of all things and hungry for more.

    "That's two", she said (three total, but I still owed her two). Luckily, her deep grinding on me gave me a little time to recover. That wasn't as stimulating to the tip of my dick as deep thrusting tends to be. This was a good thing, because she then asked, "Are you ready to have your way with me?"

    She began untying me. I was stunned... I had never had sex... what would I do? And so I asked, "What do you mean Mistress? What should I do?"

    "You think I'm sexy right? I make you horny, don't I? Have you ever watched porno? Is there anything that you want to try? There must be something on your mind... some way that you'd like to fuck me. I'm yours right now. I'm your fuck toy. Just remember you need to make me cum 2 more times."

    I was baffled. Once again. She got all the ropes off of me and my imagination was running wild. My cock was throbbing with excitement again. "Well, do you know what you want?", she asked me.

    "Yes Mistress", I said, "Stay where you are, just bend over the bed." I stood up and took my position behind her. I guided my long hard cock into her warm wet pussy with my right hand. I slid it all the way in and she moaned as every inch penetrated her. I then grabbed her hips and began fucking her hard. Pulling her body against me like I had seen on porn. She was screaming and moaning, and I could tell the rhythm was sending me toward orgasm, so I decided to change position.

    "On your hands and knees", I told her, "You're getting fucked on the floor."

    She did as I asked and I took up my position behind her and pushed her head to the ground, "Head down, ass up", I said.

    My inner porn star had come out. Again, she did as I asked. Rather than getting on my knees behind her, I stayed on my feet and slid my cock into her soaking wet slit and again began fucking her, this time at a downward angle. By her moans, I guessed that she'd be cumming again soon, and she did.

    "FUCK ME! FUCK ME! FUCK ME!", she screamed at me. And I did. Hard and deep. She then reached back and slowed me down with her hand. "That's 3. You only owe me one more, and I have a special request for this one", she said.

    "What is that Mistress," I asked her. "I want you to fuck me in the ass. I want you to make me cum with that big horse dick of yours up my ass."

    "Okay, but before I do that, get on the bed, on your back and spread your legs for me." I was dripping sweat and tired from all the thrusting, but I wanted to fuck her while looking at her. I wanted to see her titties bounce. I wanted to see her face as she orgasmed. I wanted to fuck her face to face.

    She agreed and slowly crawled onto the bed. She rolled onto her back and said, "Remember, I have a request. You DO NOT cum until you fulfill my request."

    I agreed and took my position between her legs and thrust my cock deep into her. Her back arced and her tits looked perfect, so big, so round, so soft. I took one into my hand and leaned down and sucked it. I sucked it hard and she moaned. I continued thrusting into her as I moved over to her other breast and did the same, pulled it toward my mouth then opened up and sucked it. I sucked hard and deep. She was moaning so heavily at this point. I sat up and started fucking her fast. I don't think I could have moved any faster. Hard, fast, deep, our bodies were slamming into one another. Her big tits were bouncing all over and she was moaning deeper and deeper, then she came. Her body tensed up and her pussy began to secrete a heavy white cream all over my cock. After this orgasm, she laid there silent for a minute. We were even. I wanted more. And she still had her request, but I was afraid I had done too much and she was now tired. Boy was I wrong about that. She had the sex drive of a teenage boy... Thank god!

    "That was great, honey. Now you owe me an anal orgasm. This is the only time I'll let you use lubricant", she said while turning over and pointing at the dresser. "Get a new condom and get some lube. I want to feel that cock buried deep inside my asshole." She took her hands and knees, and said "Hands and knees, right?", with a smirk.

    At that moment, I realized I had gotten a little too big for my britches for a moment. She had always been in control, but let me have a moment where I thought I was the one running the show. I removed the condom that I had on and was shocked to find it full of precum. The amount of cum and precum that had oozed out of my cock today was miraculous.

    "Dry that cock off", she said, "My asshole is nice and tight." I wiped my dick on her comforter and began to put the new condom on. After fumbling with it for a minute, she turned around and did it for me.

    "You’re going to have to learn how to do that quicker. Now, take some lube and put a finger in my ass", she told me.

    I did. I drizzled lube in her ass crack and slowly slid a finger in. I moved it in and out a bit, then she said, "Put another in. You need to open my tight little asshole up if you're going to fit your massive cock in there."

    "Yes Mistress," I replied.

    Hearing her say I have a massive cock made it throb even more, I could feel the condom tighten around it. I fingered her ass with 2 fingers, then she said, "Put in a finger from the other hand."

    I pulled my first two out a bit, then I slid all 3 in together. I moved them in and out together and then began to alternate. She seemed to enjoy it for a minute, then she told me to put two in from each hand. I couldn't believe this was happening. I put my index and middle finger from my left and right hand right at the entrance of her asshole and slowly pressed. Her asshole opened up and took them all. I played with it a bit, then she said to me, "Stretch it".

    So I began pulling my hands apart with my fingers deep inside. I kept them moving in and out slowly as I stretched her asshole. She asked me, "Do you think you can fit that big fuckpole of a cock in there now?"
     
  5. realwrl

    realwrl Member

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    Continued

    I replied, "I think so Mistress."

    "Good”, she said, “leave two fingers in there, turn your palm up and pour some more oil on me. I want it to go in. I want to make sure you don't have any problems getting your big horse dick in there."

    I did as she asked. My cock was throbbing. She had the nicest ass. Playing with oil? Another first, and a huge turn on. Honestly, I didn't know if my cock would fit in, then she said, "That's good. I want to feel you inside me. Put your dick in my ass and fuck it."

    I put the oil down and pulled my fingers out. Her pretty little asshole closed up and a little drop of oil ran out and streamed over her wet, pink pussy. I knelt behind her and with the thumb of my right hand on the top of my cock tip, I began to press my big hard cock into her. Little by little, her asshole opened up until my entire tip was finally in.

    "GOD! You're stretching that little asshole", she said, "Now get the rest in there and fuck me."

    At this point, I was ready, "Yes Mistress", I told her and I continued to direct my cock into her asshole with my right hand.

    I remember her almost squealing as I pressed deeper and deeper, "FUCK FUCK FUCK FUCK FUCK FUCK." It was barely audible, so I asked if she was okay.

    "You get the rest of that dick in me and you fuck me with it."

    Okay, she was fine. I continued to press it in. Deeper and deeper until I finally felt my body against hers. Time to fuck. I began to pull back and realized how extremely tight her ass was. It was like jerking off dry. I could feel the skin of my cock pulling over the tip, so continued to slowly pull and began adding lube for the next few in and out strokes. In and out, in and out. It was slow, but it felt SO GOOD. She agreed, she got louder and louder, "Yes, like that. Fuck that asshole. Feed that asshole your big fat cock."

    Her dirty talk turned me on and caused me to increase my tempo. I then went from my knees to my feet and she just about screamed, "YES!"

    Once on my feet, I really started driving my cock into her asshole and I could tell she was enjoying it. "I want to see your face as you cum Mistress. Can you roll over and let me pin your legs back?"

    She was apparently all for this because she pulled herself off of my cock and laid on her back and held her legs for me, "Get that cock back in my asshole".

    I knelt in front of her again and stuffed my cock back into her. I grabbed her ankles and pinned them to the bed next to her head. I started fucking her ass so hard and so deep. She was moaning and screaming and began to breath like she was cumming, "YES, YES, YES", she exclaimed, "Keep going, don't stop".

    I kept fucking her and she began playing with her clit. She immediately started squirting and moaning and screaming more and more. "FUCK YES", she yelled, "Cum for me again. I want you to cum for me again. I want to taste it."

    That sent me over the edge and I told her, "I'm going to cum Mistress".

    She kicked me off of her and pushed me onto my back. With one quick motion, she rolled my condom off my dick and took my deep into her mouth. Both of her hands were reaching up and pinning my chest down, her head bobbed on my cock slightly and I could feel her tongue against my balls. How she took my entire cock is still a mystery to me, but she did and it felt incredible. I began to cum again. With each pulsing load that I shot, I could hear her moan. Her moans turned me on and coaxed me into creating more semen for her to swallow. She sucked my dick like it was a the straw for a thick milkshake. Each load feeling better than the last. When she had finally drained my cock again, she sat up and said, "I like you. Let's get some lunch and finish this discussion about the web designer position."

    Wow. Just like that? No talk of what just happened? We got dressed and she led me to her kitchen, where her husband was making lunch. I thought I was going to get shot, but we all sat down and ate lunch. She asked me to put a resume and demo disk together for her based on what she had showed me and that we'd be in touch.


    So anyways, she asked how I was in the email I got today, and asked if we could get together sometime. I did a little snooping on social media and learned that she has moved to a neighboring city (divorced from her husband). So my question... I haven't replied yet... should I? She still looks pretty good from what I can tell, but this was 15 years ago.
     
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  6. wolfhorny

    wolfhorny Member

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    Go on, she sounds like fun!
     
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  7. realwrl

    realwrl Member

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    Well.... that's one vote yes.

    I'm guessing she's mid 40's now. I'm in my 30's.... If time has treated her well, it could be a really good time. My biggest reservation is that she was SO AMAZING the first time (maybe because it was my first time). I don't want that memory to be deflated.
     
  8. AGFUNK

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    That was awesome. Why would you even question seeing her again? Just go do her!
     
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  9. CaramelLady

    Guest

    I do not think anything will detract from that memory. What happened, happened. What can change that? Your first time appeared to be mind blowing and you will never duplicate that.

    But you do not want to duplicate what happened. You want to make an entirely new memory from a new experience. You were in a student-teacher relationship. You are now both equals.

    Go show her what the student has learned.
     
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  10. ThumbUp

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    Give me her email :D
     
  11. Alwayslearningsex

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    and mine too

    sounds so good, it got me hard
     
  12. Ellsworth5

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    A very enjoyable read, thanks
     
  13. _Acid

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    Do it