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My name is Jack, and man I have a wild story! Let me give you a brief back story before I begin to take you down my latest sexual journey. My girlfriend Kelly, well more like long distance girlfriend because I recently had to move due to my job changing location. See, we never lived together and she let me fuck basically any girl I wanted. She usually got all of my bedroom attention though because I worked alot of hours. She was great at everything and I should’ve just claimed her but we had a good thing going.

Anyways, I moved so quickly that she couldn’t afford to quit her job and go with me. We did talk though on the phone and computer, usually late nights ending with intimate sex chats. One night, she told me she rented a porno and they gave her an all lesbian one by mistake. I asked her if she was going to watch it anyways, to which her response was a hell yes. I asked her if there were any strapons and she decided to check it out for me.

A few minutes later and she informed me yes. I told her that it was hot when two women could get off like that, even betting her that the one being the man was probably cumming her pants. She got quiet for a few moments, all I could hear was some of her video playing in the background. Suddenly she says, “Holy shit, I’d eat that!” I didn’t know what was happening or exactly the scenario she saw but she tells me all of a sudden what she wants for Christmas.

I laughed and said, “A strapon, really?!” She laughed back that I sounded too overly excited. I told her that if she was serious, Santa wouldn’t necessarily have to wait until Christmas. We were planning on getting together soon and I knew now a gift that I could give her.

The conversation kept going about the porn that she was apparently still watching. She told me that she could see herself fucking another girl like that and the same in return, but she would have to have the real thing. I told her that what she said made my cock beg for attention and started stroking it.

I told her that I would love to watch her plow into another woman. I described how my cock was already throbbing so hard that it felt like it was going to split. I said, “You bending some bitch over and making her moan while your hammering into her, God that would fuel both of our desires. I think it would be so intense!” She told me she agreed and had started fingering herself.

I explained, “I’m going to sit in the corner and jack off like I am right now.”

She started breathing harder.

“When you see me with my dick getting hard by watching you, you will start fucking her harder, making her juices flow down her leg.”

“More,” moaned Kelly.

“Your pussy is going to start throbbing and your going to squirt while you pump her ferociously. You both will come at the same time and beg me to bring this big hard cock over when you get your breath back.”

Kelly came on cue and I did too. She told me that she just had one of the best orgasms that she can remember. I was so turned on by this that my dick didn’t go limp. I told her I still had a nut and she said she promised to take care of it next time she sees me when she comes to visit. I really wanted to take care of myself again but something told me just to edge it.


I woke up the next day with a massive hard-on that was feeling very sensitive. It tingled to the point of almost hurting and made me stiff all morning getting ready for work. I didn’t have time to rub one out so I just left him be and went along my day.

I had been at my new job for about 4 months and had gotten to know my duties and my co-workers a bit. One lady, no I’ll just say cougar, named Tanya worked right beside me every day. We had gotten to know all about each other’s lives through all day conversations.

She knew I had a long distance relationship and compared it to internet dating. She had a great sense of humor and we joked back and forth from day one. She even made comment once about how it feels to have a virtual hand job from cyber space. I would respond back, it flirting, “that i heard cougars give paw jobs that are amazing.” She would blush but always insist I was too young for her.

There was only a thirteen year difference between us so it wasn’t totally unbelievable, still she would scoff at the idea of me being her cub. Sometimes, we worked twelve to sixteen hrs, six and seven days a week, so naturally our convos would taper around sex quite often. It was like a challenge to see who could get the other one’s goad that day. Needless to say she always got the upper hand, creating some sexual tension for me, on top of what I already had.

Anyways this morning my cock would not stop, I could not control him. She must have noticed too because she didn’t talk much that day, but I caught her staring once in a while. I must admit that catching her eyes wonder like they did really didn’t help my cause.

I started to think about how to approach her and nerves suddenly izmit escort started kicking in. Not the good kind of nerves that feed off of adrenaline either but the kind of nerves that emit from fear. As I contemplated on what to say or how to approach her, my composure sank, worries of rejection and humility took its place. Did I fear her dominance, no…at this point I think I rather welcomed it.

I must’ve been too busy being concerned that my hard-on quickly went away and sadness was the look on my face. I didn’t realize it at the time but I was starting to feel intimidated by this lovely cougar before me. There really wasn’t anything for me to be shy over, she had said filthier things to me than I ever came up with for her.

She recognized my change in demeanor and came over to ask me if I was ok. I said that I was conflicted and didn’t know how to say it. She asked me not to be a wimp and just say it. I looked down at her feet then back up to her eyes, finally I just took a deep breath and said it.

“My girlfriend wants to have a threesome with me, she wants me to buy her a strapon, and I want to watch her fuck your brains out even if all I can do is watch.” There it was out, now all I could do is wait to get my usual rejection.

She looked down at my cock, half starting to swell again. She told me she knew I was serious because my cock had been hard all morning and she would giggle to herself when she thought I wasn’t looking. She also knew I caught her and laughed at my nervousness. She licked her lips, still staring at my cock, and told me she giggles when she cums. Then she let out another playful giggle.

I was stunned once again by this lavish cougar standing right before me. She tells me that she’s always wanted to fuck a woman just one time, like a man, but never had anything near that experience. I asked her if she had ever been with a woman before. She said no, not even an interest in having her pussy ate by one, but maybe now….might consider it with the right circumstances.

She said, “Fuck it cubby boy, you want to see me get fucked by your girlfriend and then watch her eat my drippy wet pussy? Show me how swollen your cock is right now.” She looks around as she tells me to go ahead the coast is clear.

Like some kind of spell put over me, I dropped trouser without any hesitation whatsoever. Not even a concern to double check to see if she was lying. There I stood exposing myself without trepidation of getting fired or losing my livelihood over such a trivial action.

She only made one comment, “Damn.” How was I supposed to take that. I looked flush. She knew it, she had my goad for the day. She asked me when my internet handjob was planning on coming over for such an excursion. I told her in two weeks when we finally had a free two day weekend.

She told me, she’s going to consider it but I have to reach a few demands first. I knew she was wicked and this could be torture but I said yes to her anyways. I didn’t even know what I was getting myself into or if they would even end up going through with it, but I kind of liked the way she became assertive.

Her first demand was to see the strapon live and not from some picture. I told her I hadn’t bought one yet, a smirk came to her face. She said for me to buy two then, just to let her know I was serious. I was so turned on at that moment that I was willing to by one in every size just to make sure. I asked, “How big?” She answered, “The same size as you or bigger.” I was about eight and half with some girth so I knew what I was looking for.


When I went home that day, it hit me, I forgot to ask her where the adult store was located. I frantically searched the internet to see if I could find overnight shipping. Finally, I searched and found the local porn shop, called “the right spot.” It was about to close in an hour so I had to hurry.

It was a half hour drive so I only had a half hour of shopping. I went straight to the counter where two young ladies were standing, that I apparently didn’t notice at first. The clerk was a middle aged women who could have been another cougar. She asks me if she could help me, to which I blurted out, “I need a strapon,” as I finally noticed the two girls who were now giggling at what I just said in front of them. “Two actually,” I tried to save myself from embarrassment.

The clerk, who’s name was Melanie, told the girls to excuse us and offered them to check out the lingerie. The girls giggled once more as they pardoned themselves towards the sexy undergarments. The giggles and the corsets were sending shivers down my spine and jolting my cock to life.

Melanie asked me what kind of strapon I was looking for. She knew her shit, plus made the conversation very comfortable and open. She explained that they had the more expensive kind, which was basically a harness with interchangeable penises. There were less expensive ones that were a harness with a dick but had vibrators kadıköy escort inside. There were strapless strapons that the woman places inside of her so both parties get penetration. Then there was the regular old standard harness with a strapon. She told me that most people get flesh colored for pussy play and unnatural colored for anal play.

I was quite overwhelmed to say the least, but I had to explain somehow to Milfanie about my possible future scenario. She had all this knowledge and what sounded like experience that I quickly warmed up to her. I just blurted it out that I had a lady friend who offered to have sex with another lady friend and I could watch but I had to first present a couple strapons. She seemed intrigued.

“You are buying these just for a mere chance, wow,” she exclaimed. “Do they know each other? Do they have any of the same interests? Are you allowed to jerk off?”

She had lots of questions and alot of them I hadn’t really considered except jerking off. I explained how Kelly was in the picture, what she said, and then told her how Tanya came into the picture with her demands. Melanie said something I really didn’t consider, she told me that it sounds like Tanya was secretly a dominatrix or at least wanted to be. She then deliberately turned me around to look at my ass.

“She’s definitely going to try and fuck you up your ass,” she add, “it’s cute and would look great bent over. I was getting turned on by her playfulness and by the fact that she was checking me out just as much as I was her. “I have had my ass played with before but nothing ever like this,” I admitted. “Hell, after watching them go at, I will be so turned on that I would be up for just about anything,” I revealed.

I picked out two regular basic strapons one flesh and one purple, then remembered that I had to get the size right or I could screw things up before they ever got started. I told Melanie that I had to buy it the same size as me, I knew about eight and a half inches but I wasn’t sure of the girth. She looked down at my crotch and noticed my bulge. She said, “Looks like he’s hard enough that we can judge right here, right now.”

I played deja vu in my head and just whipped it out right there. Melanie put her hand around my shaft, but she seemed to be doing more than measuring it’s circumference. She was actually starting to stroke me right in the store. She must’ve caught ahold of herself because she squeezed the head until a big glob of precum oozed slowly down onto her hand and her eyes never left my cock until she put her hand up to her mouth and licked it off. She stared me right in the eyes with a seductive look and gave me a half ass apology. I was lost in a gaze of lust and all I could asked her was what size lingerie would she be in.

We both decided on the right size and I started to make my purchases. I stopped her for a second and decided to go ahead and grab two of the strapless ones as well. I walked directly into the lingerie department and picked out purple matching garter, thigh high, and crotchless panties. I thanked Melanie for everything, especially helping me find the right measurements. She told me not to worry about it, as long as I wasn’t embarrassed, it was her privilege to help me. She licked her lips, then she gave me her cellphone number, and told me anytime I needed help to call her.

When I got home, I immediately got in touch with Kelly. I was so turned on that I told her to video chat with me, that way I could masterbate for her right on camera. The conversation started slow with the usual how you doing, how you been. I made the transition to sex when I asked her if she been a good girl for Santa. She told me she should be on the naughty list, she said she knew it wasn’t right but she couldn’t stop thinking about fucking another woman with me watching. I told her that I couldn’t stop thinking about it either and was trying desperately to find and make arrangements.

She wanted to see me cum for her and I was already happy to oblige. Within minutes, I jerked off and came all over myself, causing her to squirt one hell of a nut. She must’ve been really worked up because she couldn’t stop cumming for what seemed like ten minutes. I asked her if it was ok for me to find the right woman for the situation, she told me she was conflicted but she also wouldn’t lie about having these new fantasies going wild inside her mind. She was simply exited and told me she trusted me. We called it a night and I went to bed also with many perverted visions in my head.


The next day, I knew from the previous day that Tanya would want to see the proof, so I managed to pack the new toys in a bag that just seemed like part of my lunch. When I got to work, she immediately rushed over to me and I gave her a wink. She asked me if I had met her first demand yet. I looked around and saw that it was clear, then threw her the bag. She looked inside kahramanmaraş escort and her eyes peered real wide. I could tell she was turned on and probably wet.

She said, “I’m really surprised that you worked so fast acquiring these, good boy!” She told me that my quick response fascinated her and that she was now willing to participate if I could meet two more minor demands. The first was always to address her as Miss Tanya at work and Madame anytime no one was around. I knew right then and there that she liked being in control and confirmed to me what Melanie had suggested. I agreed to her next term with a flirtatious smirk. She then told me the final task, which was to simply meet this so called Kelly so she knew that I really wasn’t bullshitting her.

I stopped her right in her tracks with what I said next. I said, “I agree to your terms but I suspect that you’re a dominatrix and two can play that game. If you want to meet Kelly you’ll have to come over and perform on camera for her. Also, if anybody gets to fuck me in the ass, Kelly gets to go first.” Tanya just stood there with her mouth wide open. I had gotten her goad for once.

She told me that she was impressed with my aggressiveness and agreed to follow me home. All day at work I had a massive hard-on just thinking about what I was going to do to Tanya that evening. The thought of Kelly watching only increased my libido. I took a couple opportunities to flash my swollen dick at her just to assure her goad was mine for the day.

The workday went by extremely quick and it was time to head home for the night’s activities. Before we left, I walked Tanya out to her car and I opened the door for her. She asked me what exactly did I have in store for her. I grinned and asked her if she planned on staying the night. She told me she didn’t plan on it and explained that she didn’t even bring any extra clothes.

I told her that she could stay if she wanted and she could wear my bathrobe of needed, but for now I would allow her to follow me. I started walking towards my car and stopped to walk back to tell her one more thing. “Yesterday when I bought those strapons, Milfanie the store cougar, measured my girth with her bare hand. When I precame from her squeezing the tip, she just licked it off and told me to have a good time with you two. Tonight, I think you can give Kelly a really good pre-show of what’s to cum,” I teased. Leaving her with that thought of how I just asserted my dominance, I went back to my car grinning and headed home.


We arrived at my house and I helped Tanya out of her vehicle and held her arm as I walked her to my door. I let her in first as I flipped on the lights of the kitchen. She told me it was a quaint little place as I took off her jacket and pulled out a stool for her to sit on. I asked her if she wanted anything to eat but she told me maybe later. Then I asked her if she wanted anything to drink, out of everything I offered her she settled for wine.

As she sipped, we talked about music so I slipped in some Skynard and starting lightly massaging her shoulders. She seemed to be enjoying herself as she asked me to pour her a second glass. After a minute or so of soothing her, I told her to excuse me for a few moments and went to grab my laptop.

I got in chat with Kelly and gave her a quick warning. “Honey,” I said, “If you were serious about me watching you fuck another woman, you’re going to have to watch her get me off right now first. She gasped and didn’t really say anything. I didn’t want to give up my dominance but I did allow her to “stop this slut from getting me off” if at any time Kelly felt uncomfortable. They both must’ve liked me talking dirty and being aggressive because Kelly simply knodded her head and soon Tanya was down on her knees slurping.

Tanya was really good too, she licked my balls first while she worked my shaft with her hand. Her mouth was watering so much that when she steered her attention on my throbbing cock helmet, my nuts were just covered in the sloppiness of her drool. I loved every bit of it. Next, she squeezed seepage out while licking, sucking and slurping it hungrily.

As she cupped my balls and delivered my cock directly into her throat, Kelly let out a moan and squirted right at the camera. It took everything in me not to just explode right there. I had to make Tanya stop and take off her panties and bra to model for Kelly. I put three fingers into Tanya as I made her bend over to show off her beautiful ass.

I pulled out my fingers and licked them just to tease Kelly, making her go wild. She beat off madly as I spread Tanya’s luscious ass cheeks. We watched her pucker, then goosebumps started trickling across her rump. The sight was so amazing I started licking her from top to bottom and all around. Kelly told me she loved watching me eat her ass out and pumped herself harder. Soon, she let out an, “OH FUCK, I’M CUMMING, I’M CUMMING, OH HERE I CUM!”

I couldn’t hold back any longer, I put three fingers back in Tanya’s muff, then a fourth finger, and finally worked in my thumb. It had stretched magnificently to accommodate my hand and soon I had fisted her to squirt too. She convulsed only for a brief second before I had her on her knees swallowing my load.

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