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Role playing threesome

While a seasoned vet of many threesomes, I've always had a fantasy of being with a mother/daughter or at the least an experienced older lady and a younger lady with about a 20 year or so age difference. While that is probably very common, I also has a specific role play that I wanted to experience. In this scenario, I was auctioned off or some how in the employ of the older woman. Let's just call her what she is-- a cougar. The matriarch's daughter is sexually inexperienced and is about to venture out into the societal circles that her family participates. The mother has no doubt her daughter has experimented with sex, but she wants to ensure the young lady is instructed in the ways to confidently be with a man when the time is right.

I was fortunate to come across a sexy lady named Susan. We had crossed paths virtually on some dating apps. We had toyed with the idea of dating/hooking up, but things really didn't get serious. We each led busy lives and finding the time for a real relationship was something that we couldn't keep up. It also didn't help matters that we lived quite a few miles from each other, so a real life meet was impractical. Still, that didn't deter us from chatting, getting to know each other and sexting. We would video call each ever so often and have virtual sex.

Susan was the stereotypical cougar. She worked in real estate and constantly on the go. While I didn't pry too much, she was either divorced or separated never indicating a steady guy in her life. I got the impression she got around but who is to judge. She was in her early 40s and very attractive which she took full advantage of. She was about 5-6 with bleach blond hair and could rock a bikini. Probably 34D with a thin waist. She told me stories of going to clubs and getting hit on by guys in their 20s. She loved the attention but confided they were all bark and no bite as she still preferred gentleman in there 40s and 50s. She said experience went a long way with her. That was one of the things that attracted both of us.

On one of those chat sessions, Susan brought up the topic of sexual fantasies and role playing. She told me of her escapades of doing the boss/secretary or teacher/student fantasy. I shared several of the vanilla role plays I had done. Over the course of our conversation, which had me as hard as a rock, I explained to Susan that I am very creative when it comes to role playing and fantasies. I went into detail how I had written a complete script for one particular fantasy. I also told her about a play date with a gal that was CNC- an abduction fantasy that this girl really craved. Susan got excited about that. She said that she always wanted to do CNC but as the initiator and not the "victim". She said it turned her on to flip the roles with the gal in control. This got my wheels spinning.

Normally, I'm the dominant type in play, but also am a switch because being the sub is actually a freeing feeling in that I have no say. I've given up control and anticipating what comes next. I told Susan that some of my more deeper fantasies involve me being used as a boy toy. Susan asked if there was any particular fantasy I had in being a sub and "forced" to perform. That is when I hit Susan with my mother/daughter fantasy. I explained how I had the outline of a script in my mind. I went on saying the fantasy would never happen because finding a mother/daughter team would be disgusting to most. I did mention though I'd still want to do the fantasy even if the ladies were not technically mother and daughter. I pretty much shrugged it off as Susan and I moved on to discuss some more fantasies.

A couple of days went by when all of a sudden I get a call from Susan. It was very rare for us to call each other unless it was a precoordinated video call. This was just one of those ordinary calls, so when I saw her name pop up on the screen, I was confused but my mind started to wonder what was so urgent to call now. When I picked up, Susan was all giddy. She told me how much my fantasy excited her. She went on to say that she met a girl named Alexis while working. I think Susan said she was an assistant with another company but did business with her. Susan, not the bashful type and an excellent read of people, struck up a mundane conversation with Alexis that kinda planted seeds in Susan's head. Susan stated that at another business meeting Alexis confided with Susan about her break up with a boy friend. Susan said Alexis was looking for advise from another single lady on a next move. Susan gave Alexis the old get up back on the bike and keep riding speech. Susan told me that Alexis was attractive but lacked confidence when it came to the bedroom. Susan reminded me of my fantasy and asked if I would be interested if the chance ever came up. Of course I told Susan I'd be interested and started to put my mind back on that fantasy. I explained to Susan how we could make it work, and that if it was game on, I'd plan a trip to come to them.

About a week later, Susan and I were having one of our texting sessions when she said she talked to Alexis in general terms about helping her gain some confidence. Susan said Alexis would be comfortable with allowing Susan to plan something. I reminded Susan of the fantasy where she was the mom and Alexis would be the daughter. I also filled in some details for Susan to share with Alexis. Still I wasn't too high on the fact of this happening. Alexis is young and being asked to join in a threesome. I told Susan that she needed to be explicit with Alexis in how this would play out as Alexis was to be the key ingredient in this fantasy. Two days later, Susan called and said Alexis was in. She showed Alexis my pictures and some of the sexting we had done. Susan said Alexis was very interested in her role as she felt it would boost her confidence. I asked Susan for some details on Alexis. All I knew at this point is that she is young and attractive according to Susan. I also inquired as to when we could set the plan in motion.

Within the hour, I had all the 411 on Alexis. Susan sent me about a dozen photos of Alexis. All were tame but still revealing. Alexis was 22 and just finished her degree in business. She had just started her first job as an assistant at a loan processing firm. Alexis was about 5-4, 115 pounds, she was petite and had auburn hair. Susan told me some of her interests were gaming, music, and photography. She also mentioned that she had secretly been attracted to older men because of their maturity. Apparently, Alexis' ex was immature and didn't take life seriously or at least seriously enough for Alexis. The thought of all this got me hard and wanting time to speed up.

Susan said Alexis was looking forward to our fantasy and was curious if the two of us could talk on the phone. Reluctantly, I told Susan that would be a bad idea. The whole premise of the fantasy if for the daughter to come in all naive and innocent (as such could be expected). Susan relayed this to Alexis who from Susan's account fully understood.

Soon enough the day arrived and we all confirmed it was on. Now in my fantasy this would have been on a much grander scale with castles and dungeons and fountain, etc. Of course, though, you make due with what you have. I suppose a hotel suite would have to do. Before I arrived, I had Susan check into the hotel along with Alexis. They were supposed to be there when I arrived. My instructions for clothing were quite simple. Alexis was to be dressed in a modest way with a skirt and button down blouse. Susan was to be initially dressed in power suit worn by most executive women. I was dressed in business casual in the role of executive assistant to Susan. Susan was the CEO of a small, yet connected investment firm. Alexis was her daughter tagging along on the business trip and supposedly going to a dinner with her mother the next day where many influential and available men would be in attendance. Per instructions, Alexis was to be in the inner bedroom when I arrived so as I would not see her.

I arrived and announced my purpose to drop off the forms needing to be signed during the next day's meeting. Susan greeted me at the door and invited me in. She then announced the ulterior motives for my presence. She tells me I'm there to seduce her daughter and show her how to please a man. Susan went on to say this would be a demo-performance. In other words, Susan would go first while her daughter watched. She would be providing instructions for Alexis as I performed on Susan. This was said at a loud enough volume that Alexis could here in the next room. Susan then led me into the other room where she introduced Alexis to me. Susan then explained to Alexis then need for a young woman to learn how to respond to a man's body and take control. She said watch and learn. Susan excused herself to the bathroom for a few minutes.

Susan came out dressed in sexy lingerie and ordered me to stand up. She circled me like a vulture about to feed on a carcass. She took her time to smack my ass and rub my shoulders. She then turned to Alexis to explain that the first thing is to be in control as she slowly removed my clothes. I was standing there naked as Susan once again circled me but this time yanked on my throbbing cock that was already hard. She told Alexis that a dick was hers to play with and control. Not one to lose dominance did she ever stoop or kneel in front my cock. Instead, she just teased. Susan suggested that Alexis touch my cock and bring my pre-cum to her lips as a taste. Eventually Susan dropped to her knees and took me into her mouth in a perfunctory manner almost mechanical. She then said to Alexis that men love having their cock sucked. She explained a proper technique and stated that the importance of orally arousing the cock with lips, tongue and teeth. She said the goal was to tame and drain.

After the blow job demo, Susan stripped down naked and commanded me to massage her as she laid face down on the bed. Susan told Alexis that a man needs to explore his woman's body as massaged her. Susan then flipped over and I naturally started to passionately kiss her, lick her, play with her tits while exploring her body with my hands. Susan instructed Alexis that the female body is a temple needing to be worshipped. Slowly, Susan guides my head between her thighs and directs me to play with her pussy. I lick her inner thighs and carefully pull her lips apart as my tongue darts into her slit. As I'm doing this, Susan provides an anatomical lesson on how pussy should be eaten and tasted. I continue my oral exam with licking, fingering, sucking and nibbling all parts of her love box. After awhile, Susan's voice trails off as moans and muttering replace the cold, clinical discussion. By this point her whole pussy is swollen and my tongues is darting and teasing her clit. Ever so often, I gently bite on her clit. Instead of commands from a superior to a subordinate, she is now screaming in pleasure. Keep going, don't stop are intermeshed with moans and heavy breathing. All of a sudden, Susan shakes violently and lets out a guttural moan. She continues to shake for a few more seconds and has lost composure as she whispers oh my God that was fantastic. I kinda of collapse on her and deeply kiss her. This snaps her back into character. She chastises me be saying how dare I kiss her like that.

Susan commands that I stand up and once again circles me. She asks Alexis if she enjoyed what she just witnessed. Alexis eagerly said yes. Susan looks back at me like a dog on a leash and says that was adequate but she needs to test my skills further. She addresses Alexis and provide options on what should happen next. Alexis suggests several positions. Susan reminds her they don't have all day and that Alexis still has to use me to prove what she had learned. Susan then says the proper next step is to show female control and says mounting me will prove her dominance over me. I'm pushed to the bed as Susan climbs on top and slowly goes down on my manhood until it is all inside her. She leans over and teases me with her tits and rock hard nipples. I lean forward trying to get a taste, but Susan pushes me down saying I'm not worthy to suck on them yet. She then looks at Alexis and smiles. Susan enthusiastically slides up and down my cock as her pussy lips lock around my cock with each thrust. I can't take it any more and loose my load deep inside Susan. This is a moment I had been waiting quite some time for and the circumstances were definitely surreal. Susan finally collapses on me and says you earned this as she deeply kisses me and then lets me suckle her tits.

Susan returns to Alexis and says did you learn anything? Are you ready for your turn? I want to see if my daughter can take confident control of a man and be ready for when it happens in the real world. Alexis sheepishly says that she thinks she is ready. Susan walks over to her and kisses her on the forehead and says she knows Alexis is ready. Susan reassures her to remember what was shown and to also allow me to guide her on the next step of the journey. Susan, back in character, tells me to go clean up and as she wants me squeaky clean for her daughter. For good measure, Susan says to make sure I can last. I reassure both that given 15 minutes or so I would be more than ready,

I come out of the shower and all dried off. Susan then says that this time is going to be slightly different. Instead of Alexis circling me like some circus animal, Susan wants me to take the lead but in a mother-may-I approach. Susan explains that Alexis needs to provide permission for whatever I do. I comply as Susan suggests that Alexis stand up as I face her. I ask if I can kiss her. Alexis says no and that I need to earn it. I then remind Alexis that I am at a disadvantage standing naked and exposed while Alexis is fully clothed. Susan interjects and tells me to gently undress Alexis. I ask Alexis if this is what she wants. She eagerly agrees. I begin with running my hands through her hair and sniffing her freshness. I stop and stare into her eyes as I bring my lips close to hers. She reminds me not yet. I then slowly unbutton her blouse and untuck it from her skirt as I remove it. Alexis is standing there with a lacey bra that perfectly outline her perky breasts. I slowly unclasp her bra, slide the straps off, and cup her breasts as I fling the bra to the floor. I dare not ask to suck on them but the desire is strong. I soon find the zipper of her skirt and unzip as I gently pull it down. I then help her step out of the skirt as she is standing there topless with only a thong hiding her pussy. I ask Alexis how she feels. She tells me that she feels alive and in the moment. I then slowly pull down her thongs to reveal a bald pussy that I couldn't resists slipping a quick finger in to be met with a faint quiver. Alexis whispered I didn't say you could do that but it felt great.

I then grab her and pull her close enough that my throbbing cock is leaking pre-cum onto her thighs. I whisper if I can now kiss her. Alexis responded by grabbing my head and passionately kiss me. I feel her tongue trying to go down my throat. Alexis said she wanted to taste me. As she dropped to her knees. I asked if she was sure and reminded her that she was supposed to be in control. She looks up at me and quite firmly says she is in control as she takes my member into her mouth. She doesn't try to deep throat or anything like that. Alexis is more like teasing my tip while sucking my pre-cum. Silently I'm begging for her to go deeper, but Alexis is just toying with me. I finally ask if she is going to take all of me and if she wants my cum. Alexis playfully states I can cum when she is ready. She now changes her technique by pulling her mouth away and slowly jerks my shaft and then begins to lick my shaft while teasing my balls. Eventually, Alexis stops and says she wants a massage just like mom.

Alexis lays down as I repeat the massage from before, but this time Alexis is more receptive as she helps guide my hands especially when I get to her ass. She rises up inviting my hand to roam her pussy. I continue the back massage and then flip Alexis over. Once again, I stare into her eyes and bring my lips to hers. She whispered yes as we passionately kiss again. This time it was not a tonsillectomy like before. Instead our tongues darted and teased, I begin rubbing her shoulders as my mouth nibbles on her neck. I slowly work my tongue down her neck and to her chest, I ask if I can suck expecting to be shut down, but Alexis answered in the affirmative. I jumped at the opportunity to suckle, lick, and trace her breasts with my tongue. She shuttered when I gently bit on her nipples. Unlike Susan who played it cool and detached. Alexis was very receptive of my actions. I asked in a whisper if she trusted me and if I needed to keep asking permission. Alexis responded that I was hers and that I could continue until she said no.

With that I continued the licking as I reached her navel and licked and sucked on it. I continued down to her thighs. As I spread her legs, I could see her pussy glistening with moisture. Given the wetness, I slipped in fingers one at a time until three were insider as I finger fucked Alexis hot pussy. She started to respond with moans and groans. I pulled the fingers out and brought them to her lips. Alexis eagerly licked off her own love juices. I then returned to her love box and proceeded to eat her out. Alexis was sensitive and easily responsive. Her breath quickly increased. I felt multiple quivers from her thighs as they would tighten and then release from my head. Her moans and groans were muffled. I continued for a few more minutes. I then senses Alexis seize up. All her muscles contracted at once. My head felt like in a vice. Alexis slowly exhaled not with a loud exclamation but with a visceral yet distinct groan. She continued to shutter what seemed like 4 or 5 times before she finally caught herself. She sat up and yanked my head towards hers. This time Alexis initiated the kissing and started stroking my cock. Alexis. slyly remarked on how good her pussy juices tasted.

In that moment, the shy little girl who lacked confidence around men and how to please them disappeared. Susan winked at me as she had been watching all along. Now the bold one in control, Alexis demanded that I fuck her as she kept stroking my cock. It was more than that. Alexis told me she wanted and needed my cock in a more sensual tone. You could sense the confidence brim. Now, I was the silent one. No questions from me. Alexis then surprised both Susan and myself. She states that she wants me to make love to her. She didn't just want a fuck. She wanted the passion. I followed her lead. Since she was already laying down, I climbed on top of her. By this time, my cock was so wet and dripping. The precum was all over the both of us. I began to kiss her once again, but this was more sensual. It was not the high energy type of kiss. It was the slow boiling kind. We would gently bite our lips. We would hold them together for a long time. We would go at an increasing rate of kisses until I moved to her ears and began nibbling on them. Alexis returned the favor by biting/sucking on my neck of which the results were clearly visible the next day.

Without saying a word, Alexis guided me inside her. I took the time to slowly go in. Once inside, I just paused for a few seconds just to enjoy the feel of her pussy surrounding me. Alexis snapped me out of this mesmerizing experience when she whispered to fuck her. It wasn't one of those one off "fuck me" statements. It was more like a plea of desire. I then slowly began to pump her. I was sliding in and out. I grabbed her hips in order to pull her close so as to penetrate as deep as possible. I kept pumping as I felt my orgasm building. Alexis uttered two words-- inside me. We were sympatico once she uttered those words. On the next thrust, I came deep inside Alexis. I was spent as I collapsed on top of her. As I caught my breath in the afterglow, Alexis once again planted a sultry kiss on me. I laid there for what seemed like hours, but it was only a few moments. Susan walked over and kissed us and helped both of us to our feet.

Susan then briefly jumped back into character. She asked Alexis if she had learned anything while her stare at me put me in my place. Alexis replied yes. At that point, we all broke down in laughter. We each showered and decided to go to dinner. On the drive over, I asked Alexis if the experience was as she expected. She told me yes and no. She said that the fantasy was hot but she didn't think she would get into it that much. Alexis then said that I might have ruined it for her with guys her age and said my experience turned her on. Susan quickly interjected and told Alexis that nothing was ruined but that she had been exposed on how to gain experience and then use it. I explained to Alexis that a confident woman is a turn on for most guys. I said they might feel intimidated at first but will appreciate it in the end. Susan concurred and said there were plenty of guys who would enjoy knowing that she is experienced.

A couple of days later, I texted Susan to see how she was doing and if that fantasy was fun. Susan said it was hot and would like to do something like it again. She also told me Alexis loved the experience and was looking to find a guy to play with. I joking said there could always be round two but this time the two of you are my sluts.

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