My Seduction by An Older Woman Ch. 05

After my last interaction with Shannon and Danielle things around the condo got pretty quiet. It looked like Danielle was dating someone so played it pretty cool with me when she saw me although there was a little smirk on her face as she passed by me.

Shannon was also pretty busy and either totally ignored me or interacted with a business manner. I was perplexed by this and started to wonder if I had done something wrong. I could have taken these changes in behavior from both of them as a reason to be relieved and move on with my life but no, apparently I was disappointed by their aloofness and craved their attention and of course their approval.

I would go home and think about getting back into socializing with my friends and maybe even dating but after smoking a joint, would start fantasizing about being taken advantage of by Shannon, Danielle or in fact any mature women. I trolled porn sites looking for Cougers who made younger men their sex toys with little regard for the man's needs or wants.

I did try again dating women my own age but they all wanted me to be demonstrative, take the lead and just be someone that I wasn't. This went on for a few weeks when I received a text from Shannon saying that she would be needing some "things" fixed around the condo and could I come over this Saturday, late afternoon, say 4pm.

I immediately texted back that yes I would be there. It was only Wednesday and was excited, turned on and not sure how I was going to wait three days. My go to is to imagine Shannon commanding me to satisfy her sexual needs and jerk off and was about to get into that zone when another text came in from her.

" I expect my 'helper' to be top condition when Saturday arrives, so you are not permitted to touch yourself in any way that provides you with a sexual outlet!" she texted. While in this state of sexual excitement, I was of course disappointed and frustrated but I decided that I could tease myself without cumming although admittedly wasn't confident I could stop. Nonetheless, my cock was already hard.

I got busy with made up chores and tried to distract myself and one day saw Shannon sauntering down the court yard looking as hot as usual and was excited to see her but she pretended I did not exist and walked by giving me a sideways glance with a contemptable smirk on her face as she headed for her condo.

I was desperate for some attention from her and it was only Thursday. The next day the same thing happened with Danielle and I thought I was losing my mind.

I was getting crazy so I waited until dark and snuck around the back of Shannon's condo and was peeping into her windows. I could only see into her living room on the main but she came around the corner dressed in a sheer house coat and curled up in a chair with a glass of wine and a phone in her hand. Clearly she had nothing on underneath as it was a scanty looking apres' shower garment and her ample breasts were on full display.

My dick was rock hard and my hand went to it automatically and started stroking as she moved in her chair offering glimpses of her breasts and occasionally even her pussy.

All of a sudden this monster of a man walked into the room... naked and with a huge "semi", and oh man was he ever black. He looks like a football player.

He stands in front of Shannon with his hands behind his back while she is sitting in her chair sipping a glass of wine. She sits up and runs her finger over his ever hardening cock and looks up at him with a smile on her face and says something to him prior to opening her mouth wide and engulfing his cock.

My cock was rock hard and dripping wet as I took it out of my pants and stroked.

Shannon was fucking amazing and stroked his cock and played with his balls with her hands as her mouth was impaled on the largest cock I had ever seen. I couldn't stop looking at it.

She pulled off his cock and instructed him to stroke himself while she played with her pussy and watched.

It was weird in that I couldn't decide what turned me on more watching Shannon play with herself or this big black football player type stroke his monster cock.

All I know is that I was not going to be able to stop and then I heard this guy yell "What the hell are you doing lurking around?" from a couple of backyards away.

Thank god he couldn't see what I was doing but I took off as fast as I could and knew a quick private way to get back to my condo without being seen. Good way to get rid of a 'hard on' I would say.

As I caught my breath in my condo, I reflected on what I had just witnessed, my reaction to it and that Shannon had commanded me to not sexually satisfy myself. Probably best not to smoke a doobie then and tried to sleep in spite of all these thoughts going through my brain.

Thank god tomorrow is Friday, one more day to get through.

Somehow I got through the day and night staying busy with condo repairs and rent collecting.

I showed up at Shannon's on time and knocked on her door. Through the door she told me to strip and knock again when I was completely undressed.

After a moments hesitation and a quick look around, I stripped quickly and knocked on her door. It seemed like forever that she kept me waiting until the door finally opened and she ushered me in.

She turned and said to follow her upstairs. She was wearing a short skirt with a cut off t-shirt that just covered her breasts. I was getting a hard on walking behind her up the stairs and by the time we got to her bedroom I was fully erect.

She turned around and looked me up and down and smiled.

"Here are your clothes for tonight." she said and handed me incredibly short shorts and a t-shirt that was obviously too small.

"I am entertaining some friends tonight and you are to be our waiter. You will of course get them what ever they want and address them with a yes Miss or yes sir and of course me as mistress."

I was taken aback by the reference to "sir" and asked if there were men attending.

"There will be one man attending, yes. Is that a problem for you? " she smirked.

"Ah, no I guess not... mistress, but is he someone from the condo complex? " I asked meekly.

" No he is not but I can't guarantee that you won't recognize other people so you better be on your best behavior." she laughed.

"Now get dressed and start paying attention to my pussy before our guests arrive." she said as she laid back on the bed and opened her legs to offer me access to her bare pussy.

I had great difficulty getting the shorts over my hard cock as it could not be completely covered but I dove into her pussy and ate her like a starving man and she talked to me about how I was her pussyboy and had better make her proud tonight, as she pulled my head into her pussy an humped my face. I loved how she ground her pussy into my face after I teased her engorged clit with my tongue and she ordered me to get my tongue into her pussy.

Occasionally she would move her pelvis so much that I was licking her ass and she would moan and pull my head in further. My cock was never harder when she did this.

She came fast and soaked me with her juices and told me to go clean up and report downstairs to assist with setting everything up.

While we were getting things ready she would slap my ass or stroke my cock and whisper into my ear that I was to look at this evening as my next level training in how to properly serve one's mistress. I was both excited and scared about what she had planned.

People started arriving, well by people I mean several women of various shapes and sizes and most of them considerably older that me, a couple of whom I had seen around the condo complex at a distance. They all commented on my attire and lovely body while also ordering a drink to be delivered to them.

Jackie introduced herself to me as she walked in first. She looked to be late forties, overweight but strangely all in proportion so big hips and ass and pendulous breasts. She was a brunette with a short bob cut and piercing hazel eyes and fairly attractive really in a summer dress that exposed her best parts. She gave me the once over and smirked while complimenting me on my attire and patted my on my ass as she clearly noticed my hard on.

As I brought her in, Shannon and Jackie hugged and Shannon told me to give them a little twirl as they commented on my nice ass and obvious boner. They laughed at my embarrasment and then ignored me while they chatted about other things, and at that moment the doorbell rang again. I could hear people talking so knew there was more than one at the door and sure enough there were two more women.

The short blond with beautiful blue eyes introduced herself as Jodie and was likely also at least late forties but was clearly into weight lifting and very athletically built. Nice breasts and not an ounce of fat but her best feature by far was her tight ass and muscular legs that she was showing off in very short shorts. She said "You must be daveyboy." as she too took in my fully exposed body and ran her hand over my cock as she walked by.

Her friend was Sherrie, an auburn redhead with green eyes, looking also younger than perhaps her late forty to possibly even early fifties. She has a short skirt on with a cut off T-shirt just below her braless breast and she too was in pretty good physical shape for her age and although her ass was disproportionately large for her size, it filled out her skirt nicely. She looked at me and said: "I have heard a lot about you Davey but I believe Shannon referred to you as her 'pussyboy' isn't that right daveyboy?"

"Yes miss that is my name from Mistress." I said as I glanced at Shannon who was smiling and mouthed the words "good boy" as she welcomed her two guests into the living room.

All of these women who were frankly at least twenty years older than me hooted about what a fun evening this was going to be.

Shannon introduced me as her personal assistant and that I was to respond to their requests, whatever they might be and everyone hooted and hollered could they be first.

"Calm down ladies, first I am providing some entertainment for you as promised." Shannon said and at that moment there was a knock at the door.

"Get the door pussyboy." she commanded.

As I already had a woody, and now it was poking up about the waistline of my shorts so I hesitated in following her command, not wanting to answer the door in my condition.

"Do it now pussyboy or you will do it without any clothes on." she commanded and slapped my ass.

I made my way to the door with great trepidation and opened the door to the huge black man, the same one I had witnessed while peeping into her window the other night. He smirked at me and walked into the room filled with a half a dozen cougar- like women.

Shannon introduced him as Mike and said he was going to offer an exotic dance for the women as he set up his speaker.

For the moment I was no longer of any interest to these women as he gyrated to his music and teased the women with his body that was quickly losing its clothing.

When he was down to his g-string like underwear they gasped at the size of the cock and in fact his whole body seemed to take over the room. Hands were on his ass, abs, and he grabbed one lady's hand and placed it on his cock and the look on her face was pure joy.

It wasn't long before he was swinging this monster cock in their faces and they were obliging with their mouths and hands.

As I was serving drinks they were doing the same to me. As Shannon was sitting smiling at the activity she called me over and told me to kneel at her feet. She then invited Mike over and he assumed the same position with his cock aimed at her face and his hands behind his back.

"Bring his cock to me pussyboy." she commanded me and smiled that evil smile.

I hesitated while staring at his cock and a chorus erupted from the other women saying: "Grab his cock pussboy." over and over.

I knew this was a critical decision point in my journey with Shannon and I was reluctantly aware that I was mesmerized by his cock and maybe even a little turned on. I had never considered this aspect of my sexuality before so I was pretty freaked out about it all.

"Pussyboy I am waiting and not for long." Shannon glared at me.

I reached out and grabbed his cock and pulled towards her mouth and she pulled my face in next to hers and and said: "Get a good close look daveyboy, because I thing you like this, don't you?"

"Yes Mistress." was all I could say since it didn't feel like a question coming from her and also my cock was stretching beyond the bounds of the tight short pants she had dressed me in and was plain for all to witness.

With that she started licking this huge black cock to the cheers of her guests and hands were pulling off my shorts and stroking my cock while other hands were pushing my face onto his cock and saying "Lick his cock daveyboy, show us how much you like it." as they hooted and laughed at me licking his cock.

I was pretty freaked as I had never touched another man's cock before and yet had been watching porn that I was fantasizing the women as my wife and who was involved another man while I was forced to watch.

Anyway, everyone seemed really interested in me doing this and Shannon pulled his cock out of her mouth and presented it to mine saying: " Suck his cock pussyboy; show us how it's done and we will suck your cock while you are at it." and multiple mouths were on my cock, balls and ass and others were on my nipples.

I was so overwhelmed by this explosion of sensations that his cock entering my mouth was almost incidental to me at first, but then became my focus and I gave in to the whole experience.

Shannon whispered into my ear: " Make him cum and to make sure he cums in your mouth pussboy. Show everyone that you will do anything you are told to do."

She was also licking his cock and balls and then leaned back, opening her legs and saying to me to put his cock into her pussy and then lick her clit and his cock and she grabbed me by my hair and pulled me into her as his cock entered her pussy.

The other women were loving this, cheering us on and wanting to be next while they stroked my cock.

It wasn't lock before he was reaching his climax and Shannon reluctantly pulled him out of her pussy and pushed my head down onto his cock as he spewed his spunk into my mouth so much that it was leaking out of my mouth but my mind was on the at least two tongues on my cock and balls while fingers were playing with my ass. I wasn't sure how I was going to stop from cumming at this pace.

Shannon made me lie down on the coffee table and lowered her pussy onto my face and said: "I still need to cum pussyboy so get at it with your cum filled mouth until I add mine to your mouth."

I heard the other women playing rock, paper, scizzors for who was going to get fucked by this black man next and Sherrie shrieked as she won the contest; then Jackie slid onto my already hardening cock and started fucking me and saying:

"Remember pussyboy, no cuming until you are given permission." and at that exact moment Shannon came on my face as she pulled my head into her pussy with both hands wrapped in my hair.

Once she rolled off of me Jodie slid her tight ass on my face and said:

"I have never imagined anyone licking my ass before so lick my ass pussyboy and take your time until I tell you to stop. I want the same treatment as Shannon got and nothing less." as she guided her tight butt over my mouth. I worked my tongue into her asshole and struggled to breath which to my relief she mercifully alternated with her pussy allowing me to catch a breath until she too climaxed on my face.

As she rolled off of me to take her turn on the black mans' cock, Sherrie knelt over top of my face smirking down at me and said:

"Well pussyboy, I understand you like just fucked pussy, so get busy as she lowered her dripping wet pussy onto my face, sliding it up and down as she held onto my head to give her leverage. I was really struggling not to cum while she was doing this partly because I loved it but also because Jackie was climaxing on my cock with her full weight bouncing at the same time Sherrie was using my face to get off.

It was not long before Sherrie finished on me and all these women seemed satiated for the moment and I was left lying on the coffee table, face soaked and my cock at attention.

Mike packed up his gear and bid everyone adieu as Shannon saw him to the door. I was getting up to leave as well when Shannon came back into the room and let me know that I could leave but only if I wore the "outfit" I started in all the way back to my place and they all took turns sucking my cock on the way out to make sure it was at full mast for the walk home.

As they all said their "goodbyes" and Shannon walked me to the door she me quite firmly that I should not go anywhere and be on standby for the next event that they would be planning and to check my inbox for a recording of this event for my pleasure, and theirs. When you watch it you may make yourself cum but only if you also record that, consume your own cum and send it to all of us with a thankyou for us allowing you to do so.

"Yes mistress." I said as I hurried home oblivious to my cum soaked face and cock sticking out the top of my shorts. I could hardly wait to watch the video.