Sassy Shelly, My Stepmom


"So what are you suggesting anyway?"

She hesitated and then replied to the person on the phone. "Oh, my, Arthur, you are a resourceful one, aren't you. Are you out of your mind!" she said. She had raised her voice but a bounce in it suggested not a trace of anger, just her normal playful banter with my Dad. I flopped down on the family room sofa and picked up a novel I had been reading. I didn't see the need to interrupt her phone call just to let her know I was home.

She listened for several seconds then continued as if the person on the other end of the phone simply didn't hear her the first time.

"Arthur. Wait, Arthur. Listen to me. He is not going to go for this. I had a silly little record going and it will be broken. It's not like Guinness is interested for crying out loud!" She laughed hard for a few seconds.

"Yeah, right!!!" Again she laughed hard, almost hysterically as my Dad made some kind of joke. "Mmmm hmmm.. Yeah, I guess so. Sort of, but that isn't the point, Arthur. You are nuts. Oh, you are just nuts! This isn't going to go over. I'm not going to even ask him."

She listened again. She didn't notice that I had come home or was in the next room. I had not intentionally overheard what she said and wasn't paying particular attention until the next few words.

"No, it was silly and Keech isn't going to do this. I'm surprised you would even bring this up."

"Mmm hmm. Yes, but believe me, I would have to be pretty tipped to bring it up anyway, with anyone, let alone him! Yes. Yes. OK, I love you, too, sweetie. OK, talk to you later."

Antoinette married my Dad when I was 20 and she was 42. In the next 4 years we developed a very good relationship. She was funny, and I liked her, but my Dad and Toni made a strange couple both in terms of looks and personality from the very beginning. My Dad was a successful attorney and did a great deal of pro bono work for charity. He was very good looking at 58 years old, and ran with the mover and shaker circuit for the most part. His idea of "informal dress" was a pair of Ralph Lauren khakis and a matching top without a tie.

My late mother, Madeline, had been the consummate hostess, graceful, beautiful, witty, and charming. On one of their excursions abroad to Africa, she contracted a virus which was unfortunately misdiagnosed for nearly 4 months. She passed away in my sophomore year of college and Dad was beside himself. They had had a wonderful, loving relationship and he was very lonely without her.

After 18 months or so, Dad had told how his friend Bill set him up with Toni on a blind date. Toni had worked for Bill for several years, so he felt it wasn't exactly as if she was a complete stranger. When they first met, she was probably about 140 pounds and even today she's at best 10 pounds less. On a 5 foot 6 inch frame she was a bit on the chunky side, nearly flat chested, and a little rough around the edges. She had dark brown hair and greenish grey eyes. Her most prominent feature on her face was her full lips which were really beautiful, but otherwise one of those faces that lacked distinction. I guess most people would say she is somewhat attractive, but certainly by no stretch was she a beauty.

I remember not long after they met and started dating that Toni would tell dirty jokes, make suggestive comments and just be "rough trade". The contrast to Madeline was striking, surprising, and almost alarming. Some of his friends and I wondered secretly if she had found him as a mark, marrying him to divorce him and take his money, that sort of paranoia.

We couldn't have been more wrong. Toni may well have been from the other side of the tracks but her loyalty and love for my Dad had been proven well beyond anyone's doubts. She simply adored him. The two of them were obviously very happy together and had what appeared to be a very good relationship.

To be certain she scrubbed up her dinnertime manners considerably over the past few years, mainly because Dad spent a great deal of time and money entertaining guests at our home. She embraced formal dining, entertaining etiquette, and other trappings of success with dignity and alacrity. She had transformed from what was most likely a barfly into a budding social butterfly.

Toni had developed excellent taste in furniture and decorating and had really done some amazing things to our house over time. She knew that Dad and I needed time to grieve the loss of Madeline and that changing certain things in the house would probably never happen. Dad and Madeline had been married for over 20 years, so she chose household updates with sensitivity and style.

In a supremely classy move, in fact, she had had a small portrait of my mother painted and framed by a well known artist and had hung it in my father's den on the wall as a Christmas present. I saw my Dad cry twice in my life; once when Madeline died and the day she opened the door for him to see that picture hanging on the wall. It was quite simply a beautiful thing for her to do.

Toni hung up the phone and came into the living room a few minutes later. When she saw me she flushed and said "How long have you been home?"

"Oh, I don't know. About 5 minutes or so. Hi Toni, how are you?" I teased.

"Hi honey. I'm sorry; I just am a little, uh, surprised to see you home so early and I didn't hear you come in."

"How's Dad?"

Her face turned almost beet red. "He's fine. Why?"

"Well, I thought I heard you on the phone, that's all. I thought I heard you say Arthur. Was that 'our' Arthur?"

"Yes! Yes, of course it was. He's fine. Oh, yes, he's just fine." Her red color deepened then began to slowly receded. I was wondering what the hell was wrong with her.

"Toni, are you OK?"

"Oh, yes, I'm fine, Keech." Keech had been my nickname for the past 10 years. I picked it up in middle school when a substitute teacher from India couldn't pronounce my name, Keith. Our English teacher was out for maternity leave and by the time she got back the entire football team, of which I was unfortunately a member, refused to call me anything other than Keech. True story, but I digress.

"OK, you just look a little flustered, that's all. I wasn't eavesdropping on your call, Toni, so if you guys are cooking up some surprise your secret is safe." Dad and Toni had developed a knack for "capers" as they called them. They'd do the goofiest things to each other and sometimes to me. One time they filled my entire car with ping pong balls just to fuck with me. Another time Dad took all of Toni's favorite shoes and replaced them with ones 2 sizes bigger. This went on constantly and they were good at it but if I could catch them discussing their plan sometimes I could prepare.

"You guys trying to pull a new caper on me? I guess you're about due for one. Or is it my turn?"

She laughed out loud a forced, fake laugh. "Oh, no. No caper planning in the works today, but watch yourself!", she yelled as she poked me in the ribs. "You never know!"

"You and Dad are worse than two teenagers." That was very true. They read an article, most likely an urban legend, about the college kids that sole a yard gnome and ran it around the country and brought it back with a photo album around its neck. The were so captivated by this dumb prank that they took our neighbor's lawn jockey and did the same thing, only the destination was Australia or Fiji or something. I didn't go on that trip but I suspect Toni engineered that one.

I relaxed on the sofa reading my book while Toni fixed herself a drink. It was about 4:00 PM and I asked her what was for dinner. She said that she didn't feel like cooking with Dad out of town.

"I thought he was coming back tonight?, I said.

"So did I. Now it looks like he'll be back in another 3 or 4 days."

That was somewhat unusual because my Dad hated to travel and when he did he had strict requirements for his departure and return. He was very, very meticulous about those details for some reason, especially since he and Toni were married. I just chalked it up to newlyweds not wanting to be away from each other and left it at that.

"Yes, it was an enormous disappointment to hear that he wasn't going to be back home tonight. I'd like to go out to dinner or have it delivered Keech. Maybe we can get Thai."

"Cool. Toni, next time you get a drink would you make me a 7 and 7?", I asked..

"Oh, my dear boy, but of course!" she replied in her funny voice. I loved it when she had a drink or two in her because she became much less inhibited and really let her hair down, especially when it was just the 3 of us.

I put down my book and we talked a while about what she was doing next to the house. They had redone the master bedroom about 2 years ago and were looking at architects for an addition possibly next year.

"How's the addition coming along?" I asked.

"It's going well" she said. "It's going to get expensive if we try to match the exterior of the house. Brick and stone masons aren't exactly as plentiful as they were 100 years ago. The foundation work and inside sketches are done. Want to see them?"

"Sure! Maybe I'll decide not to move out after all!"

Toni went into the den to get the drawings and spread them out on the floor. "We're thinking about an enclosed pool with an integrated hot tub. We'd love to get year round use out of it and it would be off the exercise room. I found a few companies that sell retractable systems which are just terrific. You can enclose or open the pool to the outside in a few minutes.

I noticed an area to the side of the pool, an extension from my bedroom. "Wow you guys are planning two expansions t o the house. This is really something."

"Yes, but Arthur and I have decided that we are staying here and honestly, Keech, it's as much for you as for us. If you decide that you want to stay here with us you know you are so welcome as long as you want to. We just love you so much."

She leaned over and kissed me on the cheek. Her perfume today was delicious, slightly sweet, not at all old lady-ish. Her lips felt full and warm as they pressed against my cheek. Instinctively I reached for the back of her head and pulled her lips harder to me.

"You two are so good to me", I said. "I try to do things around here but it seems like you both have it all figured out. Sometimes I feel like there's not much for me to add, and I feel that if I did stay much longer I might be overstaying my welcome."

"Keech we don't need you to help us. We want you to be happy, and if you need a few years here to get on your feet and work on your art then you should do it. That's why part of our expansion project is", and she suddenly was quiet.

"Is what?" I asked. I swiped our glasses and began to refill them with fresh drinks. "Is what is what is what!!!" I yelled like a little kid.

"It's something special. I'll let Arthur tell you. In the mean time, I'd like my drink, sir."

We had now downed 3 or 4 each in the last hour, so we were pretty buzzed.

"So you didn't hear much of our conversation, did you?"

"No. It sounded like the two of you were up to something, though. I can tell when you two are planning some sort of fun. What's up?"

"Oh, I can't believe I am even going to say this" Toni said under her breath.

"You, um, probably don't know as much about me as you may think you do."

"Hey that's always the way isn't it?"

"No, Keech, not like that. Do you remember how I met Arthur?"

"Yeah. Bill set you up on a blind date.

"It, um, wasn't exactly a date, and Bill doesn't exist. I was escorting Arthur. Yes, I was living in Las Vegas trying to make it on my own and my plans were coming apart at the seams. I had moved there with little money and it ran out fast. I wasn't a gambler, just normal life expenses were eating away at what I had. I decided to place an ad in an escort magazine. It was a last ditch effort to make it."

I was stunned, but more so by the thought of my Dad seeking the services of a prostitute than picturing Toni as a lady of the evening.

"I know what you're thinking. You're probably more surprised at your Dad than at me. But here's the big difference: Arthur was my first, but I wasn't his."

A chill filled me as she took a long drink and let the words hang in the air. My shock was clearly visible on my face.

She continued. "He called and I met him at a casino and we had a few drinks. I liked him. He took me up to his room, and in the immortal words of Jerry Seinfeld, yada yada yada, we got married." A big smile took over her face.

"We realized that night that we should be together. There were certain, 'signs', you might say, that indicated we were a perfect match. A month later I moved locally into an apartment and, of course, in with you after we got married. The important thing to remember here is that Arthur and I fell in love quickly and truly and nothing could change that."

"OK, you got me. Where are the cameras? Hi Dad!!!", I pointed at the mantle and ceiling. "Yep, Dad, this is one of your best ones yet!"

Toni looked at me with a rare seriousness. "Keech, there are no cameras. What I have told you is the truth. Do you want to hear more of what happened?"

"I think so. I need to know how my mother was replaced with a prostitute. That's something I am having a hard time picturing, Toni. You said it yourself. You were a call girl."

"Yes, but in the Pretty Woman sense!" she laughed. "I didn't even know what to wear, what to say, or anything. I was a total rookie. He was my first but more importantly my last. It really was a lot like that movie. We even laugh about it sometimes."

I was beginning to see the hysterically funny side of this story. It was just so hard to picture my Dad, uptight Arthur, picking up call girls, let alone marrying one. It's just so bizarre, I thought, but then again, who am I to judge?

"OK, Toni, I believe you that there are no cameras. I believe that you are telling the truth and that's great that the two of you found each other. I only have one question. I thought for a moment how to phrase it without hurting her feelings. What made you decide to become a call girl? I mean, no offense, but aren't they usually anorexic types?"

"You mean thin and beautiful?" she asked, with a trace of pain through a forced smile.

"No, no, not at all, Toni. I mean some of these girls look like they're one meal away from the grave. I don't like skinny chicks in the first place, so it's not like I would want one. I like a girl with meat on her bones! I mean that, too!"

She knew that to be the truth because all of the women I dated were far from thin, and some were a good bit overweight. I liked a girl who was comfortable in her own skin, regardless of how much she has. My only requirements for a woman's proportions are that she's large on creativity and IQ, preferably both.

"Well, like father like son in that department. My ad said that...she trailed off. Maybe it would explain a few things if you saw it for yourself. She winked at me and disappeared again into the den. She came back with a magazine and handed it to me. "Page 22, near the bottom."

It was obviously an escort directory, with a relatively small ad near the bottom. It read:

Sassy Shelly - Specializing in orally satisfying gentlemen of significant proportions. Call (xxx) xxx-xxxx to discuss a pleasurable discrete encounter. $1,000.

I looked at Toni. I re-read the ad. I looked at Toni again.

"Yep, Sassy Shelly, at your service!" as she stood, she smiled and lifted her hands above her head and bent her knee like she was modeling a new car.

I started to laugh and then the two of us were laughing. It grew like a snowball. The house was shaking with two drunk people laughing their asses off. I'll never forget it.

"Oh, my god that is so fucking funny!" I managed. "Who else knows this?"

"My best friend from childhood who now lives in London and the three of us. That's it."

"Sassy Shelly, huh? That's fucking hilarious. No wonder you two are like teenagers. You fucked each other on your first date!"

"Perhaps you didn't focus on the verbiage in the ad, Keech. I never intended to do anything other than what was in the ad. I stated what I could do and what I would charge to do it."

"What are you saying, then, that you're some kind of world class fellatrix?"

"Exactly", she said with a crisp, confident tone. "I'm the best. I might be the best in the entire world."

She took another long drink and continued. "Where I grew up and we had holiday parties, all of the adults got wasted every time there was available alcohol. I had two male cousins that were a year or so older than I was. Suffice to say that when I was 18 I discovered that I had a natural talent. I guess in the literal sense the 3 of us discovered it together. Both of them had really big tools, long and thick, and I was able to pleasure them almost effortlessly from the very first time. I still remember giving head to my older cousin and seeing his face as he climaxed for the first time. He was so deep down my throat I didn't even taste his come until he began to pull his dick out of my mouth. My other cousin was watching the whole time, so when he pulled down his pants he started coming almost immediately. Instinctively I rushed over and opened my mouth to catch the semen flying out of his meaty dick. He blasted me with a monster sized load of come. We shared a beautiful moment of lost innocence, the three of us.

This is something I was meant to do. During college I dated a few boys but I generally preferred to pick a nice big dick attached to a mediocre guy. I refined my technique over time, so it became increasingly hard to break up with my boy toys. Men have a soft spot for an excellent cocksucker, so I began to limit my relationships to one night stands with a few bed buddies here and there. By the time I met Arthur it had been over 5 years since I had an actual boyfriend.

When I moved to Vegas I thought I would make a fresh start and actually intended to meet someone. I was open to the idea of a boyfriend once again and I was ready for a relationship. I tried to date but I was older and it was hard. Looking back on it, it's clear to me that I found myself falling back into my old routine of pickups and one night stands after a few months. A couple of my girlfriends and I were having drinks one night and one of them said, "I may as well be a call girl. I fuck two new guys a week and all I get is a buffet dinner!" I thought about it afterwards and she was right. It sounds disgusting, but it was a very logical choice I made. I determined that I could have more time to devote to my personal interests if I was able to pay the bills care of the oldest profession. So I spent $250 on a personal ad and got 9 calls the first night it ran."

"I thought you said Dad was your first?"

"He was. After talking with the other men I decided that I didn't want to meet them. Maybe I was just afraid and it took me a few calls to get up the courage to do it, but I think it was just meant to be. He was witty and charming, of course. It was more like he was trying to convince me to go out with him or something. He was totally different with me on the phone than the others, so I decided to meet him and take it from there."

"He bought me a nice dinner and we had a few drinks afterwards. He suggested his hotel, which was good because I didn't really plan that far ahead. We went up to his..." she stopped. "Keech do you want to hear this? I mean, this is very weird!"

"Yes, yes! It's weird but very exciting. It's turning me on Toni. Just the thought of you sucking off your cousins' dicks is really hot. I had no idea you were that into sucking dick."

"Well now you know. Let's continue this upstairs. I want to show you what we've done with the master bedroom since the last time you were here."

She poured us another round and we headed up to their bedroom. I sat down on the bed and Toni turned on the stereo. She put on an Al Green CD and walked over to the bed and sat down next to me.

"We upgraded the stereo and added a few other things to the room. It's great to have a nice entertainment center in the bedroom. We really love and we spend a lot of time in here of course! Oh, do you want to hear the rest of my story?"

"Lay it on me", I replied. Both of us were totally relaxed as she continued her story.

"We went up to his hotel room and he took out $1,500 and handed it to me. When I told him that it was $1,000 in the ad, he said the rest of it was for me if I could deep throat him. He came over to me and began to kiss my neck. I closed my eyes and kissed him on the lips, very passionately. I dropped to my knees and unfastened his pants and pulled them down. His thick tool was peeking over the top of his boxers. I slowly pulled down his shorts to reveal his dick. It wasn't even fully hard and it was already by far the biggest cock I had ever seen except in porno movies.

"In case you're wondering", he said, "it's eleven and one quarter inches long. I got ripped off three quarters of an inch to give me foot long bragging rights."

"I stared in awe as it hardened and thickened in my hand. I was barely able to wrap my hand around it, that's how big it was. His balls were the size of a grapefruit in a thick-skinned bag of testes. I stared at it like I discovered the Grand Canyon or something because he said, "What do you think, Shelly? Are you up to the challenge?"

I motioned him gently back and took the head and a few inches into my mouth. I worked it into my throat, but it was so thick that I could barely breathe. He told me to relax and just enjoy myself. He was so encouraging, not demanding. After 10 minutes or so he was rock hard and wet from my saliva and I was able to work it into my throat. Eventually I was able to get all but 3 or 4 inches into my mouth with a nice rhythm. He was moaning in excitement and I could tell he was close. After another minute or two he began ejaculating what felt like a gallon of come into my mouth. It spurted down my throat, all over my lips and even a few to into my hair, my eyes, it was everywhere! It was amazing."

"I climbed up on the bed and we both just relaxed for a few minutes. He reached over for my hand and squeezed it gently as we stared at the ceiling."

"This is your maiden voyage, isn't it?" he asked. When I asked him why he said that he replied, "You're tender. You're an excellent actress or you're a very nice person. Either way, the pleasure has been mine."

"I'm a bad actress. Do you want to see me again some time? Maybe I can put you on my frequent flyer program."

"I'm in town for the next 3 days and I come back next week for 4 more days. Are you free?"

"I told him I was and we met again for every day he was there. I gave him incredible oral for a week which we both enjoyed tremendously. He gave me over $10,000 to suck his dick for a week, something I would have gladly done for free. We planned to have dinner the night he was going back home on his second trip. It was then that I confirmed his earlier suspicion and he had a good laugh that he was my first and only john. After he got back home he called me and asked me to come visit him. I was reluctant at first given how we had met, but I agreed and began flying back and forth. You probably remember that, when I first came on the scene. And the rest is history."

"That's a fucking bizarre story."

"You think that's bizarre, just wait. I have to discuss something with you. I am going to just go ahead and say it. Since Arthur and I have been together I have either sucked his dick or eaten his come every single day. When he goes on business trips he freezes a few loads for me to enjoy while he is away. I thaw them out and slather up a dildo or just drink it out of a shot glass. Well, this unexpected business trip extension has left me high and dry. He froze 10 extra shots of come but I got really horny two days ago and drank it all. I figured he'd be back the next day and it would really turn him on to know I had eaten all that come."

My cock was rock hard in my pants and was painfully restrained by my jeans. She had begun this latest story by looking me in the eye and was not trained on my groin. It was obvious what was coming next.

"I think you know what I'm going to ask you, so what's it gonna be?"

I stood up as she sat on the edge of the bed, the soft music playing in the background. The lights were dim and I was totally buzzed. "You want this cock in your mouth, don't you?"

"Oh, yes I do! I want to suck your dick Keech. I want to see it, suck it, taste it, and watch you blow a big load of come into my mouth. Show me that tool."

I began to undo my pants and Toni, my 46 year old stepmother, licked her lips like a hungry cat, ready to feast on my fresh meaty member. As I lowered my pants she spun off the bed and eased me to the edge of the bed. She peeled my boxers off and my dick sprung into her face.

"Yes", she hissed. "Yes, this is good. Oh, am I going to enjoy this. There is sooooo much we could do with this one! There are so many places you could explore! We are going to have a good time with this one, oh, yes."

She opened her mouth and in one huge gulp her lips rested on my pubic bone, her lower lip pushed tightly against my hairy sac. She groaned as she jerked her head on me deeper and deeper as the tip of my penis popped into and out of the tight opening at the back of her throat. I probably measure somewhere around 6 or 7 inches and I've met a few women that could put it away, but Toni made all of them look like amateurs by comparison. I could tell when I was inside her mouth for the first few seconds that this was going to be an experience like no other.

She opened her mouth wide and forced me even deeper into her warm wet mouth. Her eyes were closed as she strained to get every possible millimeter of my hard dick into her mouth, then closed her lips very hard and slowly withdrew. She clamped down and sucked deep again and repeated this a few more times, carefully and deliberately inching my tool in and out. The sensation was amazing and I soon felt orgasm approaching. I wanted to hold out as long as possible in case this was all there would be this wonderful evening.

Toni, apparently sensing the tension in my body, retreated from my cock and as soon as it slipped out of her mouth began to slowly stroke me with her right hand.

"Don't hold back", she said with a smile. "Give me a nice big load as soon as you can. You're going to come more in the next few hours than you have in a week."

She returned her attention to my cock as she began to massage my balls using her fingertips to push the skin in a downward motion, gently stretching the skin of my balls into a sensitive sheet of flesh. "Oh, could I get used to this", she said as she stared at my dick, pursed her lips and ran them in a lengthwise sliding kiss along the length of my shaft.

After only a few more seconds of her "licking the envelope" maneuver I was tightening and twitching and she began a long groan. She began to hum with her lips pressed against my dick, and the vibration felt fantastic. I was only seconds from coming as she hummed louder and slid up to the tip, mouth wide and ready. Again with the proficiency of a pro, she had my entire dick in her mouth, balls to the chin. She was staring at me and juking her head toward my body to force my cock into her throat again and again, growling all the while.

That was it. I felt a deep, dizzying sensation followed by a strange calm. The entire room went quiet for a split second, and then the music came back on. I delivered a healthy load of cream as she sucked, swallowed, and hummed her vibrato happiness tune. After the first load shot deep into her throat she withdrew to taste my come and suck the subsequent blasts into her mouth. She swallowed quickly to keep up with the substantial flow of semen.

She lovingly and gently massaged the last droplets of come into her mouth and onto her fingers, which made their way to her tongue and lips. "Delicious", she said quietly as she crawled up onto the bed. She lay beside me for a few minutes and I reached for her hand.

We lay there for a while and it was Toni that broke the silence. "I have a few more surprises for you Keech if you want them."

I knew exactly what she meant and just looked at her and smiled.