Unsophisticated but Tricky

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Who thought that sleeping pills lead to sexual nirvana?
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I'm not real good with words, so if you need a vocabulary test this isn't the story for you. What I'm best at are things that require brawn and an active cock. As the title states, I'm unsophisticated but tricky; and many of you will probably consider me immoral too; but that's your problem, not mine.

I'm also not one for flowery background stories so I'm just going to lay out the basics, with fake names.

I'm Blake. I married Cheryl when we were both nineteen, after High School, the furthest either of us went in school. Cheryl is better looking than me, and has a nice body, but I also have a nice body, especially my dick and biceps.

Cheryl is the by far the best looking member of her family; in fact I am quite certain that a DNA test would show that her biological father is different than that of her two sisters. Her mother and two younger sisters have bodies as nice as Cheryl's but their faces are just short of someone fucking them wanting to use a paper bag and a crayon.

Cheryl's father died in an industrial accident two years before Cheryl and I got hitched. In my meetings with him he seemed to be a nice guy, and he also seemed to be smarter than the other family members. He had really good life insurance - much better than anyone else that I had heard of in our town - and also Cheryl's Mom, Bernice, got a big city attorney to sue the company responsible for his accident. As a result to say that Bernice has no monetary issues would be an understatement, especially since she has an older brother who is an accountant and who has wisely invested her money - after she splurged on a four bedroom really nice house.

The only drawback to Bernice's wealth is that she has guys who want to hook up with her for the money. That's where I come in. I'm able to discourage any dudes with ulterior motives because of my aforesaid (is that a real word? I like it, but excuse me if I just made it up) brawn. Bernice does appear to be a little sexually frustrated, but for the sake of her daughters she wouldn't do anything stupid to jeopardize her wealth.

After Cheryl and I had been married three years I got a chance to work the night shift for time-and-one-half. We talked about it, and decided that I should do it. It meant that Cheryl, who works nine to five as a hair dresser (I know that she has a three-dollar word for it - cosmonaut, or something like that - but I just say "hair dresser") and I only had time to eat dinner and have a nice fuck every weekday, but since we didn't want to sponge off of Bernice we felt it important that we get the extra money.

Things were OK, except for the fact that my cicada (is that the right word?) rhythms were off and I had to take a sleeping pill when I got back from work at a little before 9 a. m. just as Cheryl was leaving for work. That turned out to be problematic when we had a fire at our rented house, and but for the quick actions of a neighbor kid and his father (who was almost as brawny as I am) I would have been burned to death because nothing wakes me up once I've taken a sleeping pill. Also - embarrassing at the time, but not enough to make me change my M. O. - I sleep nude so until my almost comatose body was covered by a blanket onlookers got a real good view of my cock.

Since the house we had been renting was a total loss, and the only things saved were some keep sakes, jewelry, and important papers that we were smart enough to have in a fire-proof box, Cheryl and I were homeless. Our renter's insurance would help us ultimately recover, but we were strapped for cash, clothes, and lodgings at the time.

Bernice came to our rescue. She convinced us that we should move in with her and her youngest (eighteen years old) daughter Jen until everything worked out. Since there were some issues about how the fire started, and other complications, it could be as long as a year before everything was sorted out, so Cheryl and I decided that we would take advantage of her Mom's generosity and hospitality.

I guess I should have mentioned this before; while Cheryl is a great fuck, she don't like sucking cock. She considers it demeaning. I used to really like blow jobs when I was playing the field, but overall being with Cheryl is better than getting blow jobs, so I don't agonize about it - at least not too much.

Actually, after a week or so of adjustment, living with Bernice and Jen turned out to be nice. I had someone to talk to before I took my sleeping pill, and Bernice assured me that she had gotten something from the doctor to wake me up out of the complete stupor that the sleeping pill put me into should there be another emergency so that I wouldn't die - like I almost had in the fire.

Also, the bed and room that I slept in must really have suited me because most days when I woke up I felt much better than in the rental house, especially my cock and balls. I laughingly wondered to myself if I jacked off in the middle of the night, though there was no sperm on the bedsheet.

Then came the Monday that I worked on a special project at the factory that paid hazardous pay, but that was really hard work. I was so beat when I got home that after a quick kiss with Cheryl, a quick "Hi" to Bernice and Jen, and a quick shower, I hit the sack. I didn't take my sleeping pill probably because the fatigue made me forget.

That day - probably around noon - I was having a great dream. I was dreaming that a babe at a swimming pool was giving me a blow job. It was so real that I actually opened my eyes.

Imagine my surprise when I saw a topless Bernice vigorously sucking my cock while playing with my balls, and once in a while moving her bare nipples into contact with my cock or balls. I decided to see where this went, and closed one eye - the one nearest Bernice who was on the left side of the bed and paying attention only to what she was doing, not my face - and opened the other just enough to see.

Bernice's mouth really - I mean really - felt good on my cock. It may have been the best blow job I'd ever gotten. I was convinced of that when I ejaculated an all-time load into her mouth. I closed my eyes completely when doing that, but couldn't help myself from bucking upward, even though I thought that it might put Bernice on to the fact that I was awake. Fortunately, it had no effect - she seemed to be on a blind mission to get every ounce of cum out of me.

After I deposited my load in Bernice's mouth - I was certain that she swallowed - she lovingly stroked my cock and balls for a while longer, and then washed them off with a washcloth. She gave my cock head a kiss before covering me up with the sheet she had obviously removed to access my dick, and then pulled her top back on, and left the room.

Lots of things ran through my mind in the next hour as I lay awake. First was "that was a real Grade A blowjob, and I felt really, really good - maybe I get them often and that's why I've felt so nice sleeping at Bernice's house." Second, "Bernice has a nice set of tits; although her face is homely, her tits are also Grade A." Third, "how do I get blowjobs when awake so that I enjoy them more."

Like I said at the start, though I'm unsophisticated I'm tricky, so I figured out number three before I fell into a very restful sleep, I'm sure with a smile on my face.

************

The next day I bought one of those hidden cameras - it cost an arm and a leg, but with the hazardous duty pay and not having to pay Bernice rent I could afford it - and installed it with a motion activator so that it had a good view of my bed. I hoped that it would catch Bernice, and also give me a charge to watch myself fucking Cheryl if I chose to turn it on during our fuck before I left for work. I decided to take a sleeping pill and just see what happened.

Imagine my surprise when on Tuesday I saw Jen do essentially what Bernice had done on Monday only with her top on, and on Wednesday saw Bernice service me again. I bucked up just like I did when awake, explaining why it hadn't bothered Bernice on Monday.

When I got home from work on Thursday after Jen left for High School and Cheryl for work, and I took my shower, I had a pleasant talk with Bernice. Then I did my best tricky work ever.

"You know, Bernice, I think that I'm going to have to go off those sleeping pills. The doctor says if you're on them too long you can become addicted."

"Well how will you sleep, then?" Bernice responded, obviously not wanted to give up her blowjobs.

"I've got that figured out. If I can just relax some before going to bed I'm sure that I can sleep. You know what would really relax me?"

"Uh...no...what?" Bernice stammered.

"A nice blowjob," I grinned.

"Uh...but Cheryl...leaves for work...uh...when you get home," she stammered, turning red.

"Yeah, well Cheryl don't give blowjobs anyway. I was hoping that you could help me out?" I smiled.

While Bernice was sputtering and turning even redder, I led her into the living room where I had a DVD from my camera in the blue ray player. Bernice tried to leave, but I held her fast. After about two minutes of the DVD showing Wednesday's activities she was crying and said "Please turn it off."

I sat her down on the couch. "You must really think that I'm a horrible person," she sobbed; "but I get so horny, and you have such a great cock, and I've always liked you - so I thought that there was no harm;" and then she really dissolved into tears.

I hugged her tight. "I don't think you're horrible, Bernice; and I've always liked you. You're kind, generous, pleasant - and now I know that you give the best blowjob in history."

She stopped crying and looked up at me when I said that. "But...but...you're asleep," she moaned.

"I wasn't Monday, which is why I installed the camera that caught Wednesday's action," I smiled. I didn't tell her that it caught Tuesday's too. "I think we can work out what those high-falluting talking heads on T V call a win-win situation. You can relieve your sexual frustrations, and I can get off the sleeping pills before getting addicted. What do you say?"

"But...but...what about Cheryl?" she stammered.

"Cheryl doesn't suck cock even though she knows that I love it and that it would make me happy, and she wants both of us to be happy, and she wants me to not get addicted to sleeping pills; so we're just secretly helping her out," I smiled.

"I...I...don't know," Bernice said. But it was too late.

I picked her up, carried her to my bedroom, gently but firmly removed her top, removed my clothes, and then lay down on the bed with my cock rock hard and sticking up.

After apprehensively viewing me for a minute or so, she licked her lips, straddled my legs, and got to work. As she sucked I fondled her tits - nice B+ cups with good rigidity for a forty five year old, and really nice nipples.

Apparently the tit fondling really inspired her because she gave an even better blowjob than on Monday or - it appeared - Wednesday, and she massaged my balls for the longest time afterward.

When she was done, I grabbed her, pulled her next to me, and with a hand on one of her bare tits I quickly fell asleep.

Based upon Thursday, Friday, and Monday, there was no need for me to ever use a sleeping pill again as long as Bernice was giving me blowjobs and we could cuddle with one of my hands on her bare tit until I fell asleep.

After the blowjob Monday - which was the best ever - before I fell asleep Bernice got tears in her eyes and said "There's something that I have to tell you before tomorrow."

I knew what it was, but played dumb. "OK?" I said.

"Jen has an early day on Tuesday, and she caught me blowing you one day and - well as you know she's a shy girl and not that good looking so she doesn't have any boyfriend, and she really likes you and the look of your cock - well - sigh - she told me that she'd tell Cheryl unless she got to suck your cock on Tuesday when she gets home from school around noon.," Bernice said with a tear in an eye.

"You wake me up Tuesday - after you do your thing to put me to sleep - just before Jen gets home, and I'll take care of the rest," I smiled.

I was looking forward to what I expected to be a "double-header" (ha, ha - I'm so fucking funny) on Tuesday.

**********

Bernice did her normal good job of getting me to sleep Tuesday, and about 11:40 she woke me up. "Jen should be here in about twenty minutes," she said.

"Why don't you go out and run an errand," I smiled.

I pretended to be asleep when Jen came into my room about 12;10. Once she moved the sheet off of me and started sucking I grabbed her.

She screamed.

When she didn't see an angry look on my face she stammered "I...I...don't know...what came over me...uh...I've never done this before."

"Let's go into the living room," I said, picking her up and carrying her. When we got there - my cock was rock hard and needed attention - I played a couple of minutes of last Tuesday's blowjob from her. She cringed and started crying.

I held her, said "No need to cry, Jen. I know that you're frustrated, and that you're trying to be a good girl. I don't need sleeping pills any more, but I do need a good blowjob to get to sleep - so I'd really like you to continue."

I smiled down at her and wiped away her tears. After a few seconds she smiled back and said "Really?"

"Really," I responded.

"I...I...have to let you know, though that Mom does..." she started to say before I interrupted her.

"I know - don't worry about that. Let's go back to my room," I smiled.

Jen straddled me, put her all into it, and even though she didn't have Bernice's skill, she did a good job. I told her so as I cuddled her then quickly fell asleep.

I lived an ideal life for the next few months, especially after two modifications. The first was that I talked Bernice into being completely naked and I sometimes fingered her honeypot while she was sucking me, often causing us both to have orgasms. The second was that I talked Jen into going topless. I began to wonder if she had a different daddy than both her sisters too since her tits - which she usually pretty successfully hid - were D+s although her mother, Cheryl, and sister Kate, all had B+s. I learned to really like fondling those puppies once a week, and Jen had orgasms from tit play alone.

When you combine the above with fucking Cheryl - who is a great fuck - almost every weekday before I left for work, and three times during the weekend, I was one happy camper.

Three things then happened that had the potential to spoil my ideal life. The first was that all of the insurance proceeds finally came in, and Cheryl was anxious to get a place of our own again. The second was that Bernice was wanting to fuck because my work on her tits and pussy with my hands was ramping up her libido. The third was that Cheryl wanted me to go off the night shift.

I solved the first problem by getting Cheryl to agree to take a loan of $25,000 from Bernice so that we could put a down payment on a small house of our own only one block from Bernice's.

I was able to stall the third so that for two months in our new house Bernice and Jen would make their usual visits to help me get to sleep.

For the second, after much thought, one day I gave up a blowjob from Bernice to talk to her about it.

"Bernice - as much as I like you, and I love what you do for me, I'm not going to fuck you. That's a line I'm not willing to cross. That is I'm not going to fuck you unless it's with Cheryl's permission," I told her in a no-nonsense voice.

"But how do we get that?" she moaned.

"Listen to my plan..." I said.

After revealing my plan to her Bernice lit up like a Christmas tree. She quickly got naked and gave me a blowjob so intense that it seemed like I came for a half hour straight, and it wiped me out so much I had to beg off fucking Cheryl that evening before I left for work.

***********

I'm not one much for detail and long-winded explaining, so I'll just give you the short version of the plan. I got two guys to act like cads trying to get Bernice's money that I saved her from, and two more guys that really were trying that which I also saved her from. Only one ended up in the hospital - I exercised real restraint.

While Bernice was seemingly almost getting conned out of her money, she was complaining to Cheryl about how she was going crazy without sex, and I was separately constantly reminding Cheryl about how great her Mom was in helping us out after the fire, by loaning us the down payment, and in everything else that she did.

Cheryl unknowingly really helped us out when about three weeks before Bernice's birthday when they were alone Cheryl said to her "Mom, you've been so great the last year, and I'm so worried about your mental state at the same time, what can Blake and I get you for your birthday that will make you happy?"

As Bernice told me later, she seized on this opportunity like a pit bull onto a steak. "Honey...I know that you mean well...but the thing that I want you'll never give me." Then she started fake crying.

"No, don't say that. I'd do anything for you," Cheryl said, holding her hands.

"Not this, honey - it's too much to ask," Bernice fake sobbed.

Apparently after another five minutes of this and Cheryl's even more intense pleas, Bernice straightened up, removed the fake tears from her eyes, and said "You have to promise that whether or not you give me what I want that you'll never, ever, hold this against me, and it won't affect our relationship."

"I promise, promise, promise," Cheryl said, kissing her on the cheek.

"OK, then," Bernice sighed, then blurted out - "I want you to convince Blake to spend the night of my birthday with me."

At first Cheryl apparently looked confused. "You mean take you out to eat, or go dancing."

"No, honey - I mean spend the night in my bed and whatever happens, happens," and then Bernice broke down in fake tears with her hands over her face.

After a few minutes, Cheryl pulled Bernice's hands from her face. "Are you serious?" she asked, although in a non-harsh way.

"Cheryl, honey, I'm just so horny, and all the guys I meet are after my money and assholes besides, and Blake is such a good man and I know that he more than sexually satisfies you, and I'm sure that it would snap me out of the depression I'm in...I'm really sorry for asking. Forget that I asked; I'll get out of my depression somehow," she continued, and then fake broke down again.

After another long pause Cheryl asked "What if Blake won't agree?"

"Then it won't happen," Bernice said. "However, he is a man, hasn't had any other pussy since you've been married, he likes me, and even though I'm ugly I have a really good body for a forty five year old - so...uh...so...well... - maybe he'll do it; if he won't so be it."

After another pause, Cheryl said "Let me think about it."

************

It was hysterical watching Cheryl, the next two weeks, try to convince me to do something that I already wanted to do, but didn't want her to know. She approached the issue at an angle at first, saying stuff like "Isn't Mom the sweetest...she's a saint the way she's helped us...I'm concerned about her mental health from her lack of intimacy with a man...doesn't she have a good body for someone forty five, in fact it looks like a twenty five years old," etc., etc., etc.

I played along, agreeing with all of the nice things she said about Bernice, and expressing my own view that "Maybe what Bernice needs is a good fuck to snap her out of her doldrums. Got anyone in mind - not those con mean and slime balls she's associated with before - but some good decent guy that we could get to help her out. I mean it's not like we'd be asking him to do something that he wouldn't enjoy."

That last comment provided the perfect Segway (is that what you call it, or is that a scooter - sorry, I don't know and spell check ain't helping me) for Cheryl to sit on my lap and stroke my face and ego.

12