It's All Relative Ch. 04

He stepped to the edge of the bed and leaned forward so he could reach under Dorothy's dress. She jerked at his first touch rubbed her thigh but then relaxed as the palm of his hand slipped over her pussy. Her pubic hair was long and matted with wetness. She gave another slight twitch when he let his index finger slip between her lips. Her lips felt puffy and when the tip of his index finger found her clit she moaned into John's mouth.

Matt let his finger slip up and down her lips a few times. She was wet and ready. He crawled up to kneel between John's outstretched legs. It was awkward to say the least but he got positioned and asked, "ready?"

Again, there wasn't an answer.

Matt slowly lifted Dorothy's dress up to reveal her ass and her ass was pretty damned nice, there were tan lines from her suit, and nary a blemish in sight. Matt looked down to see her pubic hair sticking out a bit from between her legs along with her protruding pussy lips still swollen from John sucking on them.

Matt flipped her dress up onto her lower back. Luckily the front of her dress covered John's junk. He had no desire to see that. He reached down and took his cock by the base, shifting his hips forward just a bit he let the head touch Dorothy.

He expected her to flinch away but instead of a pulling away reflex, Dorothy's ass shifted toward Matt and her hips tilted down toward the bed turning her pussy away from him and more toward John.

He figured that was her comfort zone so he rubbed his cockhead up and down her slit and watched as her lips spread around him. She had a woman's pussy, full fleshy lips smoothly sliding around his head with the inner lips just visible. His cockhead rubbed over her clit

She had a sizable bump there. "A fat one" he thought to himself.

Matt's cock found that soft wet depression which marked her entrance and he positioned himself ready to enter. Dorothy took the initiative and pushed her ass back toward him but further rotated her hips down, away from his cockhead. He placed his hands on her hips and pushed forward.

Her vaginal opening was not quite so easy to penetrate because of the way she'd rotated her hips. He pushed forward as she pushed back and all that was being accomplished was turning his cockhead into a mushroom shape. She shifted her hips down again. Most women rotated their hips up and toward the man when in this position, not Dorothy.

Matt grabbed his cock again and moved it around a tad. That was enough and he saw her lips engulf his cockhead as they slipped around the head. He briefly thought, "there we go" as it felt like he had slipped inside. But her pussy didn't open up allowing him to slide in, he met resistance. In fact his cock stopped again.

Matt looked down at his cock. Her lips were stretched around the head but the bottom of the head was still visible. He thought he was inside but was meeting unexpected resistance.

Dorothy wimpered into John's mouth and pushed back.

"God your're tight," Matt said. He moved up and down a bit, then used his hand to slip up and down her lips again thinking more juices were needed... then something occurred to him.

Matt stopped pushing and asked, "Risking ruining the mood, I have to ask something of you." He paused... "When you said you had used dildos and other marital aides were they for him or her?"

Dorothy stopped kissing John and lay her head on his left shoulder, her ass still sticking up in the air.

John replied, "To be honest we used them on me. We'd heard that anal stimulation could result in an involuntary erection so we tried a few things, but they didn't do anything we'd hoped."

"So Dorothy never used them?"

Dorothy turned her head to the side and spoke for the first time, "No, only John. We thought about it but using one seemed dirty. So we didn't."

Matt pressed his cock against her again, "How many times did you make love before the condition prevented it?"

Dorothy moved her ass a bit but said, "Quite a few times."

"And John was able to attain erection then?" he had to ask.

"Oh yes," she replied and her head bobbed up and down. Matt could hear kissing sounds, she was kissing John again.

Matt looked over Dorothy's back to John. "Um, I know we agreed to no random touching but, well... I need to check something. Would it be ok if I touched you again? With my fingers."

Dorothy said, a bit too quickly, "Yes."

Matt pulled his cock back and slipped his right index finger between her lips again. She was very wet. He slipped down over her clit and then slid up her slit until his finger tip found her vaginal opening. He slid his finger in.

Dorothy tensed up and her pussy tightly contracted around him. His finger only entered about an inch, only to just beyond the first knuckle and she was very tight around him.

He pulled his finger out and considered this for a few moments. Then he said, "Would it be ok if Dorothy feels my erection to compare it to what you used to get? She's really tight..." Matt asked hesitantly then quickly added, "I don't want to hurt her."

"Only if she is ok with it."

Dorothy again didn't say anything but moved her right hand between her legs. Matt felt her finger tips graze his balls and she said, "Yes, it's the same".

"Dorothy, please, put your hand around my penis and really feel it. Humor me if you will."

She lay down on top of John in order to extend her reach. Her hand returned to his cock and she grasped it.

"Oh!" she said.

Her little hand hardly went all around it but it was quickly apparent she was surprised by what she felt. She didn't say anything but her fingers explored the cock and then drifted to his balls cupping them and then returned to his cock squeezing it.

Finally she spoke, "Well, you are harder than I remember John getting."

"I'm harder," he absently repeated what she'd said.

"and maybe a bit bigger." she added.

Matt looked down to her pussy, he moved his cock back so the lips were wrapped around his cock again.

"Excuse me again but did you use kotexes or pads"

Dorothy laughed and he felt her lips tighten at the same time, "Those days are long gone Matt. But I never used the inserted kind, they never fit and it didn't seem right."

"How about porn, have you ever watched porn as a couple? Some people use it to get aroused." Matt was chasing a thread of an idea.

Dorothy quickly answered, "God no, that'd be disgusting."

Matt thought to himself, "Never fit? Shit... If John's condition affected him much earlier than they thought, he may never have been erect enough to fully penetrate her, she never used kotex..." then, "FUCK! I'll bet she's still a virgin."

Matt pursued the idea, "Did you have any experiences before John?"

Dorothy said, "No, I've only ever been with John."

That's when John stepped in, "Matt, what the hell are you trying to say?"

Looking down at Dorothy's up turned ass, "Well, um... I'm not sure how to say this exactly... but Dorothy is tight, I mean really tight. Much tighter than any woman I've been with. Given her lack of well... manly diversity, and your condition," Matt hesitated for a moment fearing the revelation might put them off, but then finally said, "I think it's possible Dorothy is still a virgin."

There was silence.

Then Dorothy started to laugh and was the first to speak, "That's not possible. We made love a lot before the surgery."

"What do you consider, a lot?" Matt asked.

Dorothy kissed John and replied, "A lot, at least 3 times."

Matt thought to himself, "Three times? Three! Hell I've done that in one night."

"Ok, does where I am now feel anything like when John made love to you?" he asked.

She moved her ass a bit, "You're at a different angle because I was always on top, but yes, it feels pretty much the same."

Matt let his cock slip from between her lips and moved his hips against her ass as his cock slipped between her legs and up her slit the head slipping over her clit. "Is that more like the angle?

"Yes" she replied and rotated her hips a bit.

His cock was now no where near entering her pussy but was sliding between her lips and over her clit.

He stroked a few times letting his cock slip to her taint until stroking up her slit again. Each time he'd catch a bit of pussy as his cock slipped across the entrance to her vagina and tried to change paths.

"Good Lord, she's a 52 year old virgin and doesn't know it." Matt thought to himself.

After a few minutes of his cock sliding across her pussy Dorothy's head hung and her breathing was deeper each time he crossed her clit.

John slid up the bed and put his hands on the back of Dorothy's head as she did what she could to his cock. It must have felt just fine because John got lost in it and moaned every so often... but, alas, no erection for the poor guy.

Matt decided to simply continue what they had asked of him. John managed to orgasm and Dorothy swallowed it down just about the time she orgasmed from essentially masterbating against Matt's cock. Although if felt really nice sliding over her pussy Matt didn't cum. His mind was very distracted with the whole thing.

When they were finished they lay on Matt's bed. John stepped into the bathroom leaving Matt and Dorothy alone on the bed.

She was laying back, her head on a pillow as she smoothed her dress out.

"Dorothy can I ask one more question? It's a personal one again."

She smiled prettily, "I suppose so, we've gotten pretty intimate."

"Have you ever used a dildo to masterbate?"

Dorothy laughed again, "You sure are focused on that aren't you."

"I'm sorry, it's on my mind."

"Well the answer is no, I didn't and don't. Anything I need I get from my husband." She paused, "well, almost everything." Dorothy sat across from him straightening her dress, the dress she was naked under. Ever the psuedo-shy woman.

But Matt noticed she kept shooting glances at his cock. He sat up, spread his legs so his cock hung down in it's now semi erect state and asked, "Is there something you'd like to ask me?"

Dorothy shot a look at the bathroom door and whispered, "Does is always get that hard?"

Matt looked down at it and said, "Yes, pretty much, that's it's natural state when aroused. Men's cocks get hard and grow a lot in size. Just how big they get depends on the man." He decided not to address her virginity.

Dorothy sat looking at it until John returned, dressed, from the bathroom.

They both hugged and thanked Matt for his helping them just as if they'd simply dropped by for supper. When they were finally gone and the door closed, Matt slumped into his chair and pondered whether he should have slipped her the long hard one when he'd had the chance. But his good graces had gotten the better of him and he didn't want to ruin their relationship by suddenly ripping Dorothy.

He sat there until 3 am mulling over it.

The next day around noon Matt was sitting in the sun nursing a beer outside the coach when John strolled over.

"Hiya, John, would you like a beer?"

"Thank you kindly but no." he replied as he sat down next to Matt.

"We've got a favor to ask of you again."

Matt was immediately interested and anxious at the same time, "Hell, if it's anything like the last favor I'm all for it. But, go ahead, shoot."

"Well," John began, "When we got back to the house last night Dor and I talked about all your questions and... well, we...um... well, we decided you may be right. You know, about me actually penetrating her. So... um, Dor decided, I mean we mutually decided, to ask you if we could drop by tonight and talk about it."

He paused and then from nervousness, continued. "I'd hate to think that my wife would remain a virgin her entire life because I can't be the man I want to be. She deserves to be a woman. Feel what a woman should feel."

Matt nodded but didn't speak. It was quite the situation he was being drawn into. He really felt for John. He was a good guy and wanted the best for his wife, enough to see her fuck another man, all simply because of his health.

John sat looking out across the lake, "Well, anyway, we'll drop by around 5. We're not looking to eat, just to visit." With that said he slapped his knee and headed back to the office/house.

The coach bell rang at a tad before 5 pm. Dorothy and John stepped in. She was wearing a dress just like the one last night but a different pattern. This one was a purple backless sun dress with yellow flowers. Really pretty.

They sat down and small talk ensued. After three bottles of wine, Matt had to delve into his secret stash of box wine he loved but knew wasn't very elegant.

Dorothy was again drinking more than she normally did. A bit of liquid bravery never hurt. It was probably more than she should have because it only reinforced the nervousness which hung over their conversation.

About 7 pm there was a prolonged pause (the pregnant kind where everyone is avoiding a topic) and Matt saw Dorothy squeeze John's leg again, closed her eyes, and looked down.

John suddenly said, "The reason we stopped by was because what you said last night has been bothering Dorothy, I mean bothering us, a lot. We're here to ask you... if, um... if you would, or would agree to having sex with Dorothy again." another pause... "I don't mean making love with the foreplay which accompanies it. Sex as you know it. But this time I won't participate. And, well, she doesn't want you to wear a condom. She wants to feel you."

Matt's eyebrows shot up, "Oh?"

"We've never had to use one and she didn't like the feel of it."

"Oh, ok."

"I'll be in the room, but, well... the thought of Dorothy being with another man has been on my mind for quite some time. Not just about last night, but, well... for years. Last night was especially, um... rewarding to me and Dorothy enjoyed herself as well."

Gesturing to Dorothy he said, "Dor isn't a loose woman and still doesn't want to strip and jump into bed..." he went on and on and Matt let him.

It was obvious that John needed to get this off his chest but while John spoke Matt kept his eyes looking Dorothy up and down. She just kept drinking wine and looked lovely in the dress. Her legs looked freshly shaved and she had on a perfume he really liked. Then it occurred to Matt. He'd never noticed her wearing perfume before.

"Matt?"

"Huh? Oh right... I'm sorry. I would be honored to be with Dorothy and I'll do what ever she wants and no more. She will be in complete control. If she says 'stop', I'll stop. Is that acceptable Dorothy?"

He finished by asking Dorothy because John's hesitation and repeated references to Dorothy's desire meant she was quite probably the one with all the questions. John seemingly wanted to be an involuntary cuckhold husband.

Dorothy nodded and said, "Yes, yes that's fine," paused for a moment as if pondering something and then nodded as she said, "Yes," yet again.

They retired to the bedroom.

Dorothy and John stood nervously.

Matt decided that he needed to kinda of push them along. Without asking Matt stripped and lay in the center of the bed, he put his arms behind his head and spread his legs. His cock was gaining interest but mostly lay against his right thigh. He reached over to the bed stand and pulled out a small bottle of AstroGlide lubricant and a towel. He lay them aside.

John sat down on a chair and Dorothy remained looking at Matt. There was that long uncomfortable pause, it was clear they had no idea what to do from here.

Matt broke the silence, "Come over here Dorothy" her said and pointed to the left side of the bed. Dorothy walked to the side and stood.

"Closer," when Dorothy took a step closer Matt put his hand on the back of her knee and moved her right next to the edge of the bed.

"You want me to be fully erect tonight, right?"

Dorothy nodded.

"I'll need to be aroused, I dont' ask you to do anything but I'd like to touch you, ok? It'll help me."

Dorothy nodded again.

Matt expected his touching her would do the trick for him. "Don't take your eyes of my penis," he said.

Matt was ignoring John at this point on purpose. He wanted Dorothy to focus on him and forget John was in the room.

Matt let his right hand drift down his belly to his cock and he began to stroke it, Dorothy's eyes watched intently. He let his left hand caress her right calf a few times and then stroked his way up to her knee to linger there. He tapped the inside of her knee and she moved her feet apart for him to let his hand curl around the back of her leg and drift up her inner right thigh.

Matt watched Dorothy's eyes, they stayed glued on his cock as it began to respond to his ministrations. His fingers traced the soft inner thigh and felt warmth and then the wisps of hair. Matt's fingers gently kneaded the flesh on her upper thigh before he let his fingers wander up and touch her pussy.

Dorothy's thighs trembled just a bit and there was a slight intake of breath but her eyes stayed on his growing cock. Matt let his fingers go to work and in very short order she was wet and his cock was standing tall.

John and Dorothy both were looking at Matt's cock Matt knew it wasn't huge but it was certainly a lot bigger than John ever had been.

Suddenly Dorothy reached out to touch his cock. At first she let her fingers run over it as if exploring. Then she would grip it and release... then grip again... until she finally gripped it and began stroking like Matt had been. Matt took the bottle of lube and squirted a bit on his cock. She slicked him and started to jerk up and down quickly.

"Slower," Matt said and gently took her wrist and slowed her down. He showed her how to run her hand up over the top and then down to the base. How to handle his balls, John's balls were much smaller and tighter to his body. Matt's hung low.

Dorothy's breathing was deepening, his fingers were wet with her juices and Matt thought he could see nipples pushing against her dress.

Matt broke Dorothy's trance like stare on his cock, "Dorothy... I'm ready when you are."

Like last night Dorothy didn't remove her dress. She hiked it up a little and crawled onto the bed and on top of Matt. Her back was to John. She settled onto his cock and began to slip it between her pussy lips... up and down.

"Is this how you made love to John," Matt asked.

Dorothy's eyes were closed, but she nodded and said, "Ya, this feels really nice."

Matt put his hands on her hips and stopped her movement.

"Raise up," he said as he lifted her by the hips. She hovered over him.

"Stay there" he said as he let his right hand slip under her dress and he grabbed his cock. He pointed it up, "up just a bit more" he asked.

He watched Dorothy's reaction as she felt the head of his cock slip between her lips back and forth over her clit a few times and then stop at the entrance of her vagina. Which she seemed completely unaware of.

"That's the wrong angle" she said, "you're just poking me."

"Trust me," he said as he held his cock in place. "Now slowly let yourself down. Don't worry about where my penis is."

She lowered down and the head of his cock slipped between her lips only to run in to the resistance again.

"There feel that?" he asked.

"Yes," she said softly.

"That's what we have to get past, just keep lowering yourself."

Dorothy lowered and the pressure grew on the head of his cock. Her face reflected a slight grimace and he sensed her stopping. With his cock firmly held in place he released it and put his hand back on her hips.

She started to lift up, "No, no, don't stop now." he said.

Dorothy turned her head to the side and said, "But it's starting to hurt, sex isn't supposed to hurt."

Matt held her in place and said, "What you're feeling is your hymen stretching. Sometimes they stretch and sometimes they rip a little bit. It's normal for a woman to feel a little pain the first time. I'll be as gentle as I can me. "