by Holly Ardent
“I probably wouldn't have opened the door for you,” Jessica said.
She paused for a moment's thought.
“I remember thinking that you looked clean and presentable, just like a delivery person ought to.”
“So, you made the same call you're complaining about. You judged me by my appearance. Clothing is part of that, a large part of it. If I'd been wearing dirty clothes I'd still have been the same person inside.”
“Did I mention that I hate logic,” Jessica said. “At least when it's used against me.”
“Sorry, it sounded like you were actually wondering. I apologize if I offended you.”
“I'm not really offended, just kicking myself. Someone told me something similar a long time ago, but they didn't explain it that well. They just told me to ignore it because guys were very visually oriented.”
“They are, I'll admit that. But so are women, at least lots of them. As you said, I looked clean and presentable. So, there's a visual stimulus reference from a woman.”
“Please don't use my own words against me,” Jessica said.
“Alright, but did I manage to explain it well enough for you?”
She sighed.
“Yes, you did. I understand the point. I just think it's unfair.”
“It may be, but it's unfair for everyone. So that at least levels the playing ground and puts them all on equal footing.”
“I'm not sure I agree with you, but I don't want to argue, so I think that's enough of that topic,” Jessica said. “Can we talk about something else?”
“Sure, you were talking about your job, what do you do? You know what I do.”
“Well, my job title is clerk, but what I really am is a glorified librarian at a law office. I run the records room, so lawyers ask me for files. I find them, deliver them, and then make sure they're returned to the proper place after they're done with them.”
“Well, that beats driving groceries around.”
“I'd have to disagree, at least if the driving around includes the things Cheryl was telling me about.”
“There is that,” Jack said. “Although I didn't plan it that way, it just kind of happened.”
“Cheryl's like that,” Jessica said with a smirk. “She gets her way far more often than not.”
“I understand and I'm not complaining at all. It's just still a little bit of a shock when I think about it.”
Jessica laughed.
“I'd imagine it must be. Poor little Jack, dragged into the embrace of an older woman. Wait, make that several older women.”
“Oh no, not a shock like that. It's just a shock that all these women are physically interested in me. All the younger girls I've dated kept pushing me away, not wanting to do anything unless they were in a 'serious relationship' with me. Now I've got one woman that keeps recommending me to others and they all don't care that there are others.”
“I wouldn't know about that. I've only had one man as a lover, my husband. He completely disappeared a year ago though. No sign of him anywhere and he hasn't touched our credit card or bank account. Just here one day, gone the next.”
“I'm sorry,” Jack said. “I didn't know.”
“I'm not sure if I'm sorry or not. I don't know that he ever really loved me. At least he married me when he got me pregnant right after high school. I thought I loved him, but when he disappeared it was as much of a relief as it was anything else.”
“It sounds like things weren't that great for you,” Jack said.
“They were okay, there just wasn't anything great, it was just … acceptable. It was a very hum-drum, mediocre life.”
Jack decided to try to guide her towards what she'd agreed to with Cheryl.
“Cheryl said you had a much different attitude about sex than she did,” Jack said. “That you didn't much like it. Was that mediocre also?”
“How would I know? He's the only one I ever had. He tried all sorts of stuff with me at first, but it never really did anything for me. So by the time he left, there wasn't any variety. I just gave him what he wanted and was happy when he was done.”
“Ouch, I'm sorry.”
“Why?”
“Because it sounds like you've been missing out on some things,” Jack said.
“Well, that's why I agreed to Cheryl's offer. I'd like to enjoy sex, it's supposed to relieve tension and, trust me, as the only adult in this household there's plenty of that. Even if it didn't do anything else for me, sometimes I felt less tense after. But I think Cheryl was exaggerating again when I talked to her. I'm willing to give it a shot though.”
Jack stood and walked over to her chair. He looked at her face as he lowered his hand to her leg, trying to be sure that it was a welcome gesture. Jessica relaxed when she was what was happening.
I'm glad I decided to initiate things, he thought. I bet she never would've and we'd have been sitting around talking until her kids got home.
He sat on the corner of the couch next to her and gently massaged her leg through the fabric of her skirt.
“What would you like to try then?” he asked.
“That's the problem, I don't know. Like I said, the only man I've had is my husband so how would I know?”
She raised her hand to her mouth and chewed on her knuckle for a moment.
“Would you do everything to me that you did to Cheryl?” she asked softly.
“I'd be happy to, but if you change your mind while we're doing something, just tell me. Did you want to try the things she did to me too?”
“I can't be like her. I can't be that forward with a man. I'm sure you noticed that you had to take the first step here.”
“No, not like that. I meant the physical things she did to me,” Jack said.
Jessica blushed.
“If you tell me what she did, I'll try.”
“I think that what we ought to start with is me doing something to you, that Cheryl did for me,” Jack said.
She looked at him inquisitively.
“Are you going to have me making the calls as to what we do?” he asked.
“Would you, please?”
“Then I want you take off the sweater, skirt, shoes, and nylons. Then lie face down on your couch.”
Jessica looked nervous.
“Here?”
“Why not? The curtains are closed, I'll slide the chain lock back on while you get undressed. You said you wanted me to make the calls, so I'm making them.”
She was slightly hesitant but her hands went to the bottom of her sweater.
“Can we shut the lights off at least?” she asked.
“Oh no, I want to see every last inch of you. I'll enjoy seeing every last inch of you.”
Jessica's blush intensified.
“If you insist,” she said.
“I do.”
Jack got up and refastened the chain lock on her door.
* * *
Jack turned from the door to see Jessica rolling down her stockings. Her sweater was sitting on the couch and he saw the back and sides of the black, lacy bra she was wearing. Her shoes were on the floor next to her. When she finished removing the stockings, she stood to shimmy her way out of the pencil skirt. In the process she revealed underwear that matched her bra. He watched her ass greedily as she swayed her way out of the skirt and laid down on the couch as he'd indicated.
Jack walked back to her and sat on the edge of the couch next to her legs. He reached up and took her shoulders in his hands. Then he began to massage her.
It was obvious she'd been telling the truth about wanting some tension relief. Her shoulders were like rock under his fingers. He dug into the task.
She flinched several times, but he didn't offer to stop. Once the original tension was relieved, he continued with a softer massage. The flinches were replaced by groans and sighs of relief. When he judged that her shoulders were as relaxed as he could get them for now, he moved down.
Jessica's bra strap was in the way so he unsnapped it and
pushed either side off her back. She tensed up when he did that, he saw her shoulders rise. A sharp tap from his index finger on either shoulder got her lying flat again and he continued with the massage. He was very careful to make sure to include the sides of her torso, and the sides of her breasts. She started to flinch again when he made contact there, but when he immediately withdrew his hands, she calmed. He had to repeat the process three times before she stayed still when his hands made contact with the flesh of her breasts.
He continued massaging down her body. He thought about removing her panties, but decided that it would probably be too much for her yet. He spent a long time with his fingers grasping and rubbing her ass. She'd barely flinched when he first got to it and when the massage slowly turned to caresses, she didn't flinch at all.
With regret, he pulled himself away from her ass and worked lower. Her legs were long, and smooth to the touch. He felt the knots in the muscles when he began working on them, but they were soft and pliable under his fingers when he was done.
When he began to massage the soles of her feet she uttered a sound of exquisite pleasure. He finished with her feet and moved back up, caressing her ass again.
“That's wonderful,” she said. “But what does it have to do with sex?”
“Well, now you're more relaxed and, more importantly, you're used to my touch.”
Jack ran the tip of his finger along the side of her breast to demonstrate his point. Jessica shivered with pleasure.
“I'm not complaining, but what does touch have to do with sex?” she asked.
Jack brushed his hand down her side firmly, Jessica shivered.
“Touch is very good to heighten the mood and to build anticipation.”
He bent over and placed his lips on the nape of her neck. He slid them up until they were pressed against the skin just below where her hair started growing. He slid his tongue out between his lips and slowly kissed and licked his way down to her back.
Jack leaned up. He took her arm and gently rolled her over. Her breasts splayed gently to the sides as she settled on her back. He reached out and started to slide her panties down.
Jessica gave a long sigh.
“What?” Jack asked.
“I had high hopes that you weren't just going to strip me and take me. I want to find out what all the fuss Cheryl and the others were making is about.”
Jack chuckled.
“I'm not going to fuck you anytime soon. I do want to see all of you and have ready access to your body though.”
She gulped.
“Oh, um … alright?”
Jack finished pulling her panties off and tossed them with the rest of her clothing. He stared at her for a moment, drinking in the sight of her long body, her olive-toned skin, and her lustrous dark hair.
“So many choices,” he murmured.
He settled on reaching out for her breasts. He took one in each hand and stroked them, almost to the point of continuing the massage. After a few moments of stroking her soft skin, he turned his attention to her nipples.
A good firm pinch got a sharp intake of breath from Jessica, and a large increase of size from her nipples. He tugged and pinched gently, wanting them fully hardened. Once he was convinced they were there, he leaned over and slid one between his lips. His tongue gently caressed it as he tasted her.
Clean, something a little spicy, but there's a touch of something sour. Is she scared? That might do it.
He switched nipples, stealing a glimpse at her face as he switched. Her eyes were closed. But she was gnawing on her lower lip.
He worked her second nipple over as he had her first. When he was done, he looked up at her face again.
“Why are you chewing on your lip?” he asked. “It looks like you're trying to hurt yourself.”
“Because of what you were doing. The last person who did that was my youngest child,” she said, then hurriedly corrected herself.
“Well, not exactly that, but you know what I mean.”
“What? You've got great nipples for sucking on, why ...”
“Oh, well, Eddie thought the idea of using his mouth on me, anywhere but my lips, was gross. Of course, me using my mouth on him was just fine,” she said bitterly.
“I begin to understand why your opinion of sex is what it is,” Jack said.
He lowered his mouth to her breasts again, but this time he licked his way down first one, then the other. His tongue left a light trail of moisture as he made his way down off of her ribs and onto her stomach. He paused for a moment at her belly button, dipping his tongue into it a few times, just because.
Jessica's giggle surprised him.
“That tickles,” she said.
He pulled his tongue out of her navel.
“Sorry, didn't mean to tickle you.”
His tongue ducked back down and traveled from just below her navel to the top of her thick patch of pubic hair.
I'll be picking hairs out of my teeth all night, he thought. But, then again, that's a small price to pay for having a lady who's this hot.
Jack got up on the bottom of the couch and turned his attention back to Jessica. He pushed her pubic hair to either side with his hands, then slipped his tongue into her.
She's good to go alright, but not yet. I want her to cum hard before I fuck her. Give her two or three orgasms, then see if she can say that sex isn't all that great with a straight face.
As Jack drove his tongue inside of her, his fingers wandered around the edge of her pussy, stroking and exploring. Jessica was very sensitive at the top of her cleft, just below her clit. He found himself eager to see if that sensitivity extended upwards just a little.
He let one hand wander upwards and put pressure on her clit through the hood of flesh that covered it. Jessica immediately started squirming and moaning. He took his hand back off and licked his way up her pussy to her clit. His fingers slid the hood off of it and he bent down to take it in his mouth.
Jack was gentle, to start. He used his lips to pinch her clit lightly and his tongue to lash it gently. Jessica reacted as though he were mauling it, thrashing and writhing enough that he had to hold her down with his hands. The hood covered her clit again when he let go, but Jack continue to play with it through the covering of flesh and Jessica continued to react.
When she stopped writhing and tensed up, Jack stepped up his oral attentions.
I'm pretty sure she's having an orgasm, let's see how long I can make it last.
He kept her tense and rigid for about three minutes before she started to go limp. He stopped sucking on her clit and sat on the floor in front of the couch, watching her face.
His hand reached out and stroked her taut stomach. He had no idea how old her youngest was, but she'd certainly gotten fit again since then. His idle fingers moved upwards, stroking the underside of her breasts. They feasted on the softness of her flesh until they encountered her still hard nipples. Then they stopped to play. Jack didn't even think about it, his fingers just started pinching and pulling.
He was watching her face and, for a moment, didn't realize why she was tensing up. Then he realized what his fingers were doing and he placed the little twitches and twinges in her face as her reaction to his fingers' actions.
He pulled his hand away quickly and chastised himself.
Wait, let her recover. It'll be all the better for her next time if there's a break in between.
Jack sat patiently for several minutes before Jessica stirred.
“What the hell was that?” she asked.
“What was what?”
“What did you do to me? That was ... I don't know, I don't have the words.”
“You haven't ever orgasmed before?” Jack asked.
“I thought I'd cum before. It didn't seem like anything too special, but this was way beyond that.”
Jack grinned.
“Good, that's a good start.”
“A start? That's just a start?” Jessica asked.
“Jes
sica, I haven't even taken off any of my clothes yet.”
“Let's fix that. Better yet, let me fix that for you. Can I? Please? And call me Jessie, not Jessica. I think that qualified as a proper introduction.”
Jack stood up and gestured to his belt. Jessie sat up on the couch and reached for it. She took her time undressing him, stroking his body as she did. When she slid his underwear down, she bit her lower lip again.
“What's wrong?” he asked.
“That's, ummm ... Let's just say Eddie wasn't nearly as well equipped as you are.”
“That's not going to be a problem, is it?” Jack asked.
“Hell no, I just don't think I'll be able to get all of you in my mouth.”
“Only one way to find out,” Jack said.
She nodded eagerly and leaned forward. Her lips wrapped around the head of his dick as she started pushing her mouth onto him. She got him more than half way in before having any difficulty. A little past half way she gagged.
Jessie backed off, sliding his dick out of her mouth a little, and then tried again with the same results. Jack was sure she was going to hurt herself after the third attempt so he reached down and demonstrated the standard cheat by taking her hand and placing it on the base of his cock, just below her lips.
She kept her hand still and started bobbing her mouth up and down his dick. After a minute of that, Jack reached down and closed her hand into a fist around himself and moved her hand up and down a couple of times. Jessie got the hint and started using her hand on his cock in rhythm with her mouth.
Jack reached out and grabbed a handful of her hair. Then he drew his hand in against the back of her head. He used that hand to slow her bobbing, drawing out his pleasure. Jessie made no attempt to resist his control of her head, if anything she seemed to relax a little bit more.
After a few minutes of that, Jack wanted more. Her mouth was nice, but he wanted the warm, wet cunt he'd been playing with earlier. He wanted to watch her orgasm beneath him and not stop whatever had caused it, forcing her to cum until she couldn't any more. He pulled her head back.