Older woman brings a smile to her face
It had been one let-down after another for Jessie. She was in college and dying do an internship before she graduated, but it didn’t look like it was ever going to happen.
Most companies were being too picky. She’d been on a lot of interviews and none had called her back, which she found insulting considering it was free labor.
She’d spent a lot of nights crying, but not just because of that. Her whole life was going straight to shit.
She’d recently broken up with her boyfriend because she’d gone on a trip to Las Vegas without him. He’d been accusing her of cheating since the day she got back because she didn’t call him while she was there.
She explained that she was planning to, but every time she had time to call, something would come up and she couldn’t do it. He didn’t believe her and they’d argued about it so much that it eventually led to their breaking up.
On top of that, her closest friend was moving to Australia. She and this guy were as close as two people could be. It was like losing one of her sisters (he was gay). She was having a hard time getting used to the thought of him not being around.
It seemed like every possible problem that one person could have was coming at her all at once. She spent a lot of time watching comedies to try and keep her spirits up. She didn’t want to look too sad on her interview.
The day of the interview arrived. Jessie felt like shit, but she went anyway and tried to keep a fake smile throughout their conversation.
It had been going well despite the intense nervousness she felt inside. It was like all the mistakes that she had made on her previous interviews were helping her now. She could speak more fluently and answer without hesitation because she’d heard all the questions a dozen times before.
Nina was the woman doing the interview. She was the sexiest older lady that Jessie had ever seen. Nina was blonde, had a distinguished face, and was confident. She wore a sexy form-fitting outfit that hugged every curve, and Nina had plenty of them, especially her big, round ass. Jessie could only hope to look that good when she was Nina’s age.
At the end of the interview, Nina said, “I like to keep a nice, warm working relationship with all my employees.”
Jessie leaned over and picked up her portfolio. She said, “I’ve got some papers here, actually, if you want to go over them with—”
“There’ll be plenty of time for that later, ” Nina interrupted. “I think a little conversation will be just fine right now.”
Jessie’s heart skipped a beat. Did Nina just say the word, later?
As in, ‘I’m going to hire you, so there’s no need to talk now because we can talk later?’
Jessie was having a difficult time trying not to shout for joy as Nina stood and asked if she would like some coffee. “Yes, please, ” said Jessie.
“How do you take it?”
“Black, two sugars, please.”
Nina excused herself to get the coffee. Jessie took a deep breath of relief. Her persistence was finally going to pay off.
She started looking around Nina’s house, which was where the interview was being held. It looked good. It was nicely decorated.
A smile surfaced on Jessie’s face as Nina was handing her the coffee. Maybe one day she would own something like this. Maybe one day she would be the sexy older woman welcoming a struggling younger version of herself into her empire.
There was a brief moment of silence. Jessie took a sip of coffee. Nina was staring her up and down.
As soon as Jessie removed the cup from her lips, Nina said, “So, do you have a boyfriend?”
She almost said yes, but then she remembered that she and her boyfriend weren’t together anymore. “No, I don’t. Not at the moment, ” she replied.
“A girlfriend perhaps?”
Jessie giggled. “No, I haven’t got a girlfriend.”
Nina let some thoughts run through her mind as she watched her sipping her coffee.
“Have you ever been with a woman?” Nina asked.
“I haven’t really thought of it, actually, ” Jessie lied.
The lie was very unconvincing, of course, so Nina’s next question came as quick as the smirk on her face.
“Would you like to see my Rumpus Room?”
Nina led her to a room on the same floor in the rear of the house. It was a large room with white walls and a king sized bed. The bed was made up in black and white bedspreads and a zebra-striped comforter. It was nice-looking room, but Jessie didn’t understand why she was showing it to her.
It’s very nice, Mrs. Hartley, ” she said.
“Yeah, I’ve had a lot of good times here, ” said Nina as she took her suit jacket off. “It’s my favorite place to relax and get rid of the stress of the day.”
Nina climbed onto the bed, tapped the space on the other side, and said, “Sit next to me.”
Jessie was dumbfounded, but she obeyed. When she was in a comfortable sitting position, Nina asked, “So you’ve never been with a woman?”
That’s when Jessie figured out why she wanted to show her the room.
Nina wanted to fuck her.
She had leaned in closer and was rubbing Jessie’s thigh. She looked her up and down like she was a piece of meat, but she was sensual and made sure not to move too fast so not to scare Jessie off.
Jessie smiled at her and started blushing. Answering Nina’s question, she said, “No.”
Nina kissed her hand and said, “Well, welcome to the firm.”
“Thank you, Mrs. Hartley.”
Nina grinned as she kissed her hand a second time, then turned it over and kissed her wrist. She slowly started kissing her way down Jessie’s arm until her mouth touched the cotton of her sleeve.
She gently grabbed the back of Jessie’s head and pulled her in for her first girl-to-girl kiss. Jessie felt awkward at first and her lips were tense because of it, so Nina slid her mouth around to the left side of her neck and started sucking and gently biting it. Nina heard a low moan come from Jessie’s mouth, so she bit her again and allowed her warm breath to pass over the moisture on her neck.
Jessie’s pussy was almost as wet as Nina’s now. She was happy about the job. She was flattered that another woman would take such an interest in her.
She looked at her with genuine desire and admiration and leaned in for another kiss. This time it was longer, more passionate, deeper, hungrier.
Jessie’s legs began to separate as Nina helped her get her blouse off. Then she took her own blouse off.
They took their skirts off next, leaving them in bra, panties, and stockings. In between some affectionate touching and passionate kissing, they took everything else off, leaving them naked.
There wasn’t an ounce of fat on Nina’s body. Nina’s breasts were firm and perky, sitting up right. Her hips were slender. Her ass was shapely and toned. It was like Jessie was looking at herself, only older, but the same body.
Once Jessie was on her back and out of her panties, Nina lowered her head between her luscious thighs. Jessie felt a rush of excitement. She loved having her pussy eaten, but her ex-boyfriend never wanted to do it. She raised her legs high and wide. She let out a sigh of relief as she felt Nina’s long tongue slip between her wet pussy lips.
She licked the hole for a while just to tease Jessie. She knew where the most pleasure from licking the pussy came from, and after a few seconds, her tongue found its way up to the protruding nub.
Nina got it wet with her tongue and lapped up pussy juice to spread over it. Once it was soaking wet, she closed her mouth around the clit and started sucking it while letting her tongue slither all around it.
Jessie was quiet so far, but Nina could see her legs trembling slightly out of the corners of her eyes. Her young apprentice was enjoying her first lesbian sex thus far.
Jessie’s mouth was wide open and she was quietly gasping for breath. She was gently squeezing the pillow and sometimes fondling her own breasts. She clenched her teeth from time to time.
This let Nina know that Jessie was the type who was too insecure to let herself go during sex. She was intentionally trying to keep quiet.
She wanted to see Jessie really cut loose. She wanted to bring the wild slut out of her and she wasn’t going to stop until she did it. Her pussy was tingling more just from imagining it in her head.
She slipped a finger into Jessie’s wet cunt, then two more and started masturbating her. Jessie started playing with her clit. She worked her fingers deeper until they were buried to the hilt.
“Oh, god, ” whispered Jessie.
Nina smiled on the inside and started working her pussy a little faster. Jessie’s legs were trembling more and her breathing was getting faster all the time.
“Ooh, ” Jessie said, still just a shade above a whisper.
“Yeah, ” replied Nina.
“Oh…oh…ohhh” whispered Jessie.
Nina stopped fingering her after a couple more minutes and held her fingers upwards while they were still in Jessie’s cunt. Jessie was still stroking her clit, and since Nina was holding it in place (from the inside), the tingles felt a lot more intense.
Leg spasms were coming more frequently. Moans were getting louder.
“Oh, oh!” moaned Jessie. Her vaginal walls spasmed. Her body convulsed as warm pussy juice started squeezing through Nina’s fingers.
“Ohhh, god!” continued Jessie when she felt Nina’s soft lips touch her pussy. Nina licked and tongued her clit, then came up and started kissing and sucking her mouth and neck.
Jessie’s body was really alive now. “Oh, it’s so good, ” she said.
She wrapped her arms and legs around Nina and held her close. She loved the feel of female flesh, the way her breasts pressed against her own.
Now it was her turn to try eating pussy. They both sat up. They kissed and gazed into each other’s eyes like animals in heat.
Their lips separated. Nina moved to the side. She slowly bent over so far that her head touched the bedspread. Jessie was left with the sight of Nina’s round ass sticking up in the air with her puffy pussy lips poking out in between them.
Jessie touched her ass softly and stared at Nina’s glowing wet pussy lips. She leaned forward with her tongue sticking out and placed it directly on her asshole.
“Oh!” said Nina, partly because it felt good, but mainly because she wasn’t expecting it.
Jessie wasn’t expecting it either. She was planning to lick her pussy, but for some reason that she did not know, she went straight to her asshole and started licking that.
Then she flicked her tongue on Nina’s pussy and slid her tongue from clit to asshole. She kept repeating this process but every now and then she’d stop at the pussy hole and suck at its nectar as she listened to Nina screaming and moaning her approval.
“Oh, that’s very good, ” whispered Nina. “Oh, ooh, oh, that feels good. Don’t stop.”
For somebody who had never been with a woman, Jessie could eat pussy really well. Nina was beginning to wonder if she was being honest about her sexuality.
She started fingering her cunt so she could focus more of her tongue action on Nina’s asshole. Nina was shouting out like crazy and she jerked and squirmed around as one intense orgasm after another shot through her.
She lost all the strength in her body and her pelvis fell to the bed. She was seeing stars. When she couldn’t handle anymore, she rolled over and kissed Jessie’s hand. She was happy to see that she was satisfying her new boss.
Nina giggled loudly, grabbed hold of Jessie’s face, and gave her a playful kiss. “Ummm, ” moaned Nina, and the kiss got slower and deeper with every passing second.
Nina got off the bed and pulled a strap-on from the closet. She put it on.
Jessie thought it looked odd. There was a pretty woman with huge breasts and big red cock standing in front of her making lovey-dovey eyes at her. It looked kind of silly at first, but it didn’t feel silly once Nina put it inside of her.
It was long and thick and it felt just like a real cock but without the heat. Nina fucked her with long, circular strokes, pulling the cock back so far that just the head was left inside of her and then slowly, but forcefully, grinding it back in.
The strap-on had a center strap that fit between Nina’s pussy lips and rubbed her clit as she moved. It was just as stimulating for her as it was Jessie.
She started pounding Jessie’s cunt. She had the whole bed rocking.
“Ooh, oh!” Jessie screamed. It was so good, almost like having a man in her sweet hole.
Nina pulled her up and lay down so Jessie could ride her. She noticed the expression on Jessie’s face had changed. She was really into it now. She wasn’t as nervous and she wasn’t trying to keep quiet anymore.
She arched her back started bouncing her sweet pussy on the strap-on. “Oh, that’s good, ” she hissed. “Fuck, yeah!”
Jessie got up. Nina asked her to suck it. She tried but it wasn’t real. She couldn’t get into sucking a fake cock, so Nina turned her around, licked her asshole and shoved it in her from behind while she circled her asshole with her thumb.
There’s no sight so pretty as the back of a woman’s head while you’re drilling with a strap-on, Nina thought with a wry smirk.
“You like my finger in your butt?” she asked.
“Uh-huh, ” responded Jessie.
She let it slip half way in. Jessie moaned and arched her back. Then Nina started fucking her hard and fast.
This was new to Jessie too. There had never been anything in her ass. She had seen it in porn movies, but it didn’t seem like anything she would want to try.
Having something in her ass and pussy at the same time was giving her pleasure galore. Cum was splattering from her cunt all over the strap-on and Nina’s pelvis.
“Oh, yeah!” hissed Jessie. “Fuck me! Yeah!” Jessie looked over her shoulder and said, “I’m really starting to like this job.”
Nina grinned, but didn’t respond. She was too caught up in her role as the man. She liked fucking women with the strap-on. It gave her a taste of what it was like to be her husband when he was fucking her. The power was a hell of a rush. She even had her shoulders squared like a man.
“Oh, god, that feels so fucking good, ” screamed Jessie.
“I’m about to cum.”
Jessie closed her eyes. Her face twisted into a passionate grimace. The tingles in her cunt were building with every thrust into her. Her head was bucking and her breasts were jiggling like mad.
“Yeah!” she screamed. “Ooooohhhhhh!”
Jessie’s body shook. Cum was spilling from her pussy. Her vaginal walls were spasming. Her legs were jerking. Her eyes had rolled into her head.
“Oh, fuck. Oh, shit, ” she moaned.
Nina was kissing her back and holding her closely throughout it all. She waited patiently for Jessie’s orgasm to subside.
When it did, Jessie said, “It was so hot that you made me cum twice.”
Nina started licking her ass again. Then she sat up and said, “Just wait ‘til the Christmas party.” She kissed her new intern one more time and they got dressed.
Jessie had needed guidance for her career, a new lover to take her mind off the old one, a new friend to replace the one who was moving out of town. In a matter of 30 minutes, this woman had managed to give her everything she needed to make her life happy again.
For the first time in a long while, Jessie felt something that had been evading her for months. Joy.