Matchmaker

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Ann Douglas
Ann Douglas
3,179 Followers

"You mean like sex toys?" Monica asked in reply, not really thinking she was talking about Barbie dolls and such.

Heather nodded her head in affirmation.

"I guess as much as the next girl," Monica laughed. "I mean, I have a vibrator in my night table," she added, thinking that Heather was asking if she had any.

"I was thinking along the lines of something a bit more intimate," Heather said.

Monica's response was a confused expression; what could be more intimate?

"Well, have you ever..." she started to ask in a normal tone of voice, pausing for a breath before leaning down and whispering the rest of the question into Monica's ear.

"Omigod, I've never done that," she answered, her look quickly transforming to one of surprise.

"Ever thought about it?" Heather asked.

Monica didn't answer immediately; instead she turned the question over in her head a few times. After she had, she had to admit that it was something she had sometimes wondered about. Like with oral sex, she had listened to her friends and sisters talk about how much fun it was, but after the disappointment with Bobby, had never been curious enough to take the next step. After discovering that it was all a matter of being with the right person, well, in her case the right gender, the opportunity never presented it self.

"I guess the answer would be, yes I have," she finally replied.

"Enough to think you might want to give it a try?" Heather continued.

"Well, even if I did, where would we get something like that?" Monica asked in turn, the practical side of her mind asserting itself.

In reply, Heather smiled and turned her glance to the far side of the room. Monica followed her line of sight until she spotted the small carry bag that Heather had draped across her shoulder when she'd first arrived.

"You're kidding..." she said. "Are you telling me that you actually carry something like that around with you?"

"Well, I was on my way to the club..." Heather replied, her smile growing broader.

That told Monica two things. The first, the probable reason why Heather hadn't been wearing any underwear - it would only have gotten in the way - and secondly, she now had a good idea what Isabella liked, even though she had never met her.

"So what do you think?" she heard Heather ask, bringing her back to the question at hand.

"I'm not sure; this is all happening a bit fast," Monica said after a few more moments of reflection, her voice of reason now being joined by that of caution.

"That's fine; it was just a thought," Heather said in half a heartbeat, quickly walking back her suggestion and hoping she hadn't gone too far in making it.

"I'm guessing Isabella likes it," Monica said, curious about whether she was right in her assumption.

"Actually, she loves it," Heather answered, "but that's her. It's not for everyone. Like I said, it was just a suggestion. Why don't we just forget I even made it?"

"But you did, so I have to think it's also important to you," Monica pointed out.

"Not as important as I think you might be," Heather countered, again hoping she hadn't ruined things.

Monica smiled, taking a few moments to think about that, and then said. "You know, I used to have a friend that always told me that, unless you are really sure that you won't like it, or it was really bad for you, you should try everything at least once. Otherwise, how will you know if it's not for you?"

What Monica didn't mention was that the friend had been Sarah Edwards, her first girlfriend and the one who had taken her Sapphic cherry. If it hadn't been for her, she might have just followed social convention and taken the same path as her sisters - despite how miserable that might have made her.

"Are you saying..." Heather asked.

"I guess I am," Monica replied.

"Are you sure?" Heather asked, a mix of hope and hesitation in her voice.

"Sure, why the fuck not?" Monica laughed. "After all, you only live once, right?"

"What was it I said before?" Heather asked, a grin on her face. "Oh yeah, girl, I do like the way you think."

-=-=-=-=-

"Oh God yes, fuck me!" Monica cried out as the faux cock pressed deep inside her once more. "Fuck me, Heather, fuck me harder!"

When Heather had first produced and then strapped on the admittedly realistic phallus, it had taken all of Monica's will power not to laugh. Despite some of the manly traits the former sports star exhibited, the sight of her with a dick dangling between her legs seemed so incongruous as to be laughable. Especially since the object in question made her more endowed than any man Monica had ever seen - not that that number was more than the fingers on her hand.

But she was determined to give it a try and laid back on the couch according to Heather's instructions, spreading her legs as the now packing blonde climbed between them. Monica had been penetrated before, by fingers, her aforementioned vibrator and even once upon a time, a toy not dissimilar from the one now poised before her womanhood. But the latter two had been controlled by her own hand, with the limitations thereof. To have someone enter her as Heather was ready to do was unexplored territory indeed.

Despite Heather's assurance that the female body, especially one that had already been well prepared by their earlier play, could easily accommodate something of the toy's size, Monica was relieved when the older woman produced a tube of lubricating gel from her bag and generously coated the rubberized cock with it.

"Ready?" Heather asked as, her hand tightly wrapped around it, she placed her cockhead against the entrance to Monica's pussy.

"Yes," Monica said, hoping the lie wasn't too apparent.

"Just relax," Heather said as, with a firm press forward, she slowly slipped the cock half way into Monica, pausing for a moment before sliding it half that distance back.

She repeated the motion a few more times, both to assure Monica that, yes, she could easily accommodate its length and also to let her feel the effect it had on her body as it passed in and out. An effect that she discovered could be quite pleasing.

It wasn't long before Monica was comfortable with the full length of Heather's cock, along with the increased speed of her thrusts. With their bodies pressed tightly together, they again began trading kisses. Breasts rolled against breasts, adding to the pleasing vibrations radiating between the two of them.

Despite the novelty of it, it soon seemed to Monica the most natural thing in the world. Which, after all, was what nature had in mind for the female body. It had taken human ingenuity, however, to make it possible for the younger woman to enjoy the act with the gender of her choice.

Wanting to penetrate Monica even deeper, and bring the additional pleasure she knew that would bring, Heather took hold of both Monica's legs and lifted them high enough for her ankles rest on her shoulders. Then, with her hands tight against Monica's hips, she began to fuck her even faster. As good as that was, the younger woman wanted even more, crying out the need that filled her. A need that Heather was happy to fill.

Back and forth they rocked, sweat running down their bodies as they formed a sexual symbiosis. The conduit that joined them might have been artificial, but had been carefully designed to bring simultaneous pleasure to both. A small extension, situated against Heather's clitoris, allowed her to partly share in the constantly increasing pleasures she was bringing Monica. Added to that was the emotional gratification she felt that helped make up the difference.

She could feel Monica's body responding to her efforts, but still she wanted her to have more. After one more strong thrust forward, she pulled all the way out of the younger woman and turned her around so that she was now bent over on all fours facing the arm of the couch she had previously been laying against.

With complete ease, Heather reentered Monica from behind, taking a firm grip on her waist that allowed her to pull the younger woman back on each forward motion, adding to the depth and effectiveness of her actions. The air filled with a seemingly never-ending series of moans - the volume and frequency of such matching the increase in Heather's attentions.

Feeling that Monica, and to a lesser extent, herself was near to the end of their journey, Heather reached down under her body and, with outstretched palms, cupped the brunette's ample breasts, gripping them tightly as she pressed her own against her back. They had become almost one body, with one purpose - now so very close.

"Oh yes, oh yes..." Monica panted, her words cut short as resounding waves of orgasmic delight exploded from deep within her. The force of the eruption such that it drained just about everything from her, causing her body to collapse from a wondrous exhaustion once she had given all that she had to give.

Heather's climax was far less dramatic, but nonetheless pleasing, filling her with a sense of serene accomplishment. She dropped back onto the bed next to Monica and, closing her eyes, wrapped her arms around her as they both soon drifted off to sleep.

-=-=-=-=-

The new day had well begun by the time Monica opened her eyes to greet it. The excitement of last night's frolic still filled her with a pleasing warmth, one that brought a generous smile as she turned her head and saw the equally nude woman sleeping beside her. For a brief moment, she had worried that, when she looked, she would find herself all too alone.

'It's nice to know it wasn't a dream,' Monica thought as she reached out and, with the gentlest of touches, ran the edge of her fingers against Heather's cheek.

The light caress proved enough to cause Heather's eyes to open, blinking twice before Monica came into focus. The welcoming smile was duplicated as she took the brunette's hand in hers and tenderly kissed her fingertips.

"Good morning, beautiful," Heather said, leaning close enough to plant a gentle kiss on Monica's lips.

Monica shared a kiss of her own, then backed just far enough away for the two of them to sit up in the bed. It was a tight fit, but neither seemed to mind.

"Do you have plans for the morning, or can we spend it here in bed?" Monica asked, a part of her hoping that the latter would be the case.

Heather paused, seeming to be thinking about it.

"Actually, I do have something to do this morning," she said apologetically.

"You can't blow it off?" Monica asked hopefully.

"Not really," Heather replied. "You see there's this girl..."

"Oh," Monica interrupted, her buoyant bubble suddenly bursting. She knew that the woman beside her was a player going in, and that last night, as momentous as it had been for her, might have been just another Friday night for Heather.

"...and I'm really hoping that she's going to turn out to be more than just a fuck buddy," Heather continued. "So I figured taking her out to breakfast this morning might be a pretty good start. So how about it, baby, you hungry?"

It took an equally long moment for Monica to react.

"You are so evil," Monica said in a mock angry voice.

"Honey, you have no idea," Heather grinned, "but trust me, you're going to find out."

"In that case, I'm ravenous," Monica laughed.

"Good, 'cause I call first dibs on the shower," Heather replied. "Remember, I've had experience with the plumbing in this old place too," she added with a laugh.

"We could always share the shower," Monica offered suggestively.

"That we could," Heather replied, a smile filling her face at the thought, "but I'm pretty sure if we did we'd miss lunch, never mind breakfast."

"This is true," Monica smiled back, coupled with a hand gesture of capitulation.

They kissed once more, then Monica slipped out of the bed and looked for her robe, forgetting for a moment it had been left out in the living room.

"I'll be right back," she said to Heather as she walked naked into the outer room.

Standing in the middle of the living room as she wrapped the robe around her, Monica was about to head back to the bedroom when there was a loud knock on the door. Not as insistent as the one she had answered last night, but loud enough that she really couldn't ignore it.

"Sylvia?" she said in surprise as she opened the door and found the older woman standing there, a large breakfast tray in her hands.

"I thought you might be hungry," Sylvia said, glancing down at the tray of eggs, toast, orange juice and sausages, an abundance compared to what Monica normally had in the morning.

"Sylvia, this is too much," Monica said automatically.

"Well, it is breakfast for two," Sylvia clarified as she stepped inside and walked over to the countertop to lay down the tray.

"Two?" Monica repeated, wondering for a moment if the her landlady was planning to join her - which would indeed be awkward considering who was waiting just a half closed door away.

Thankfully, that didn't turn out to be the case as, after depositing the tray, Sylvia turned and headed right back for the door.

"Enjoy it, my dear," Sylvia said as she opened the door and stepped back out into the hall.

So intent was Monica in watching Sylvia leave, she hadn't heard Heather come out of the bedroom and come up behind her.

"My, that does smell good, doesn't it?" a still naked Heather said, stepping past Monica to get a better look at the goodies on the tray.

"Oh my God, Heather," a startled Monica called out as she realized that Sylvia's great-niece had to have come out of the bedroom before the older woman had fully closed the door behind her. "What if she heard, or worse, saw you?"

"I don't think she would've been shocked, or even surprised," Heather grinned as she picked up a piece of toast and nibbled at the corner. "After all, she did make a point of saying this was breakfast for two."

"You didn't tell her that you were coming back here, did you?" Monica asked, feeling a tinge of embarrassment at the prospect.

"No," Heather quickly answered.

"Then how...?"

"Remember when I said my Aunt has a bit of a reputation as the family matchmaker?" Heather said after taking a second bite.

Monica nodded her recollection.

"Well, what I didn't tell you was that she rarely ever gets it wrong," Heather smiled.

Monica still wasn't sure how she felt about Sylvia knowing what had been going on over her head all night, or at least could make a good assumption about it, but she did manage to form at least half a smile.

"Look at the bright side," Heather said as she now started to add other items from the tray onto one of the small plates. "Not only do we now have breakfast, but we also have the time for a long shower afterwards."

That, Monica thought, was a bright side indeed.

END

Ann Douglas
Ann Douglas
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14 Comments
ChumulyaChumulya6 months ago

Loved this story.

kathy2012kathy2012over 2 years ago

Hot! Hot! Hot! I was flowing like a river! Rimming, Strapon, Doggy style! Breakfast in bed! Loved it!

Best regards,

Kathy

alexwatson62alexwatson62almost 5 years ago
SO SORRY BUT ...............

...... I must admit to almost having run out of superlatives to describe how much I admire your work.

Your stories don`t follow a "winning formula", rather each individual story stands on its own merit, and that is rare.

Congratulations.

AnonymousAnonymousover 6 years ago
Hilarious!

You had me laughing out loud. Such a great story!

HiddenInTheOpenHiddenInTheOpenover 6 years ago
Another really good story!

I totally enjoy your stories, and eagerly look forward to each new one as it comes out. Thank you so much for sharing them with us!

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