New and Improved Olivia

My breasts hung a little lower than they used to, although they were still somewhat firm. Richard used to practically worship my breasts. My belly was not completely flat, but the slight roundness was I guess a little more feminine. Sensual even. My legs were still slender. Long.

My face sported more lines than years ago, but I had taken care of my skin with lots of product assistance, so it was more of the creamy variety. And being a natural light blonde meant that my skin was always fairer. Astrid must have chosen green because of the flecks of green in my otherwise hazel eyes, which made me happy that she actually noticed the nuances of my eye color.

She caught me checking myself out. "I knew I'd convert you to nudism eventually!" She laughed at her own joke. . or semi-joke maybe and tossed me the green sports bra.

"Of course I will need to find some replacements for these things," she pulled at the waistband of my very vanilla panties. She eyeballed my lower half, causing more blushing, nodded and headed out the door. "I will be back shortly."

I took a deep breath and started to put on the bra, pulling the tight material down over my breasts. Snug but comfortable. My breasts would not move much in the tight fit. I glanced around and found a tank with deep cut arms. This would also be outside of what Olivia 1.0 would wear, but I pulled it on anyway.

I was still without any pants but I looked at myself in the mirror, focusing on the waist up. It looked cute on me. I actually liked it. I didn't look like an older woman trying to appear young, but rather a woman who just was having fun. And since Olivia 2.0 was all about having fun, this worked. I smiled at myself.

I heard the door open and Astrid came rushing in. "Ooooo. Cute!" She quickly appraised me and smiled.

"Of course you would make anything look great!" She then quickly shoved a set of panties into my hand. Actually, a sport thong. I had managed to go 37 years having never worn a thong, and yet here was Olivia 2.0 considering it.

I sighed. All part of the process. At least that's what I told myself as I shimmied out of my standard but very safe and comfortable panties. Astrid just watched me, which really unnerved me. She actually looked like she was going to say something but then just pressed her lips together. I imagined it was some sort of criticism so was very glad that she didn't speak.

I quickly pulled the thong up and felt the fabric invade the space between the cheeks of my bottom for the first time. I had experienced the occasional inadvertent wedgie but this was pretty intentional and fully invasive.

I looked around for the black workout leggings I knew she wanted me to wear and quickly pulled them on. I then turned towards her and the mirror.

"You. Look. Fantastic." She just grinned from ear-to-ear as she stepped forward and just hugged me.

At this point in our rather brief but intense friendship I had not exactly gotten used to her very physical way of interacting. Not yet. But I was maybe one step further down the path.

Even if the hugging, hand holding and general touching still remained foreign to me, I understood the heart behind it. And that was lovely. I could easily accept something unusual if the person did it for loving and kind reasons. And with Astrid it seemed everything was lovingly done, coated in care. She was compassion personified. God, I needed her when she fell into my life.

So, she made me wear my new workout gear out, which consisted of tighter clothes than I had ever worn with more gaps and skin showing than I had ever felt comfortable showing. But with Miss Perky at my side I felt just . . . happiness. Kind of like I didn't care. Because I don't think I did. Olivia 2.0 was really cooking.

++++++++++

Four weeks of aerobics with heavy doses of Astrid between does wonders for a healthy heart. We talked every day and had averaged four dinners or lunches a week for the whole month. I hadn't felt this happy in over a decade, maybe longer.

Astrid continued to push me out of my safe zone, sometimes very subtly where I didn't even notice until too late. I found myself being introduced to all sorts of people wherever we ended up. She knew everyone, or would by the time we left.

But sometimes she pushed me rather obviously.

One night I went to her apartment for dinner. So far any dinners consisted of general normalcy: great healthy food, wonderful conversation that lasts hours and hours before we even realize time has passed. On this night things were slightly adjusted.

I let myself into her apartment per usual, spot on time, but apparently, Astrid still wasn't ready. Or something. Astrid was naked but a thong when I arrived.

Now Astrid had managed to get me out of clothing on a few occasions on our shopping trip, but besides seeing her in her workout gear (looking pretty amazing) this was a first. And she looked like a greek goddess.

"Hey there . . . Astrid." She smiled from behind the kitchen counter and came straight to me as if nothing was different, embracing me in a warm hug . . oh yeah while still naked. My hands uncertainly held her back as she fully hugged me. Yes, with Astrid everything seemed to be a new experience.

She turned and took her perfect bottom back to the kitchen. "Sorry, laundry machine was acting dodgy so my clothes will be ready in ten minutes. Hope you don't mind."

"Um . . . sure . . . " She glanced back at me as she got back to mixing the salad and smiled.

Sometimes I wondered if she was oblivious to some forms of discomfort or if she simply did not care.

She went back to her salad and I tried to seem casual and not stare at her physical perfection.

She noticed.

"I am sorry, I am making you very uncomfortable." She came back from around the counter. "I will find a robe or something . . . " She began quickly heading towards her bedroom

"No, no. It's ok. It's . . . different." I smiled at her. "I think it is . . . um . . . I think it is good for me. Maybe."

She nodded, shrugging. "Of course it is good for you." She stood in front of me, her hands on her hips, her head cocked to one side. "Have you ever tried it?"

I was very scared to answer. Anytime I answered something like that question from Astrid it ended up with me doing something very uncomfortable. To be honest, the outcome was always good, but the journey to get there was wrought with anxiety.

But this was Astrid, so I kept the line of conversation going because I knew she would never let up. "Tried what?"

"Just stripping down, of course." She smiled, leaning back against the kitchen counter. Her fingers grasped the edge and she leaned her uncovered behind against the edge. Her perfect stomach still perfect even as she leaned against the counter. No angle was bad for her.

I shook my head. "Changing, bathing, sex. Otherwise Liv usually remains dressed."

"Why?" She crossed her arms under her naked breasts, entirely too comfortable with being naked.

"I . . . uh . . ." I actually didn't know. "I guess . . . I feel more comfortable . . . in clothes . . ."

"Why?" The corner of her mouth quirked up. I knew this was her amused smile. Not amusement at my expense but rather amused at me as I grew a little more working through something . . .

"I guess I am . . .well I guess I am more used to it."

She nodded. "Probably." She didn't move from her spot. "So you could get used to not wearing them, hmm?"

"Maybe?" I then laughed as I had no idea.

"Well I think you should. . . " She moved back around the counter to work on the salad.

"Should do what?"

"Strip down!" she exerted with mock exasperation.

"Um . . . now?"

"Hmm . . . hadn't thought of that. Good idea!"

Dammit.

"Listen Astrid, I am not as comfortable with this," I motioned in a circle indicating my body, "as you are with that" motioning at her body.

"Why?'

"Well I . . . I don't know. You are like a gorgeous chiseled goddess with a perfect ass and I am . . . Liv."

She grinned at me. "You like my ass huh?"

"Astrid!"

"Ok, I get it. Here's the thing . . . " She came over and did her famous holding-my-hands thing, "I think you are gorgeous. I have seen all of that," she let go of my fingers to motion at my body, "and it's pretty awesome. So, you wearing clothes or not wearing clothes doesn't matter. You look amazing in both states of dress."

And with that she shrugged, grinned and grabbed a carrot, munching on it as she finished tossing the salad . . . still nearly naked.

Surreal.

So, I struggled. The new me shouldn't be upset by what the old me held onto. Why would I not want to be naked in front of others? Shame? Embarrassment? In Astrid's case, comparison? Inferiority? I think all of those were probably very good reasons generally speaking, but honestly I didn't want to feel shame or embarrassment or inferiority anymore. I wanted to feel confidence and self-assurance and independence and pride. I wanted to feel like I had nothing to hide and everything to show. And screw anyone who didn't like what I opted to do.

The problem was that I was not ready for that leap. Maybe I needed to do it one small step at a time. A baby step.

"Are you going to stay dressed like that?" I usually was not this direct so my question took Astrid a moment to register. She smiled and nodded. "Sure . . . unless my boobs offend you."

I shook my head. I felt determined. And somewhat empowered. I got to make a choice here. And sure, Astrid pushed me a bit but I was the one in control of me. And I chose to take a set forward . . . or out of my clothing anyway.

I took a deep breath and then grabbed the hem of my sweater, pulling it up and off. I then unbuttoned my shirt and slipped that off my shoulders.

"I choose to stop undressing at this point tonight," I stated, as if I was reading from a scroll. I then felt like such a dork.

Astrid had been just watching me with an excited smile spread across her face. She nodded at my proclamation. "As you wish, Liv . . ."

She looked like she was going to burst. I laughed, knowing exactly what she wanted to do but knew that she was holding back for me, and spread my arms. She giggled and ran over to give me a big hug. It's what we do now.

And I felt as naked as Astrid that night. At least for the first twenty minutes, then I forgot to think about it.

++++++++++

"How did I let you talk me into this?"

"Well, for starters, I promised you a super cute guy, and you know that Astrid always delivers on her promises!" At this point she was doing her final inspection of me. Yes, I let her advise me on a dress. And my hair. And my makeup. Honestly it felt like highschool all over again. But also, it was pretty fun.

"So you usually go out with guys you meet at the gym?"

She shrugged her shoulders as she did the final adjustments to her hair. "The cute ones yes."

"And is Mr. Cute Guy aware that he is to be on a date with a more 'mature' woman?"

"Yep! And he knows you will be there too!" She laughed at her own joke, which just caused me to smile.

"Listen, he will think you are smokin' hot . . . and yes he is aware you and I are a little different aged . . . but both guys are pretty hot so you can pick either one."

And yes, they were both unbelievably attractive. I am pretty sure both were pretty much interested in Astrid, but they both were very pleasant, and complimentary, and one was even pretty funny. I liked funny. Rick pretty much become the opposite of funny, whatever that was, in his last few years with me.

Jonathan (the really funny one) seemed to enjoy my company, and started getting pretty flirty. It could have been the alcohol, but I liked to think it was because he was enamored with my great looks and charming inner beauty.

I glanced at Astrid, who seemed to be barely paying attention to Greg, the other one. In fact, she was just smiling as she watched me. I am 90% sure this whole night was about getting me laid and had very little to do with her at all.

That's why she spent most of her time focused on dressing me up. That's why she essentially let me 'pick' which guy I wanted. That's why she steered all of the conversation towards me. And that's likely how she was able to maneuver Jonathan into being flirty with me. She was like the Wizard of Oz, pulling lever after lever behind a curtain to orchestrate this entire thing.

And here's the thing: the old me would have been very offended that she had done this, thinking that I could not do this on my own. And maybe I couldn't. Damn the guy was super-hot and was ALMOST young enough to be my son. Not quite, but getting there.

But the new Olivia? Well she appreciated friendship over pride. She didn't let other people's opinions drive her. She was comfortable in her own skin (or at least her own skin covered by some underwear. . but she was getting there dammit!).

And so, I decided. I was going to probably fuck Jonathan. Why? Because he was a gift from my awesome friend Astrid, who I had grown to love dearly. And she wanted me to be happy. And also, because I hadn't had sex in quite a while. And also, because he was very very hot and having his hard-muscular young body rocking between my thighs could really be an amazing experience.

++++++++++

So, that was how I found myself making out with Jonathan on the couch. Jonathan with the very cute face and tousled hair. Jonathan, the 21-year-old guy built like an Olympic swimmer, his lean body and muscular chest now shirtless. Jonathan, his strong hands gripping my side as he pushed his hard body with something very noticeably hard against my stomach.

And on the couch across the room, Greg was desperately trying to get Astrid going but she seemed only interested in watching us. She let him cup her boob, kiss her neck and rub her thigh. But she didn't seem that interested. And he was catching on finally as he seemed disappointed.

I glanced over and saw her whisper into his ear. He looked a hair disappointed but then nodded. She smiled and literally, right in front of me, unzipped his fly and fished out a very hard cock. She then stroked him and returned to watching me. That came across as possibly the most bizarre but one of the hottest things I had seen. My recently discovered best friend stroking this young good looking guy's dick right in front of me.

Jonathan didn't even seem to be aware other people were actually in the room. He laid on top of me, his hands slipping up under my shirt, feeling the front of my breasts through my bra. I could feel the outline of his hardness pressed now against my lap, which felt pretty amazing. I rotated my hips, rubbing my pleasure center against him. Little tingles of pleasure spread all over my body.

I ran my hands down his shirtless muscled back. The boy was like a greek god.

I glanced back at Astrid, her hand moving faster now and Greg's rather large member seemingly straining in her grip. He looked pretty happy at the moment so I imagine the fact that he could not get much else was no longer a concern.

I felt Jonathan's fingers slip up under my skirt. Moment of truth: stop him now, let him continue here or get him to take me back to the bedroom? Olivia 1.0 would stop him. Olivia 2.0? I don't know. Is the new Olivia a little slutty? I am not sure having sex with a stranger in front of my friend and her date, no matter how blind her date had become, was the new Olivia.

I felt his fingers slipping up in between my thighs and brush across the front of my panties. Yep, they were wet. Why wouldn't they be? I glanced back at Astrid again, and now Greg just laid back against the couch, his head back and his half flaccid dick just hanging out in the wind. She was cleaning off her hand and just watching me.

I didn't know if the new Olivia was slutty or not, but I felt like I almost owed Astrid something for setting all of this up. It might have been the multiple drinks, but I figured I could do some stuff in front of her, if I wasn't completely exposed. So, I decided.

"My clothes stay on, but I want you inside of me. Now." And Jonathan smiled at me, seemingly happy at his newfound fortune. I felt his fingers pull aside the crotch of my panties, exposing my lower lips. Astrid couldn't see but I almost detected a tiny smile on her lips. She knew what transpired between Jonathan and me.

I felt him rummaging around with his belt. Suddenly his pants were down and a very large and fat cock was pressing into my body. Holy shit Rick was never even close to being that big. So, I cried out. Shock. Surprise. Lust.

His strong hands gripped my hips as he pushed hard into me. I usually liked more sensual starts, but honestly it felt amazing and I was in the mood for a pounding.

The width of his member stretched my lips and my walls around him. Each thrust sent tingles across my skin. My body actually deeply craved him at this moment. I wrapped my legs around his lower back and pulled him into me, each thrust going deep inside of me. His balls literally bouncing and slapping underneath me.

He and I grunted together, small moans intermingled. I glanced back at Astrid who just stared at me, a small smile on her face. Oh God, to know what was going on in that mind of hers. Why was she so obviously enjoying this so much? Maybe it was like live porn to her.

And so, Jonathan buried his face in the pillow over my right shoulder as his body moved so quickly against mine, bringing me closer and closer to a screaming orgasm. Greg, his face pointed skyward, continued to recover on the opposite couch from the orgasm Astrid had gifted him. Astrid, her face pointed directly at mine, and mine directly at hers, as I felt the coming waves. My body shifted quickly under Jonathan's constant movements.

She watched me intently. She seemed oblivious to the gorgeous specimens of men lingering around in various stages of undress, but instead seemed only interested in my face. And that both unnerved me and excited me beyond my understanding.

And that's when I felt my sexual partner unload into me. A lot. His long moan signaled an injection of serious amounts of cum inside of me. I wrapped my body around his, pulling him close, not wanting to lose momentum as he began to slow down. I was too close to lose it . . . And so I rubbed my hips hard against him, feeling my clit press against the base of his cock. I was close. Close. I looked at Astrid as I finally felt the explosion, desperately holding onto Jonathan so that I could finish. And Astrid's face became this sweet smile as I know that my orgasm face twisted and strained, the waves crashing over me. I couldn't control the long moan during my release.

What was our connection? Was this normal for other people? I didn't understand any of this. As physically perfect and somewhat sweet and funny and charming as Jonathan was, I really found myself focusing on Astrid, who was focused on me over the hot guy sitting next to her. Confusion came on to me.

But my mind had nearly blanked out during the orgasm, so this wasn't the time to really figure this all out.

I slipped out from under Jonathan, who had practically passed out. We were at Astrid's place and both guys seemed to be in states of semi-consciousness, so we left them on their respective couches.

"Please stay here tonight, Liv," Astrid whispered to me as I got my clothing sorted out.

I smiled and nodded. "Good idea . . . " It was late. I was feeling woozy and honestly the orgasm had wiped me out.

We both moved towards Astrid's bedroom, stripped down to our panties (yes, I was topless and mostly comfortable with it! Baby step!) and climbed into her bed.

I immediately felt Astrid's body snugly pressed up behind mine, her warm breasts pressed against my back. Her hand snaked around my waist, her fingers resting on my belly. She casually began to draw shapes around my navel, her fingertips just barely connecting with my skin.