Lesbian Lady Boss

I could feel my face getting red as I listened to myself but clearly, they were the words that she wanted to her as she switched from her teasing to fucking me at high speed. She wasn't as brutal as Lexi nor did she have the heavy hips of Roxy, but she was an expert with her angles and the head seemed to hit every spot inside me. She made me cum on all fours then spun me round onto my back and fucked me with my legs over her shoulders. By holding my legs in different positions, the strap-on entered in different angles touching places inside I never knew existed.

While on top of me, with her strapon inside me her phone rang, and she picked up her wife's call.

"Hey hun...no, just working out at home...yes please..bring us some wine...love ya."

Then she hung up as she continued fucking me. Then she looked into my face and must have seen the concern and confusion about the call she had just taken. She made that face that comedians do that say, "What?" and laughed as she said,

"You gotta leave soon babe...wifey will be here in an hour."

If I felt that Jill the insurance lady was a bitch, she was a hot funny bitch.

On the one hand, I couldn't believe how casual she was about talking to her wife while fucking me. On the other hand, she knew how to handle my body and was giving me intense pleasure. Maybe the wife knew about the other women, maybe it was the open relationship that Roxy talked about. I didn't have time to speculate further as Jill renewed her efforts, gripping my ankles as she ploughed into me. She was thrusting with a lot of passion; she wanted me to cum again and as I did, she pulled out of me and laid on top of me, smiled to my eyes "glad you needed a new insurance policy, babe". We laughed and we kissed, then she slapped my butt, "better get going hun".

I literally left five minutes before her wife came home and I couldn't help myself as I waited and saw her coming. They greeted at the door like lovers do and went inside. There were no shouts or the sounds of things being thrown, yet surely the wife would have spotted something. As I got dressed in a hurry Jill made no attempts to tidy up or make the bed, in fact, I wondered if she was still wearing the strapon when her wife came home. Maybe that was how it worked in this world.

I loved my time with Roxy. She cared, and actually invested time showing love and passion, and took care of me as her lover while we were together, but a few things didn't make for a "perfect match". She really wanted to show me off as her classy, rich girlfriend who had a high-level position, during gatherings, occasions, etc. I know she must've been proud of our relationship, but I felt like she was showing me off.

I think the lack of exclusivity, while agreed upon and desired by me, severely limited the relationship, especially since we were open about it. Yes, I was exploring and enjoying that, but it always felt different with her. On the other hand, she was a long time lesbian, so I felt her rate with other women was quite high. It may sound selfish, but that's how I felt.

Now, why did I not want exclusivity with Roxy since she was different, and I liked her? Well, I was not ready at all to start. The whole transition from straight to lesbian had only been ongoing for a few months, and during that time I had only been with three other women. Put aside being divorced after a long marriage, in a new city and a new leadership position with a ton of challenges.

I have to admit too, I liked women, a lot. I enjoyed the different styles, different characters and different things they offered. Maybe because I was with only one man for a very long time? Maybe because things were very stagnant, vanilla, meh forever with him? I wanted more. I wanted to try more, feel more, and live through more till I figured out who I was.

As our relationship grew with more time spent together, I liked her more. Did I worry about losing her? Yes, but again, I wasn't ready for a committed relationship. As I explored more, I was also seeing her doing the same with other women, so it felt like just a fun relationship and going with the flow, who knows where it may take us.

Roxy's involvement with other women didn't assist with being monogamous. Yes, we weren't exclusive and yes we agreed to that but still, I felt she wanted to do the same. She was a bit more open than I thought she should, maybe?

One night, I asked her if could stop by after work, she said sure but let me know she had 'guests'. I went and she had a gorgeous younger woman, in her early 30s.

She introduced her, "This is Bianca, she works in advertisement and social media, and she's helping with my new business expansion."

Maybe we were a little too open with these aspects? But I thought we had an understanding and agreement on how things will go. Was I jealous? I was. But I calmed myself down since I was doing the same. I stayed for a glass of wine, Roxy didn't ask me if I wanted to stay over, but either way, I really wasn't going to have a threesome with them. Not that she offered, but decided I wasn't if she had offered. I never had one previously, and our relationship wasn't there. We weren't a couple that planned such a thing.

I left, Roxy didn't text me the next morning, so I drove by her place after work and Bianca's car was still there.

When I met the insurance agent Jill it felt exciting, new, refreshing and added more to me.

Jill texted me a few days later, "Hey babe, my wife is on night shift this week, wanna come over and spend the evening?"

I felt excited...excited enough to tell Roxy I was staying late in the office and then going early to bed for an early morning meeting.

I rang the doorbell, and Jill greeted me in a red silk robe. She pulled me in, hugged and kissed me. She looked so sexy as she walked to her living area. "I see you came directly from work", she turned and looked at me, "did not want to waste any time, did not ya?". I blushed, she giggled, let her robe loose and I could see she was already wearing her strap-on. "Come in, we both know why you are here, so why don't you get ready."

I could feel my cheeks colouring as she had hit the spot perfectly and I could feel myself getting wet. I knew I was acting like a slut, but I wanted it, no frills sex, something simple.

"Going to fuck you first then lick you clean. And you know how I love the taste of freshly fucked pussy."

The way she talked was getting me hotter. She wasn't nasty or domineering, it was just a matter of fact statement, almost in the same way she recommended the best policy for her clients, tailoring it to their needs and wants.

I unhooked my skirt and let it drop to the floor and she laughed, "No panties I see, you knew you were going to get fucked so you came ready... now that's what I call an eager slut."

I went to bend over the arm of the couch but she stopped me,

"Woah there eager beaver, you need to suck this first, show me how eager you really are."

It wasn't the first strap-on I had sucked as both Lexi and Kayla loved me doing it and even Roxy had me choke on it on a few occasions. Dropping to my knees I caressed it like it was real and then took it into my mouth sucking it deeply. As a familiar taste hit my tongue, I stopped moving my head as I heard Jill chuckle. She answered the question I had yet to verbalise, but was pretty certain I already knew the answer.

"Yep, now you know what wifey tastes like."

I couldn't believe it; she must have fucked her wife before she left as I could still taste her.

"Now you taste her good," Jill said still chuckling as she started to move her hips in and out.

Should I have stopped? Been shocked? Maybe but instead, I let the plastic cock slide in and out drawing the taste further into my mouth. Then Jill grabbed me by the hair, not savagely as Lexi would have done but firmly enough for me to comply with her wishes. She turned me round, pushing me over the arm, so my ass was high, and my head and breasts were pressed to the seat cushion. Then as she poised ready to slam into me, she said something that made a mini-orgasm ripple through me.

"How would you like it if you were between her thighs right now? Tasting her freshly fucked pussy as I fuck yours."

I wasn't sure if she was seriously offering, suggesting or commanding, but the thought of it made me hotter than hell.

"Yes," was all I could moan.

"Good slut," Jill said and grabbing my hips drove into me burying the strap-on deep in me.

I was moved onto all fours on the sofa, ass up in the air as Jill was thrusting her cock inside me when my phone lit up with a few messages from Roxanne.

"That must be someone wishing you good night," Jill laughed as she slapped my ass and thrusted more. I felt some guilt hearing her words when reading Roxy's SMS afterwards, but that guilt disappeared when Jill came in with a glass of wine, sat and talked to me for a little bit, and then said "It's a booty call night, we aren't done, babe."

We moved into the bedroom and Jill laid me on the bed before climbing on next to me. My body was still sensitive from earlier so her touches made me shiver and moan.

"Time for you to do some work," she said as she reversed her position, so her knees were on either side of my head. Looking up I could see her wet pussy glistening with dew as she lowered herself onto my mouth.

It wasn't the first time I had licked another woman but normally they would be on their back as I licked them. This time Jill ground down into my pussy, riding my mouth as she almost masturbated herself against my lips. I reached to touch her but found her hand was already there rubbing her clit as she ground against my mouth.

When she came, I almost thought she had urinated in my mouth as there was so much fluid, but the taste told me that it was her juices, not urine. As she writhed on my tongue, I swallowed as much as I could while watching her twist her own nipples.

If I thought, she was finished then I was very much mistaken as she twisted through 180 degrees and almost forced my thighs apart. Not that they took much forcing, as they almost fell apart of their own volition. Her strong hands moved to my buttocks, lifting me off the bed as she began to lick, and tongue fuck me until it felt like my nerve endings were ready to burst into flames. I feebly licked at her pussy but was finding it difficult to coordinate my movements and was content with her grinding as she nibbled my clit. When she clamped her mouth over my clit and sucked, I nearly took off as I dug my nails into her ass.

When I finally came down to earth she laughed, "Hope you haven't left any scratch marks for me to try to explain to wifey."

My head was spinning a little as I dressed. "Did her wife know? Was her comments about a threesome just heat-of-the-moment sexual banter?"

I was spending more time with Roxy over the next few months as our relationship continued to grow. I believe the peak of my relationship with Roxy was when we travelled together. A few months into the relationship, she asked me if I wanted to spend a few days away together on a relaxing trip which excited me a lot.

She said it'll be her treat, and that she would take care of everything. I told her she didn't need to do that since we can share, but she said it's the only way she does this.

I remember her exact words, "I wanna take care of you."

She planned everything, the travel, the nice beach hotel in Florida, the activities, everything. I loved her fine taste already with the restaurants she picked in New York and the places she chose for us when we went out. So, this was a concentrated dose of luxury experience. It was also my first time travelling with a woman lover and the first time we got away since my divorce as a couple, yes, a couple. So, it meant a lot to me.

The trip was a lot of fun and relaxation. Beach, swimming, sailing, massages and nice restaurants. It was a lot of time with her in the first place, which I felt highlighted a high point in our relationship. The first day we arrived, it was late in the afternoon, we went for a dip in the pool, and then she told me to get ready for a nice dinner. Dinner was very nice, great ambience, superb food, and most importantly her being with me. I felt butterflies in my stomach walking back with her to the hotel with her holding my hand. When we got to the room, she changed into a nightshirt, as I came out from the bathroom and looked at her lying in bed.

"Babe, are you gonna sleep already?"

She laughed, "Why not?"

"I would not agree to that," then winked at her as I went on, "You should get a return for your investment."

Smiling she said, "Come here," tapping her lap as I straddled her.

As we kissed, she whispered, "Are you enjoying this?"

I looked into her eyes with love as I whispered back, "I am loving it."

She kissed me, undressed me from the new lingerie I put on for her, and laid me on my back then went down on me. Her tongue was like her, instant and powerful. Drawing it over my pussy lips she willed me... no commanded my body to react which it did.

She tortured my clit by varying her tongue touches, her lips and even her teeth. Tugging, licking, nipping me higher and higher as her strong hands held me in position. I could feel her gripping my buttocks, moving my lower half in synchronicity with her mouth. When I came it was like an explosion of pleasure inside me bursting out of my pussy and into her mouth.

When I came down from whatever heavenly cloud she had transported me to I whispered softly, "I want you."

I started by kissing her lips which had just given me so much joy, tasting myself on her flesh as our tongues entwined. I sucked her tongue into my mouth, drawing from it and the last vestiges of my juices before I continued my journey downwards.

I was determined that tonight I would give her something special and running my tongue around each nipple, I suckled like a baby before fastening my teeth gently on her stiff flesh. I was rewarded with a deep moan and her hands caressing my head as I gently squeezed. Working lower I applied all that I learned from the other women I have been with. I felt so satisfied sending her into an orgasm, her moans, and her hands pulling on the bed sheets, all made me feel I was in heaven again.

When she came, I didn't stop, instead, my tongue lashed at her pussy making her moan and writhe, her whimpers like music to my ears as she arched and thrashed. When finally, I relented and allowed her to float back to earth from the heavenly plateau she had transported me to earlier, we hugged and slept in each other arms.

The next day was fun and relaxing on the beach. We swam, talked, had drinks, and it was mid-afternoon when she looked at me,

"Are not you hungry?"

With her hand caressing my thigh. I knew the look,

"Very hungry love."

No more words were said as we walked back to the room. Once inside, I felt her strong arms around me, her lips on my neck and her weight on me as she walked me to the bed.

"God, I wanna fuck you so bad.'

She walked to her bag and pulled her harness, a glint in her eyes that told me she was in an energetic mood "I always travel well-packed", she laughed. There is something so sexy about watching a woman don a strap-on. How she is transformed yet remains the same, feminine yet with a male appendage jutting from her groin like a totem pole of pleasure.

I almost clapped my hands in joy like a schoolgirl getting a present as she settled it in position and mock growled, "Come here."

I slid to the edge of the bed, sitting on the side as she stood there with her hands on her hips waiting. Leaning forward I started to suck the strap on, coating it with my saliva, not that it would need much lubrication as I was soaked.

She leaned forward, placing her strong hands under my armpits and lifted me up and onto the bed before grasping an ankle in each hand. Like a well-practised machine, I splayed my pussy lips with one hand as I grasped the dildo with the other, placing the head at my entrance. Our eyes locked as she sank slowly into me, deeper and deeper, filling me with plastic cock and full of love.

Roxy is a master of the strap-on with such variations that send me wild. She started with a slow steady thrust driving the full length in and out. There was barely a pause when she was fully home before she withdrew until almost leaving. The speed was constant so making my heart almost beat in time with her fucking.

Her heavy hips drove the dildo in and out and then she started to vary the speed. A dozen fast strokes followed by a dozen slow, stopping when she was fully home. As my body started to respond she would fuck me fast until I almost came then slower, allowing me to come down a little. Then repeating the process, she would drive me higher until finally I screamed and clawed her back as I came for the first time of many times that night.

At one point she lifted me from the bed, the strap-on still deep inside as she pulled me on top. I was so uncoordinated by that point that my feeble attempts didn't satisfy her and with ease, she moved until I was again on my back, bent almost double. I could feel the head of the strap-on banging at my cervix making me wince yet moan in pleasure as her relentless fucking continued.

There came a point where I looked up at her and groaned, "You better stop if you want me to be able to stand and walk again."

She laughed as she looked down at me, half of the strap-on still embedded in me.

"Who said I want you to walk, maybe I should keep you like this."

Wrapping my legs around her waist I pulled her close and locked her inside, our mouths mashed together as we lay there content with where we were.

That evening we had a lovely sit down by the beach, holding hands and watching the sunset. We sat in silence as I basked in the glow that comes from being with someone you love. It was one of those beautiful moments I wanted to capture, bottle and keep forever, like the world's finest wine.

Travelling together was a high point in our relationship. We spent three lovely days together, every moment together, which we didn't do before. I spent some nights here and there at her place before, but this was different since it was not interrupted by life obligations, work, or other lovers. She gave me an amazing time, and I felt pretty connected to her. It was hard to go home alone after we returned.

I thought of our time together as I settled home after the trip. Our relationship really grew into a strong connection. The buzzing questions in my head were,

Did I want more growth?

Did I want to move from our current status to a more involved one? Maybe a committed one?

I slept with Jill a couple of times and I know Roxy was sleeping with other women. This was the understanding from the beginning, that we were not exclusive.

Did I want this to change?...and if I do, does she?

Do I want to learn more about myself?

Explore more?

Or do I want to settle in a committed relationship?

Many factors played into that. I wasn't much removed from my marriage, so am I ready?

I was at a relatively new job where I just got my feet wet and started making good progress. At the core, I moved for a higher role and aspired for even more leadership.

Then again, what about Roxy? Does she want any of that?

I decided to just go with the flow, just like I've done with this whole "new era" till now and see how it goes.

"You wanna keep some clothes here, so you could head to work from here in the morning?" Roxy said one evening as I was putting on my clothes to go home.

We had dinner with a few of her friends at her place that evening and I had early morning meetings the day after.

"I wouldn't have been this late if you hadn't wanted to..."I paused and looked at her lying in bed on her side, resting her head on her hand, still naked but for her strap-on on "...have sex".

I giggled as I admired her strong Amazonian body as well as her femininity.

She laughed "And you didn't want to?"

As she stood and walked behind me while I was fixing my clothes in front of her mirror, she kissed my neck and looked into my eyes in the mirror,

"You were so hot tonight, I couldn't wait for the girls to leave,'

Then she kissed me more on the neck and I turned and kissed her,

"I more than wanted it."

"Why don't you spend some days of the week here?" she said as she walked to the bathroom, "I think we should spend more time together."

She sounded pretty serious there and I felt my heart beating a little faster... was she asking me to "semi-move in?".

A lot of thoughts went through my head in the hours and days following that conversation. How I felt about Roxy, how I felt about myself at that point, what does this mean, and many other thoughts. I decided why not, after all I like Roxy and if it works out then great, and if it doesn't then I would've explored another aspect of this lifestyle.

We had plans that weekend for dinner at one of her friends on Saturday, and I was waiting with a couple of carry-ons when she drove to pick me up. She smiled when she saw me, came out and held my hand, rubbed the back of her other hand on my cheek and helped me put the bags in her car.

"I see you decided to spend a few days at my place," she said with a smile, her hand placed on mine as we got in the car,

"I sure did," I smiled back.

I had spent weekends over at her place before, so not much new there for the weekend, but Sunday evening was different. I went back to my routine of preparing my stuff for the week, worked some and had clothes ready for Monday. She was nice and made sure I had what I needed.

We watched TV in bed that night and I must have gone to sleep. When I woke up Monday, she was up already and had coffee ready for me. It felt really nice having that type of relationship back in my life, someone to kiss before leaving for work, something I've not done with my ex-husband for many years. It felt different going back to her place after work and we had a nice evening with dinner then relaxed with drinks in her backyard.

"Are you enjoying this?" She asked as she brushed her foot on my leg.

"I am," I smiled as I sipped from my wine, "very much."

I felt warmth and maybe some romance as my head started going to places. Then she stood up and carried the bottle of wine, and I followed. We had sex many times before, but this one had a little something extra into it, the feelings that I was having, the thought that I was taking another step in the relationship.

I was making moves like I did not before, went down on her first; licked, sucked and fingered her to orgasm. She told me that it felt like I was more liberated and that I was for sure. She went down on me then and I felt my pussy was about to explode to a big orgasm as she masterfully made love to it.

I was lying in her arms afterwards when she teased, "How do you feel about morning sex before work?".

I laughed, "I don't know, I never had it."

She laughed as she replied, "Everything has a first time."

I joked that we better wake up early for that and she smiled, maybe I was reading too much into things, but I felt she may not have liked that comment.

The next day was similar, except that it was a little cool that we didn't sit outside. She was lying in bed when I came out of the bathroom, I said,

"You know, my first meeting is not till 11 tomorrow," and winked at her.

She smiled and we watched some TV, and talked about dinner the next day before she announced,

"Tomorrow you are the chef."

I laughed, "Challenge accepted."

I fell asleep watching TV and when I woke the next morning she was not in bed. I wasn't sure where she was, and then she walked to the kitchen in her running clothes a few minutes later while I was having coffee. She looked sexy with her sweaty T-shirt, her strong arms and legs ripped after running and stretching, her sweat-covered skin shining in the sunlight.

"Morning," I said with my eyes roaming her body as she took off her shoes "Tired after the run?"

"Rather refreshed," she smiled as she walked to me, "slept well babe?"

I could smell her workout scent, "I did"

She held me in her strong arms, lifting my chin as she said with a grin, "Should I jump in the shower?"

"Please don't," I murmured.

I loved her scent, it felt so natural, so real. The thought of 'my partner' coming back from her morning run, wanting to make love to me just as much as I wanted her to, pleased me no end.

"Awww, you want it to be raw," she leaned and kissed me, a long passionate kiss, her hands were touching me everywhere as we kissed our way back to the bedroom, me walking backwards under her power.

"Get the strap-on."

I tore the drawer open where the instrument of pleasure was kept and held the harness open allowing her to step in. As she slipped into it, I could see her muscles rippling and the heady smell of her body was sending me wild with desire.

She stood next to the bed holding both ankles in one hand and pushed my legs back as she thrust her cock into me. I felt the whole thing going in all the way with each thrust as I was fully exposed. Not pure raw sex like Lexy, but rather raw with passion as she thrust into me, each stroke deliberate and precise.

Then parting my legs, she pushed me up onto the bed and climbed on with my ankles in her hands. Putting her cock back inside me she started moving slowly as she brought my feet to her mouth and kissed them. I felt electricity going through my body, from my toes to my head as she sucked on my toes, licked between them, and bit on my ankles with her thrusts coming one after the other.

She murmured, "Oh baby, you are so sexy," which left me with a new horizon.

Her pace quickened as she verbally encouraged me to cum in between sucking each toe with passion as she used her powerful body to propel the plastic shaft into me.

"Cum for me baby...show me how much you love me making love to you."

When I came, I arched off the bed, bent like a bow screaming at the top of my voice, "I love you."

I was so satisfied as I lay motionless as she lay next to me,

"That was hot," I said as I turned to her, brushed my foot on her leg then brought it to her cock "didn't know you liked feet," I teased.

She laughed "Always loved your puffy ankles."

I laughed, "Hey, I don't have puffy ankles."

"Yes you do," she said with a wink.

I felt different at work that day. I felt so good, relaxed, energetic and motivated. Morning sex before work was something I did not have before, so that was one thing, but it was not only the sex that made me feel that way, since I had a good fortune of good sex as of late. It was the growing connection with Roxy, the way things were building between us, me staying at her place and sharing daily routine life as a 'couple'.

"Am I really living with my partner?" I thought to myself as I looked through my office window.

I ran to the grocery store after work and brought what I needed to cook dinner. I also picked out a couple of bottles of wine, a nice Cab and a refreshing Sauvignon Blanc. We had the wine and talked while I was cooking dinner, which felt very natural and warm. Maybe I was hypersensitive at the time, but everything we did together felt like it meant more growth in our relationship.

"Dinner was so good," she said as we lay in bed watching TV with our feet tangled together.

I was at a business dinner the night after, and then Roxy had to finish work on Thursday, so we did not spend as much time together, but that felt like a normal routine life that we shared.

I was putting on my clothes on Friday morning when Roxy woke up,

"Leaving without a goodbye?" she teased with a smile.

"Of course I won't," I smiled as I walked to the bed before leaning to kiss her. The kiss turned into multiple kisses, and I felt her arms around me bringing me closer to her.

"You look so sexy in business attire," she laughed as she unbuttoned my blouse and buried her head in my cleavage.

"I gotta go to work," I giggled.

"I want you now," she said as she pulled me to the bed and put me on my back.

She lifted my skirt up my thighs, brought my panties to the side and started licking my pussy. I could feel her fingers holding the delicate lace away to allow her access to my pussy, her tongue flicking inside as it danced its tango of pleasure, like a hummingbird sipping nectar. As I felt myself get wetter and wetter she suddenly stopped,

"Now I am going to fuck you."

Part of my brain was screaming that my clothes would be ruined yet inside I wanted to give her pleasure by cumming on the strap-on she was fastening around her waist. In the end, my lust for her overcame any thoughts of sensibility and I moved to unzip my skirt to at least save that from wrinkles.

"No," she said with command in her voice, "get on all fours."

I complied quickly and felt her push my skirt up higher until it was scrunched around my waist. She pulled the gusset of my panties to one aide and forced the dildo into me making me moan with pleasure.

As she thrust in and out she muttered, "Do you like being fucked Lady Boss?"

I glanced into the mirror and could see myself in my business suit, my hair wild, my skirt around my waist as a naked Amazonian woman drove her strap-on in and out of me. Her nipples were proud as she moved in powerful strokes and at that moment our eyes locked in the mirror.

She was pulling me back to her using my skirt when she took me doggie, then laid on her back and I straddled her, still almost fully clothed.

"Oh baby, you are riding it so well," she murmured which motivated me to ride even more energetically. I felt her bending her knees underneath me and I knew she was about to take over. Then she started thrusting up and I felt her pushing all the way in, holding me then pulling out before she pushed in again. Then Roxy did the move that I always loved, she flipped me on back with her cock still buried inside me and went on thrusting while laying on top of me. I was holding into her strong arms, wrapped my legs around her powerful body. I was holding her so hard like I did not want to let go of this, maybe forever.
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