I decided to take my personal assistant, Dakota, with me to a conference because I thought she would enjoy a long weekend stay in a fancy hotel, especially since she was getting married soon. I wanted to do something nice for her, you know? I’m a 49-year-old businesswoman, married, and Dakota is a lovely 24-year-old who has been working for me for about three years. [Photo from another Dakota].
She’s a highly competent young woman, but she’s also a bit of a different person.She’s quite attractive, but she prefers to dress modestly, almost old-fashioned, and her shapeless dresses make it difficult to tell if she has a slender and beautiful figure.I presume she does, though.She also always comes across as very serious. We left on Thursday and arrived at our destination just after 7. At the reception, we learned that something had gone wrong with our booking.A room with two beds had been reserved instead of two rooms.Unfortunately, due to the crowds around the conference, there was nothing available, so I asked Dakota if she minded if we had to share a room.
With a big smile, she said she didn’t care. I was surprised by her eagerness, as this wasn’t something she usually cared about.Our room was incredibly spacious with a lovely view of the surrounding hills and forests.We unpacked our bags, had a nice chat, and discussed the congress that was about to start.Before we ate, I decided to take a quick shower.Stepping out of the bathroom, dressed only in a bath towel, I looked for a nice set of lingerie. I dropped the towel, grabbed my thong, and began to put it on.I noticed that Dakota couldn’t take an eye off me.By the looks of it, my breasts were the center of her attention, or was I just kidding?I mean, why would a woman soon to be married be interested in an older woman’s body?I pulled on the matching bra and put on the dress I had picked out for tonight.
Dakota also dove into the shower, and I was amazed at how old-fashioned her lingerie was: spacious underpants that wouldn’t have been out of place for my mother, and a bra that looked like it was supposed to hold her breasts—which were very nice—captive.We went to the restaurant and ordered something to eat and a bottle of white wine. Dakota said she didn’t often drink wine, in fact no alcohol, but going forward, as a special treat with dinner then tonight. To my surprise, she soon had half the bottle behind her and became quite talkative, which was nothing to her. I also noticed that she often glanced at my breasts. I had put on a bra, but the dress was more of a sundress, so my nipples were visible through the thin fabric.
I tried to bring the conversation to her upcoming wedding, but she seemed rather reserved about it. Besides the fact that everything was almost arranged, she didn’t say anything else about it, including the groom. When we finished eating, I said I wanted to go to our room because I had to be at the first reading early tomorrow morning, and I wanted to get some sleep. I hadn’t brought any pajamas because I was expecting to have my own room. I always sleep naked, and I also masturbate very regularly before slipping deliciously into dreamland afterwards. It’s just part of my morning routine, and it helps me unwind and let go of all the worries and stresses from the day. Besides, it’s just so enjoyable.I thought to myself,
“Oh, well, I just sleep naked. Why should I do anything else now? She’ll just look the other way.”I didn’t see the problem, so I took off all my clothes and walked naked to the bathroom. I felt Dakota’s eyes on my body, especially on my slightly heaving breasts, and her gaze made me feel very sexy. I walked to the bathroom at my leisure and twisted my hips extra sensually.After I finished there, I walked to my bed and slipped naked under the fresh sheets. The smooth linen felt delicious against my skin, and the cool fabric made my nipples tighten and stick up stiff. To my surprise, Dakota also took off all her clothes and for a moment she seemed hesitant to stand beside her bed in her nakie, as if she wanted me to look at her naked body.She had a beautiful body, her skin was very white, flawless, with her dark brown nipples standing out brightly.The nipples stood proud, slightly protruding on her full apple-shaped breasts. Her pubic hair, black as her hair, was as contrasting as her nipples against her white skin.I thought to myself, “Her fiancé is a lucky guy.”When she returned from the bathroom, to my disappointment, she put on a solid long nightshirt.What a sin to hide such a beautiful body.
She wanted to get into her bed, but hesitated.”Do you mind if I have another drink from the minibar?” “Of course, you may,” I replied, “take whatever you feel like, just give me another glass of red wine.”She walked over to the minibar and took out two bottles of wine. She poured the wine into glasses and came over to me with them.She reached for one, and when I took it, the sheets slid down, and my breasts were completely exposed.Her gaze made my nipples tingle. “Hmm, I wonder if this is a bit unusual,” I thought to myself, “I get turned on by my assistant’s attention… Keep an eye on this, ma’am!”As Dakota sipped her glass, she walked over to her bed and lay down on the sheets. She drank her glass in one big gulp and placed it on her nightstand.We were both quiet for a moment, and then she looked at me.”I’m not sure if I should get married,” she said. “Why?” I asked, surprised. She blushed, her cheeks bright red.
“My husband… well, we’ve never had sex. He never touches me there,” she said, looking at her breasts and crotch.”He doesn’t want me to dress sexy. It’s not good to do that before marriage.””Oh God,” I thought, “I thought there was no such thing anymore.” “Um, yes, some religious people think that’s how it should be,” I offered.”I know that,” she agreed, her voice tinged with hesitation.”But if we cuddle at all or something, I never feel him get an erection.I’m afraid he doesn’t like me at all, doesn’t find me attractive.I get so frustrated,” she sighed, her voice a soft moan.”Then you must masturbate a lot,” I joked, trying to keep it lighthearted. “No,” she continued, her voice serious.
“That’s also not okay according to him. I’ve never had an orgasm, for crying out loud. I had another boyfriend before this, we had sex too, but never cum with him either.”She paused for a moment, her face a picture of confusion.
“Maybe there is something wrong with me,” she said, her voice cracking with emotion.Her candid confession surprised me, because this was so not Dakota. Could the alcohol have loosened her tongue? Suddenly, I realized I had placed my hand under the sheets, between my thighs, and was gently caressing my pussy. It felt so moist. I withdrew my hand, a little startled, and asked, “What was I doing?” Dakota looked at me, helpless, and suddenly burst into sobs.Oh, how sad and vulnerable she looked. I gently slid the sheets off my naked body, placed my glass on the nightstand, and walked over to her. I gave her a hug, trying to comfort her, and she cried out almost soundlessly on my shoulder.
I felt her tears running down my back.She took a deep breath and tried to sob away her tears.”I’m so glad I can talk to you about it.” Her soft fingers began to caress my back, and my skin trembled with pleasure.With tearful eyes, she looked up at me and tried to breathe in and out quietly.”Will you teach me… will you teach me to cum? Please, yes?”My own emotions and feelings tumbled over each other. Sitting there naked, a beautiful young woman in my arms, my heart was beating like wildfire, my nipples were on fire, rock hard, and I felt a strong sexual attraction between us. “The best way to cum is to get to know your own body. Masturbate and discover, try out, feel what you find delicious.”
“Don’t you want to do that?” she interrupted me, “make me cum… now… please.” She sat up straight and fumbled for the hem of her nightshirt, grabbed it, wiggled her bottom off the bed for a moment, and pulled it over her head.Her skin was so silky and pure, her full breasts exuded sexual desire.As my eyes slid over her handsome, delicate body, she opened her thighs slightly, and I got to see her labia between the full bunch of dark pubic hair. “Touch me,” she begged, taking my hand and guiding it to her tight belly.
“Please do it, make me cum.”Her belly felt warm, and even though I knew better, my fingers followed an invisible path down toward her pussy.Dakota moaned as my fingers found her pubic hair and made their way down, following the curls that soaked her hidden most intimate spot. I touched her labia, which eagerly opened up, revealing the moisture beneath. “Don’t stop, keep going,” she purred.I slipped a finger between them, and her pussy felt like liquid velvet.
I moved it slowly in and out of her wet pussy, trying to give her that pleasurable feeling she craved, what she needed.I crawled onto the bed, pushed her thighs further apart, and sat between them. I could see how eager she was to feel my finger slide in, so I took a step back to let her enjoy the moment. But then, I gently pushed it back in, stopping only when my knuckles touched her lips.I could feel her arousal, and I could see her clit, clearly responding to my touch. I took my finger out and opened her lips, exposing her clit. It was dark pink, so stiff, and almost as big as the nail on my little finger.
“Don’t stop, please, help me…”I put two fingers on each side of her labia, all the way at the tip, and forced them open completely.They turned even lighter pink, and the cap above the clit slid up, exposing her pink pea. I lowered my head between her thighs, smelling her bloated pussy. I lowered myself closer, and my tongue ran over her hard little bud.Dakota let out a scream.”Oh my God, oh my God!”I inserted two fingers into her pussy, the ridged walls of her vagina gasping hungrily…at the same time I pressed my mouth to her clit and sucked it gently between my lips.
Dakota was very aroused, horny, and she moaned and groaned and twisted her hips against my face. Her hands slid over her belly, but moved higher and higher, toward her breasts.Soon they were kneading them, and when they found her stiff nipples, she grabbed them between thumb and forefinger and pulled on them hard, stretching the dark nipples.Her nipple hilts became little bumps on her quivering breasts.She pressed her lower belly up, against my sucking mouth.
She was starting to lose control, which was a good sign. I opened my mouth and started licking her clit. Her thighs tightened, and I gently placed my teeth on her hard bud.Dakota let out another scream, and her lower belly came loose from the bed.She said, ‘Oh God, what is happening to me now? What is this? Help me, please, help me.’ I gently inserted my fingers into her, which were already wet and moving around, and sucked on her clit.Her fingers pressed their nails into the flesh of her breasts, and her cunt clamped down on my fingers.She made a whimpering sound, and for the first time in her life, Dakota came. Her body trembled and quivered, and I gently let her clit slide out from between my lips. I watched as her body bucked and her breasts seemed to take on a life of their own.I had my two fingers inserted deep into her pussy, and I felt her pussy muscles clench around them and release them again.
And a steady stream of cum welled up from her spasming vagina, and a sopping sound filled the bedroom.”Hold me, hold me,” she whispered. I snuggled up next to her, our breasts nestling against each other, and felt her nipples pressing against my breasts.Her hands gently guided me closer to her, and our fingers found themselves intertwined in her intimate warmth. I could feel her body responding with delight to my touch, and she gently placed one leg over mine, allowing me to continue exploring her.I could feel her arousal, and I knew that if I continued to tease her, she would be on the verge of another intense orgasm. I stroked and caressed her pussy, and soon she started moaning, and I felt her honey flow over my hand as she climaxed once more.
“I love you,” she whispered.Her mouth sought my breasts and nipples, and she took turns sucking them into her mouth.I moaned, enjoying the sensation, and my own pussy wanted more too. “I love you,” she said again. Slowly, her sucking mouth came to rest, and all her body relaxed.Her face lay on my breasts, and less than a minute later, she was asleep.I pulled my fingers from her pussy and placed them on my lips, and I licked up her sweet, salty taste, my assistant…I carefully crawled off her bed, covered her naked body, and got into my own bed. I lay on my back, spread my thighs, and ran the same fingers that had just been in her pussy into mine. I gently and deeply fingered myself, and with my teeth together, I came groaning, and my honey mixed with the remains of hers on my fingers.The next morning, I woke up early.
Dakota was still fast asleep, and she didn’t notice that I went to the bathroom to get ready for the lecture. She was still asleep when I left the room.The lectures and networking went really well, and before dinner, I made my way back to our room.I pushed open the door, and there she was, naked as a jaybird, hands on her breasts and nipples, wearing one of my thongs. She looked at me, embarrassed, and her cheeks colored a little. “Oh, hello, um, I have a thong of yours,” she said, her cheeks still a little pink. “Oh, that doesn’t matter. What did you do today?”
She blushed and replied, “I, um… I had a lot of orgasms. Really a lot! It’s working out really well now. Oh, it feels so good, delicious!”I couldn’t help but laugh.Dakota had become a completely different woman in a day. She felt so much more at ease, as if a heavy burden had fallen off her shoulders.She continued, “By the way, I’ve made a decision.I’m going to tell my fiancé to fuck me immediately when we see each other again.If not, the whole wedding is off and he’s on his own.Done. If he’s not up for it, well, I’ll have some extra cash to explore other options.
Or, I might just go on a fun trip around the world instead of getting married.””That sounds lovely. How about we head out and grab some new clothes and lingerie for you? I’ll get mine later,” I said with a playful smile. “Then you’ll get that from me as a gift for your new life, whatever path you take later.”She stood up and came over to me, hugging me. Then she asked, smiling broadly, “Do I have time to cum one more time before we go?””Okay, whatever you want. Then I’ll jump in the shower first and you go ahead and do what you can’t resist.” I threw off my clothes, hopped onto the bed, and enjoyed a refreshing shower. Then I walked back into the room, where Dakota was sitting naked on the bed.Just then, there was a knock on the door.
“Oh, that will be for me,” Dakota said, and she walked to the door.I was amazed at the total turnaround this girl had made and watched as she opened the door. A young man from room service entered the room, carrying a bottle of champagne in a cooler and two glasses. But when he caught sight of us two naked women, he suddenly stopped, looking a bit overwhelmed. I think he was around 20 years old. I sat down in the chair next to my bed, pulling a sweater over my head, but Dakota took charge.
“Just put the champagne over there on that little table. Could you open the bottle and pour two glasses?She remained standing there, the young man unable to help but look at her naked breasts and all her other treasures.The rascal half leaned against the open door, putting one leg slightly at right angles to the other so that her hairy pussy was also clearly visible.Her dark nipples were rock hard and stood up proudly.I could tell by the blush on her cheeks that the situation excited her.
With a bit of shakiness in his hands, the young man popped open the bottle, and champagne foamed up and filled the glasses. It looked quite romantic, too. “Thank you,” Dakota said with a big smile, pressing a bank bill into the confused young man’s hand. She held the door open a bit more, and if you asked me, she even held her thighs open, because even I could see her swollen labia. He stepped out of the door, his gaze lingering on the naked woman. He kept looking at her until she closed the door in front of him, and then she burst out laughing.
“You naughty tease,” I said, laughing along with her. “Oh God, that was funny,” she laughed.
“Oh yes, the Champagne is on me. To thank you for everything… my first orgasm and because you’re the best boss in the world.”She grabbed the glasses, handed me one, and we toasted, to each other and the pleasure.We emptied the glass and filled it again with bubbles.”I feel so horny,” she continued, “but if I don’t get a real cock soon, I’ll explode. I want to experience that feeling of a hot rod deep inside my body again. Or even if only a fake one.You don’t happen to have a dildo with you?I burst out laughing.”No, but … I do have two vibrators with me.Would you like to try those?”Her eyes grew wide and surprised she looked at me.”Really?””In the side pocket of my suitcase.”
Without hesitation, she walked over to my suitcase, and I caught a glimpse of her pussy as she bent down to unzip the side compartment.”Oh my God,” she exclaimed when she saw what I had in there, “that’s not true!”She pulled the two vibrators out of my suitcase and held them up.Her eyes flicked from one to the other. “This one,” she said, pointing to the smaller one, “is a nice surprise. But that one… wow! That’s a whole other level! I bet that one won’t fit in your…” I couldn’t help but laugh. “Well, sometimes you just want some pleasure, and sometimes you’re so horny… so naughty… and then you want something special.””And I can use them?””Absolutely.” “I’d love to have you watch me when I use it.””Of course, no problem,” I replied.She returned the largest one to my suitcase and walked over to the bed. She lay down on her back and spread her thighs wide. She placed the vibrator between her legs and gently rubbed her labia with it.”The on button is on the bottom.
A moment later, the familiar buzzing sounded in our room, and Dakota moaned through the stimulation her pussy was undergoing.”Um, actually, I don’t dare… I’ve never done this before… and it’s been so long since there…” she moaned, as her hand sent the vibrator through her slit, but didn’t push it in yet.”Just do it,” Dakota pointed the tip of the vibrator at her wet opening, but still hesitated. She closed her eyes and took a deep breath as she pushed through. The tip parted her lips and slid inside, and she shuddered in pleasure. Her breasts shook a little from it, and she pressed on.Deeper and deeper the toy disappeared into her pussy, and with a final thrust, the last inch disappeared into her secret cave.I saw tears come to her eyes. Surely this girl had missed a lot with her boyfriend…
With quiet, sensual movements, she began to pleasure herself, the vibrator slipping deep inside and out of her pussy. She mumbled all kinds of things, but I don’t think she was talking to me. ‘Oh, God, fuck, fuck… oh, yes, fuck my pussy, take me… ohhh…’ The hand holding the vibrator moved faster and faster, back and forth, while the other hand gently rubbed her lower abdomen, just above her pubic hair. She was so lost in her own pleasure, her breasts looked bigger, her nipples were stiff and swollen. “Oh… oh… I’m about to come… I’m coming…”I put my hand between my thighs and started fingering myself. It was so exciting to see this young woman so lost in pleasure.Her body tensed, and she lifted her hips up off the bed.
The vibrator was deep in her pussy; I could just see the tip, and her pussy clung to it.With her pelvis high above the bed, Dakota came.The words that flowed from her sensual mouth were uninhibited. Wave after wave of orgasm engulfed her trembling body. Her orgasms were so intense, they even pushed out the vibrator, which fell onto the bed, leaving her with only her fingers to use on her soaking wet pussy.I came too, seeing the pleasure my assistant was undergoing and her sheer, unprecedented eagerness to experience it was so arousing…My fingers were wet and slippery with my horniness.Slowly, the woman on the bed came back to herself and she lowered back down, relaxed, her eyes wet from her tears. “Oh my God, that was so delicious!” she whispered, her voice a soft moan.I crawled next to her on the bed, embracing her.
Our breasts and lower bellies were pressed tightly together.After a while, I had no idea how long we had been lying like this. A mischievous look appeared in her eyes.”Now it’s your turn!” “Huh, my turn?””I want to see how you do it… with that giant thing over there,” she said, pointing to my suitcase.”I want to see that thing in your pussy!”I was ready for more, but I was also kind of sad to have lost the young man from room service. Still, my vibrator was a good surrogate, especially at this time, so I scrambled upright and pulled it out of my suitcase. I climbed onto my back on the bed, nestled a pillow under my head, and spread my thighs.Dakota crawled to the foot of the bed, her gaze fixed intently on my pussy, wet, swollen, and ready to embrace that big rod.Even before I pressed it against my slit, I felt encouraged.”Put it in, put it in,” she said, her voice like the excited cry of a child on Christmas Eve. I pressed the head between my labia, relaxed for a moment, and then gently pushed it through.
The first time was always a bit of a struggle, my vagina getting used to the size of the intruder, but soon he was about ten inches inside me.I grinned, from pleasure and a bit of discomfort, but I knew that would only be short-lived. “Oh, it’s so sexy to see, but also a little rude,” Dakota said. “Your cunt is so stretched open. Wow. Can it go any deeper?”I gave in to her excited wish and pushed the vibrator a little deeper into my body.The head seemed to find its way into my womb.I felt so full, taken to the extreme.I shivered, feeling heavenly and diabolical at the same time. I found the button to turn on the vibrations and pressed it to position 1. That was all I needed. I held the vibrator deep inside me, not moving it, and let the battery-powered vibrations come to me, enjoying every moment. I also enjoyed the curious look on Dakota’s face, with the red blushes on her cheeks. I knew this was not going to last long, though.
My spectator and the rubber rod in my pussy would bring me to a splashing climax in no time.I looked for the button again and turned it up two positions.The stronger vibrations drove me to the edge. I didn’t even have to fuck myself with the thick rod; just its presence and the small but oh so noticeable vibrations did the job. I surrendered to the waves of pleasure that enveloped my body, and soon, I found myself trembling and moaning on the bed. My pussy, overwhelmed by the intensity of sensation, could no longer take it. I carefully extracted the vibrator from my opening, and Dakota, mesmerized, said, “Oh my God, just look at it!” as she admired the sight of my arousal. “Your cunt is just open…
She gently placed her fingers on my wet lips, and because of my momentary extreme sensitivity, I involuntarily moved my hips.It was like getting a power surge, being struck by lightning… well, not that, that would probably be fatal.Her fingers were picking at my labia, pulling them apart, exposing me, exposing my throbbing clit…’Oww, your clit is huge. I bet it’s three times bigger than mine…’ She lowered her head between my thighs, and I let out a quiet moan as her mouth closed over my clit, sucking it between her lips like a baby sucking on a breast.It felt like I was cumming again, which was probably true, because my body seemed to be electrified, and my pussy spewed another wave of pleasure over Dakota’s chin.
For a moment, her head came up, and her eyes glistened in the light as she looked at me with a wide smile. “That shopping can be done tomorrow, too. Seeing how you’ve cum now, this boyfriend I have to try out for myself. Never too late to discover something new.”Her mouth moved toward my clit again. “No, no, stop, not anymore,” I moaned, but she didn’t listen. I surrendered once more, and that shopping could indeed wait until the next day.
