by Jessica Sin
She continued with her taunting, saying, “You’re awful. How could you allow your poor secretary to jerk you off like this after fantasizing about her for so long?”
“I’m about to cum…” I panted.
She quickly leaned forward from where she sat and took the head of my cock inside her mouth and began sucking. It felt incredible. The sight of her lips around me and her cheeks caving in from her vacuum like suction was surreal. She kept stroking furiously which was followed by loads of my cum shooting to the back of her throat, which she willing swallowed without any hesitations. She kept me inside her mouth until every last drop of my sperm had been devoured, and I became flaccid with her lips still around me.
“You taste good,” she said, licking her lips clean. “Now if you’ll excuse me, I need to wash up so I can start preparing your files.”
She gave the head of my cock one final kiss before putting her top back on and leaving.
***
This became our little secret. Every so often, she would let me fondle and suck on her breasts, and afterwards she would do the same to my cock. If she was in the right mood, she would even talk nasty to me which we both found to be so arousing.
The one thing that was off limits, however, was her panties coming off. I had asked her a few times if I could return the favor and make her cum and she would politely say no. She considered it to be too personal and that her vagina was only for her husband. I didn’t want to bother her about it since I didn’t want to jeopardize what we had, so I never brought it up again.
***A SPECIAL SURPRISE***
It had been three months since Ellen had given birth, and a month and a half since our working relationship turned sexual. She had also recently returned to work full time and had hired a baby sitter from down the street so that I could find more time for some important clients.
One day, I arrived to find a note on my desk which read: “Do whatever you want this morning, but be back in your office this afternoon. I’ll be back early to give you a special surprise.”
A few hours had passed and she came in right when she said she would, dressed in her business suit with her make-up and hair done up extra nicely. What especially made her sexy was that she wore her normal tightly fitted business attire, but her breasts and hips were still larger than usual, which enhanced her curves even more.
“You wanted to see me?” I asked as I greeted her at the door.
She put her things down and held my hands, “Yes, I have something for you- something special. In 5 minutes, I want you to come up the stairs to the boardroom, not a second earlier.”
She kissed me on the check before walking away.
***
The time came and I nervously made my way up the stairs. Seeing her earlier had made me nervous. Her describing this as ‘special’ must have meant something because she never referred to anything we had done previously in that way. Whatever it was, I couldn’t wait to find out.
My jaw nearly hit the floor as I reached the doorway of the boardroom. Ellen was completely nude with her arm leaning against the lecturn. She stood there looking bold and proud of her post-pregnancy body as she modeled herself to me for the very first time.
My eyes took in as much of her as I possibly could, examining the thickness of her bare hips and thighs. Her pubic hairs were neatly trimmed, and her large sagging breasts were able to grab my attention the same way they always have. It looked as though she re-applied her make-up and fixed her hair by tying it up in a fancy pony tail.
“Like what you see?” she asked, exuding a newfound confidence.
“Oh god, you have no idea how I feel about you right now. You are absolutely perfect,” I told her.
“Thank you, your compliments always mean a lot to me,” she said. “I have something to confess to you. Come her, have a seat next to me first.”
I did as she asked, walking over to where we both sat next to each other.
She continued, “I don’t think you know how much I’ve enjoyed what we’ve been doing lately. I even find myself masturbating in the bathroom stall at the office, wishing we could do things together at that moment. But what’s made this even more thrilling is that my husband knows about all of this. I’ve told him early on and he loves hearing about it while we have sex. He makes me tell him every single detail about what we do, and I love telling him about it.”
“Really? I would have thought he would have freaked out if he found out about this.”
“I thought the same. I dropped little hints for him to see if he was receptive to any this, and as it turns out, it drove him wild and it was the perfect thing we needed to spice up our sex life after being married for so long. But back to the point, you’ll be leaving soon and we thought we’d give you a going away present you’d never forget. It’s something all of us would enjoy in one way or another. How would you feel about having sex right here, right now, with me?”
I nearly gasped at Ellen’s offer. “Did you even need to ask? Of course I would! God, I never thought it would ever come to this. This is the most erotic thing I could imagine.”
“You’re right, this whole thing is so erotic, so taboo. I would be horrified if anyone ever found out about this. I wouldn’t be able to show my face anywhere because of how indecent and immoral we’ve been since the day I lifted my shirt for you. But that’s the appeal. What we do sexually stays within these walls.”
“Of course, I understand completely. Believe me, I wouldn’t want anyone knowing about this either. But I’m so happy that we get to do this together.”
She stood up right in front of me and said, “Well, to make things clear, we won’t be having sex in the traditional sense. That’s still something only my husband can have.”
She then turned around to reveal her large round voluptuous rear end to me, and wiggled it so that it would shake a little. “Have you ever had anal sex with a woman before?”
“Once,” I replied.
“Good, now get up and I’ll help you undress.”
The first thing that happened when I stood was her reaching underneath my t shirt and pulling it over my head. That was followed by her yanking down my shorts and underwear, leaving both of us completely nude.
“There’s lubrication on the counter over there, I hope you use a lot of it for my sake,” she joked.
I quickly grabbed her around her waist, pulled her towards me, and kissed her full on the mouth for the very first time. I pressed my lips as hard as I could against hers. And she responded by doing the same with our tongues eventually meeting in this sensual and erotic moment between us.
“I’ve wanted to do that for a while now,” I told her.
She smiled, “Now that we’ve gotten that out of the way, let’s get started.”
I turned to grab the small container of lubrication from the counter, and Ellen got on all fours on the bed. When I got behind her I was treated to the sexually explicit sight of her little brown anus, her thick brown labia, and her sagging breasts hanging downwards, nearly touching the bed. I was able to get a clear look at the pink insides of her vagina from this position. It was glistening with moisture and there was no denying how aroused she had to have been at that very moment. As for her anus, it looked incredibly tight to the point where I wondered if I could even get my finger inside, let alone my cock. But I was up to the task.
I poured a large helping of lube onto two of my fingers and pressed it against the delicate opening of my secretary’s rear end. I took a moment to feel the softness of her anus before giving a gentle push to get my fingers inside of her. She moaned the moment I entered, and moaned some more as I moved my fingers around to coat the tight walls of her rectum with the lubrication. And judging by how much more wet her vagina had become, we were both clearly enjoying my playing with her ass.
She was ready at that point. Her anus and rectum were opened and lubed enough for me to penetrate her, and so I pressed the head of my cock against her most intimate of areas and gave
a small thrust. She gasped as soon as the head of my cock entered her body. Her hands squeezed the blanket tightly, and her legs and feet became stiff. With the next few inches, her gasps and whimpers became louder and she clenched her hands even tighter as I was stretched her rectum further. And as I pushed the final few inches in, I was able to witness the almost unbelievable view of my cock being completely devoured Ellen’s once tiny hole.
“Fuck me…I want you to fuck me now,” she pleaded, with the sounds of lust and desperation in her voice.
I gave her what she wanted, what we both wanted, the best that I could. It went slow at first since the tightness of her anus and rectum felt like the grip of a hand. But as she loosened up, I was able to fuck her harder, filling the room with her loud whimpering and the sound of my cock slurping in and out of her well lubricated asshole.
I had never felt anything so pleasurable in my life as shehad become completely submissive to me. She was completely at my mercy, and I loved that. As I continued fucking her, I reached down to squeeze one of her milk filled breasts before going down even further to rub her soaking wet vagina, causing her to cry out loud. I loved the way her big clitoris and labia felt against my fingers, and I loved that she was on the brink of a powerful orgasm that I was able to give her.
A sudden stream of fluids rushed through my fingers that were in her vagina. Her back became arched as she orgasmed and screamed at the top of her lungs. She was completely uninhibited with her pleasure knowing that we were home alone, as her arms and head thrashed on the bed, being as loud as she wanted to be because only her son could hear. I grabbed tightly onto her hip with my other hand and shot load after load of my cum deep inside her rectum, filling her up with what probably was the largest amount of sperm I had ever produced.
We both collapsed onto the bed, with me on top of her. I then planted kisses on her shoulder as she was catching her breath.
“God you were amazing,” she said, still panting hard. “That was the best anal experience I’ve ever had.”
She turned her body and gave me a deep kiss on the mouth for the second time today. This time, it was more sexually charged after the experience we had just shared with each other, with our tongue’s slobbering all over each others lips.
“Tell me we’ll do this again soon…” I said, in between kisses.
“Of course we will…”
“And after I come back from the conference?”
She smiled, “Who knows, maybe by the time you come back, I’ll have permission for you to cum inside my womb.”
The End
A Summer With My Nanny
My nanny Zara has always been very liberal when it comes to sex.
It’s just how she was raised, and how she eventually raised me. Talking about sex and adult matters was never a taboo issue in our household. In fact, she would even go out of her way to have these discussions with me so that I would know what to expect growing up. My parents on the other hand, seemed to be a little more modest on that issue, but they didn’t argue about it with Zara either.
But the one thing my parents both whole-heartedly agreed on was their love for the outdoors. They loved being in nature whenever they had free time. My father would sometimes even take us on long trips during the holidays to where the sun was warm and the air was fresh. He’s made a career as an author, so those vacations also allowed him to work on whatever book he was currently writing.
This summer, while I was still on break from college, my parents decided that we would all go to a house by the lake which he rented for two week. And it would eventually become a summer I would never forget…
Summer With Zara
The sun had just come up in the morning on the second day of the trip. We had all gone to bed early the night before from the long car ride we had, so there was no problem for me being wide awake at 7 am.
I took in the view of the lake through my room’s window. The sun light was reflecting off the water and everything felt perfect.
But then I saw something which would change the entire course of this trip for me. I saw Zara completely naked as she was coming out of the lake. She had gone for an early morning swim without a single piece of clothing on and was walking over to her towel to dry herself. She ran the towel through her long dark wet hair. Then she used the towel to dry her tanned body, along with her large breasts with its brown nipples. Her body was slightly curvaceous with a thick dark bush.
When she was done drying herself, she casually hung her towel on a nearby clothing line and proceeded to do her usual morning stretches after her exercise. I was then treated to the wonderfully erotic sight of her twisting and turning her body every which way to loosen up her muscles for the day. My favorite part was when she stood straight up and then bent down to touch her toes, and I was able to see her large breasts hang downwards.
Once she was finished with her early morning routine, she took her time getting dressed. I watched as she put on her white colored bra and panties, completely unaware that she was being voyeured, followed by a casual sun dress. And after she got dressed, she came back inside the house.
I couldn’t believe that I had finally seen Zara naked for the first time in my life. It had been a long forgotten fantasy of mine, starting from when she used to lecture me about how natural sex is and how it’s a part of life, and of course how beautiful I thought she was. I even used to masturbate regularly thinking about her. But as open as she was about discussing sex, I was never able to see her since she would always keep her door closed whenever she was undressed.
I no longer cared about the lake or anything else we had planned for that vacation. All I could think about was when I was going to see her body again.
***A FATEFUL AFTERNOON***
We were all relaxing around the house after spending the day swimming, eating, and just having fun in the summer weather by the lake. My dad was in his room, busy with his new book, and Mom was busy doing something in the kitchen. That’s when my nanny announced that she would be going outside to lounge in the sun for a little while longer. And after letting everyone know that she would be back in a few moments, she grabbed a towel and headed out the door.
My heart began racing at all the different possibilities. Zara was obviously going to be naked outside again and I was just a short distance away. It didn’t take long for me to make the decision to go out and try to spy on her for the second time that day.
***
I went outside in the direction she headed in after seeing which way she left the house. It wasn’t hard to find her as she was just settling in to her spot on a beach blanket right in front of the lake. She was only topless this time and had a bikini bottom on. Her arms were spread apart and she was truly at ease, letting her body soak up the warm rays of the sun.
It was hard not to just walk over there as quietly as I could because I knew I would get caught if I did. But I couldn’t resist not taking a few steps in her direction so that I could get a better look. And as I made my way closer to where my nanny was sun bathing, I was able to get a better look at her breasts spread across her chest while she laid back.
She suddenly turned her head in my direction and grabbed the towel to wrap around her body. She had just caught me and I desperately tried my best to hide behind a tree.
“Is that you?” she asked. “I know you’re there. What are you doing here?”
She came towards me with a curious look on her face wondering why I followed her. And of course I felt utterly humiliated in the process.
“I just…wanted to see what you were doing,” I told her.
“I already told you in the house what I would be doing out here” she replied with a stern look on her face. “You were spying on me, weren’t you? Why would you do something like that?”
“Do we really need this conversation?” I asked back.
She nodded.
“Fine,” I sighed. “This is so embarrassing but…I saw you swimming outside early this morning, and I
just wanted to see you again. It’s all I’ve thought about the whole day. I hope you aren’t mad.”
A smile suddenly appeared on her face as if she wanted to laugh at me. She then pulled the towel tied around her chest and opened it, revealing her bare breasts to me. Her nipples were large and brown, and stood out for nearly half an inch. Her areolas were also fairly wide and were a lighter shade of brown. Her breasts were also fairly large, c cups, and they sagged enough to show that she was a middle aged woman. Seeing them from far away did no justice as to how big they were.
She then waved her towel around and did a playful dance as if to tease me by jiggling her breasts.
“You see, they’re just boobs. It’s nothing for either of us to be embarrassed about.”
