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Boss/Subordinate...with a twist  

iwant2squirt2 52F
72 posts
9/17/2011 7:58 am
Boss/Subordinate...with a twist


My boss and I were sharing a hotel room at a conference. Because they made us share, the company had a least graciously given us a suite with a bedroom and living area with pull out couch and a large Jacuzzi tub.

After a long day of meetings, we went out to eat before heading back. We get along really well and often shared stories of family struggles, this night was no different. After a few drinks, she confided in me about the struggles she was having and her impending divorce. I bemoaned my single-ness and inability to find a man who fulfills my needs. We sat and chatted over a few more drinks before deciding to take a bottle of wine back to the room.

As we sat and chatted easily in the room, I made up the pull out sofa, figuring that’d be where I was relegated to sleep being the subordinate. Our conversation slowly turned to sexual preferences. We joked about inadequate men, masturbation and general lack of partners. We realized how late it got and were starting to think of sleep. “Hey, let me give you a massage before bed.” I said, “I’m really good and it will relax you so you sleep well.” She hesitated, I could see she was uncomfortable. “Hey,” I said, “we can do it just like at a spa, I’ll go in the other room, you undress as much as your comfortable and lay under the sheet.” She agreed and I stepped out. While in the bathroom, I rummaged through my toiletries and found some baby oil. Not the best option, I thought, but it’ll do. I waited a few minutes to give her ample time and then went back out.

I chuckled to myself when I saw her bra straps under the sheet, she was more uptight than I even realized. I silently pulled the sheet back until she was uncovered just to the crest of her ass (and her panty waistband). I boldly undid her bra, and gently pulled it away from her skin, giving me a “blank slate”. I put the oil on my hands and rubbed them together then pressed them to her skin. I started in the middle of her back and pressed my hands outward, moving up and down her back. I moved up to her shoulders and moved my hand under her straps to easily massage her shoulders and sides of her neck. I heard her sigh and felt like perhaps I was actually starting to be helpful. I massaged her back using a variety of techniques: gentle caress, deep pressure, kneading, using my fingertips to manipulate her flesh. Then I covered up her back. She started to move and I softly said, “not done”.

I lifted the sheet from the bottom, exposing her legs and panty-clad buttocks. I felt her tense up. “Relax” I said softly, “this will feel great”. I moved to the bottom of the bed and re-oiled my hands. I started at her feet and slowly moved up her right leg, using the same techniques as I had on her back. The further up her leg I traveled, the harder her breathing got. I noticed when I was about mid-thigh that she had grown a little wet spot in her panties. I smiled, feeling my own area start to tingle with the realization I was turning her on. Almost immediately my mission changed from trying to relax a friend to thinking about getting my boss to orgasm. I moved further up her right leg, using slow, deliberate motions now. When I got to the bottom of her ass cheek, I let my hands move inside her panty leg. I caressed her ass cheek, kneading it with both hands. She wiggled a little. “Hold still” I told her, “really this will make you feel better”. I noticed her wetness growing. I pulled my hands down over her ass making sure to brush over her panty covered pussy and then pulled my hands hard down her right leg…a great massage move. Then I set out on her left leg doing the same thing. I knew I was teasing her horribly and when I got back up to her ass on the left side, I was aware that her hips were pumping ever so slightly.

After I finished with her legs, I told her to roll over. To my delight, she complied without question. Once she was on her back, I again removed the sheet from her body…this time completely. I went to her side and slowly lifted her bra off of her. She kept her eyes closed. I took a deep breath and went in. I took my tongue and started at the base of her large, slightly sagging breasts. Slowly I moved in circles around the base, massaging her flesh with my tongue. She moaned softly. I was careful to take my time, not wanting to rush this. As I slowly moved in circles around her tit with my tongue, I moved upward toward her sexy brown areola and her pert deep pink nipple. As I reached her areola, I changed my tongue motion to a flickering of the tip of my tongue over her. Here I was, leaning over my boss sucking her tit into my mouth….my cunt was dripping! I took her nipple into my mouth and suckled it, gently flicking it with my tongue and then sucking harder, my tongue milking her breast into my mouth. Deeper and deeper I took her soft, fleshy breast until my mouth was full. I alternated sucking hard and softer, eliciting a steady stream of moans and sighs. I moved to her other tit and did the same exact thing. By this point I knew she was putty in my hands. I smiled at her as I moved slowly down her body. She looked at me with eyes that told me she needed release.

I grasped the waist band of her panties and pulled them down. She lifted her buttocks to enable me and then lifted her legs so I could pull them completely off. I ran my hands up the inside of her legs and thighs and pressed her legs apart. She was shiny with juices already. I took both hands and ran them over her puffy, aroused lips and spread her apart, uncovering her pinkness. I leaned in and took a long lick from bottom to top. She was already so aroused I knew this wouldn’t take long and I wanted to taste her as much as possible. I took slowly steady licks, starting from just under her hole and ending by rolling my tongue around her clitoral hood. I did this several times and felt her body pressing against me. I moved my tongue to her clit and flicked it, then closed my teeth around it and tugged it gently, “OOHHH squirt”, she moaned, “its been so long.” She was breathing heavily now. As I looked upward, watching her face, I sucked her clit gently into my mouth, assaulting it with my tongue as I slowly inserted first one, then two fingers into her. She was warm and wet and tight. Her pussy squeezed my fingers almost immediately. I turned my hand palm up and curled my fingers slightly and began stroking that nubby, spongy skin inside of her. My tongue suckling her lips and clit as I did. She bucked against me and her hands grabbed handfuls of the pillows on the side of her head. I pressed deep and massaged her insides as I felt her cunt squeeze harder, harder and even harder still then in an instant she let out a long, low scream and her cunt released sending a torrent of juice over my lips and tongue. I lapped at her juices as gush after gush seeped out of her. Her hips rocked feverishly at first, humping my face and then she slowed, occasional shivers running through her body as I licked her up. She laid there panting and moaning. A smile on her lips, eyes slightly closed. I moved up and kissed her softly, letting her taste herself. I picked up the sheet and covered her up. “Sleep well” I murmured as I left her in her wet spot and went off to the bedroom…

wanderer390hot 67M
52 posts
10/8/2011 5:26 pm

reach out squirt


wanderer390hot 67M
52 posts
10/8/2011 4:45 am

i would be happy to help if you like


iwant2squirt2 52F
24 posts
9/29/2011 6:18 pm

Thanks! Glad u enjoyed it!


CTblackdick 51M

9/29/2011 8:59 am

Wow great story!!


ironbed26 61M

9/23/2011 5:24 am

Im just 10 minutes away. Let me know when you want to be licked and fucked like a real man can do.


iwant2squirt2 52F
24 posts
9/18/2011 5:35 pm

Hehehe...well its just fantasy, but in my fantasy Hell yeah! LOL....though I did have a boss once who I asked for a raise and ended up pregnant...LMAO


6869chvl 59M
5 posts
9/18/2011 12:51 pm

awesome, Did you get a raise?


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