14 years ago I posted a couple of stories from my first sexual experience, which…
Her Mistress – Part One
Her Mistress – Part One
Betsy is a professional woman, a few years older than me, and very unhappy in her marriage. She said her husband was not good in bed, calling him a “2 minute Charlie”. We first met at a business function. She had a terrific smile that attracted me, along with a huge set of tits. She was also pleasantly plump and a super flirt at that.
As we left the business function she unexpectantly came up to me while I was opening my car. She put her arms around me and gave me a long and sensuous kiss, rubbing her body up next to mine. My 7″ cock got hard immediately and I knew she knew it. Betsy said, “We need to get together real soon. Free up an evening for me and I will pay for the hotel room!” Then she walked away, got into her car and left.
I was perplexed but turned on immensely. No woman had ever thrown herself at me before the way she did. I called her the next day and she repeated her offer. We set a date on the calendar. She told me to bring some red wine.
That evening after work I hurried over to the hotel. She must have been watching and called me on my cell before I even finished parking the car. “Come up to Room 223 and hurry!”
With the package of red wine, I climbed the steps and found Room 223 and tapped gently and the door came open. As I walked in, sitting on the bed nearest to the window was Betsy and a pretty lavender teddy. On the table was a plate of fruit. I came over and sat down on the edge of the bed and she immediately swooped over to me and clasped me and planted another long sensuous kiss. As she pulled away she grabbed the bag of wine with one hand and rubbed my fully erect cock with the other hand. “Do you want a snack first or do you want me first?”
Since I hesitated a second, Betsy said, “I will decide!” At that she jumped off the bed and walked around and took off my shoes and socks. She then commanded me to stand and as I did she proceeded to unbuckle my pants and remove them and my shirt, leaving me in my underwear. “What’s fair is fair!” Becky said.
She grabbed the bottle of wine and proceeded to uncork it and pour us both a glass. I started to move to help her and she said, “No you stay or the bed and keep staring at my ass!” Betsy then grabbed some grapes and strawberries and started to feed me while we sipped our wine. After a few more pieces of fruit and finishing the first glass of wine, Betsy jumps on the bed next to me and pushes me down on my back. She then lay next to me and again starts to kiss me and as I try to start to fondle her, she says, “No, you are mine first! I am going to take you first then you can have your way with me. I have fantasized for this moment a long time. You do not know how long I have been secretly craving you from a distance before I got up the nerve to approach you the other night”
Not wanting to ruin her plans, I remained still on my back while she kissed me and started rubbing my cock again. She pulled off my underwear and dropped her face onto my cock, alternately licking my balls, cock and inner thighs. As I started to moan as my orgasm started to build, Betsy took off her teddy and dropped her breasts onto my face, slipping on top of me with my cock between her thighs. I could tell she recently shaved, and whatever the lotion she put on her skin, it tingled against my cock held tightly just below her pussy. My cock was close enough to feel her heat and pussy juices, but not near enough to Nirvana. Betsy started kissing my neck and my nipples, biting them lightly and keeping a rhythmic stroking of my cock with her inner thighs. Suddenly she grabbed my cock and said, “Okay, my turn first!” She inserted my cock in her pussy and started riding me like there was no tomorrow. I never had any woman ride me that forcefully before. Because of her position and the force of her rhythms, I was not able to move at all – she was in total control. I could feel her pussy alternately contract tight against my cock and hump me like there was no tomorrow at the same time. She warned me not to come before her and allowed me to start grabbing and sucking her 38DD tits. As she picked up the pace and her breathing became labored, she actually pushed her chest further down on me, almost smothering me in ecstasy. Suddenly she started to cum, and she screamed so loud I am sure anyone in another room could hear her plainly. She bucked so wildly on top of me that it was painful and pleasurable at the same time. Her pussy contracted so tight against my cock I could not cum myself. After what seemed like two minutes, she exhaled and fell off to my side, with my cock still at full attention! She must have realized what had NOT happened for me, because she then took my cock into her mouth, deep-throating me and sucking me off with a vacuum-like sucking action that was a wild turn on – the best blow job I ever had.
Betsy asked for more wine and I got up filling our glasses and bringing the plate of fruit over to the bed. I started to feed her some fruit and she asked me to grab a towel. I got up and I felt her eyes staring at me both ways from the bathroom and back. Betsy asked me to bend over again, and pick up her teddy off the floor next to the bed. As I did, she started to massage my butt cheeks and this was a wild turn-on for me. No woman ever touched me there before and I must have moaned with pleasure. She then told me to lie face down on the bed and she gave me a pillow for my head and propped up my ass with another pillow. As I lay there, she started to massage my ass cheeks again, making round circles and light tickling and then she came closer to my anus. I gasped as her finger played with my asshole, then I felt her soft kissing my ass cheeks and reaching around to fondle my cock getting erect again. This must have been turning her on, because she said, “You haven’t had your way with me yet as I promised.”
I told Betsy, “Don’t stop what you are doing, I like it even if it is the first time someone ever touched my ass.” Betsy continued to soft kiss my ass cheeks, rubbing my cock, then she again returned to my anus, gently inserting the tip of her finger. Being a butt virgin, I was at first squeamish and in a little pain, but she said, “Relax your muscles and it becomes easier.” I did so and she gently inserted one finger fully into my anus, moving in and out and then she inserted a second finger which again hurt at first but then the pain turned to pleasure. She then slipped a third and fourth finger in my anus over the next few minutes, keeping a steady stroke in and out with one hand and continuing to pull and stroke my cock with the other. She said that a girl friend of her taught her how to give a prostate massage and starting maneuvering her four fingers inside my butt to such a way that I was screaming in pleasure and she knew my orgasm was close.
Betsy suddenly pulled out her four fingers and told me to lie back once again. For some reason, I immediately obeyed my older lover, getting on my back. She propped up my ass with two pillows. She went to her purse and pulled out her hair brush saying, “I need a new brush anyway!” She reached into her purse and took out a trial size of lotion, lathered up her brush and my anus. She then said, “Relax your muscles again as I insert the hairbrush handle into your butt.”
I reluctantly obeyed and the initial insertion was painful but I relaxed and it became enjoyable as she moved the brush in and out of my ass. Betsy then again mounted me and started to rotate her hips again and continued to move the brush in and out of my ass. “You can come any time you like now”, Betsy purred as she picked up the pace of both her fucking my cock and my ass simultaneously.
Within a few moments my orgasm built and I cummed for what seemed like several minutes, bucking my hips upward against her pussy while having a hair brush pushed in and out of my ass. What a mind blowing experience
. We both collapsed again on the bed side by side, the
brush still stuck in my ass. Betsy said, “I see that you are in for some pegging!” Not knowing what this was, I said, “If it is anything like what you just did for me, I am all for it.”
Before our evening was over, we did fuck again in the normal manner with me on top. I think Betsy wanted to make sure that I was still a normal guy or something like that. We made a date the following week and she said this time I would get to taste her other love nectars and get pegged.
My curiosity is overwhelming…