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My First Ever

Posted by: Author: Age: 23 - now Posted on: 7 comments
9 likes 17276 views Category: Masturbation Female-Female Tags: friends mom, kiss, titties, cunny, boss, pleasing, Doctor, incest, sister, japanese, first time with sister, mutual, watch, caught
This is still a very potent memory and my favorite when I'm jilling.

This is the story of my first ever sexual experience with another person. It was amazing and delightful and formed the basis for much of my sexuality now. I'm sure that after you read this you will understand why I like older women so much... I had just turned 18 when I was invited to go to a very fancy party. I didn't have a dress to wear, or at least I didn't want to wear the ones that were in my closet. My best friend, Katie, had a beautiful red dress that she offered to let me wear. I had seen her in it and I immediately agreed. The Saturday a week before the party, I went to Katie's house to try the dress on. I wasn't too worried since we wore the same sizes and pretty much shared all of our clothes. Katie wasn't there that morning as she had gone with her father and brother out of town for some reason. Her mom, Margaret, was there, though, and she was expecting me. Katie and I had been best friends since fourth grade and had done lots and lots of sleepovers at her house and at mine. We had no great secrets from each other and were totally comfortable in each other's house. Her mom told me to just go into Katie's bedroom where the dress was hanging from the door for me to try on. She said that she would be in in a minute to zip it up for me and to help me. I took off my shorts and tee. I was wearing the bra that I would wear under the dress, so I took the dress off the hanger and pulled it on, settling it over my shoulders. Her mom came in and zipped it up and fussed with it a little bit, pulling the skirt into place and fluffing it up. It was a lovely dress. It had short sleeves that puffed at the shoulders, a jewel neck, fitted bodice and a very poofy skirt to my knees that was held out by a crinoline underskirt that was attached inside. I walked around the room and checked it out in the mirror and took a twirl, liking the way the skirt went out when I did. Margaret held out a pair of red pumps that were dyed to match the dress and I sat down to try them on. She knelt down in front of me and helped me get them on. After she did the buckle on the straps, she briefly caressed my calves and told me that they would make my legs look heavenly. Her touch was very nice and a surprise to me. I liked it though and didn't say anything. I stood up and walked around the room, admiring how nice the dress looked. "It's pretty scratchy with that net stuff underneath, Mrs. Smith" "Yes, the crinoline is pretty scratchy, but when you're wearing hosiery you won't notice that. You are wearing hose, aren't you?" "Yes, mom got me some dark pantyhose to wear with this. You're sure it won't scratch me to death?" She chuckled, "Don't worry, dear, it will be just fine." With that, she invited me to the kitchen for iced tea. I walked after her in the dress, enjoying the way the skirt moved around my legs. We sat down at her kitchen table and she brought two glasses of iced tea and we sat chatting about school, friends and boys. She was wearing a loose, low-cut halter top and I found that when she bent over a little I could see some of her tits. I didn't know why that fascinated me, but I found myself staring down her top. She noticed it, too, and asked, "Do you like what you see?" I was flustered and embarrassed, but I nodded and said, "You're very pretty, Mrs. Smith" She smiled, "Do you really think so?" "Oh, yes! I always thought you and Katie are so pretty." With that, she leaned over and kissed me on my lips. I was shocked. She did it again, this time staying a little longer and then she opened her mouth and put her tongue in mine. I was very shocked, but my pussy was immediately soaked and I was very horny. I couldn't help but let my tongue play with hers and I kissed her back. She held the kiss for a moment, caressing the back of my head. She seemed to come to a decision. She stood up and silently offered me her hand. I got up too and gave her mine. She walked me to her bedroom, closed the door, and pulled me into a hug and kissed me again, deeper and more romantically. I had never been kissed that way but it was making me light-headed and totally soaked my panties. I couldn't believe how this was going, but I loved every minute of it. I went crazy, kissing her as she kissed me. It was heavenly. She told me that we should take the dress off me so I didn't get it messed up before the party. Before I knew what was happening, she unzipped the dress and pulled it off my shoulders. She carefully put it on a hanger and turned back to me. She kissed me again and backed me against the bed, making me sit down. She knelt down again and undid the shoes, tossing them on the floor near where she hung up the dress. She sat on the bed with me and kissed me again, letting her hands wander over my back, my butt, and my titties through my bra. I began to explore her too. I touched her tits through her halter and her butt and thighs through her shorts. She stopped for a second, looked into my eyes, and said, "You don't have to do this, you know." I just kissed her harder and told her I wanted it very much. She then laid me down across her bed and laid beside me. She was kissing me everywhere as she unhooked my bra, letting my titties free. She seemed to be delighted in them as she spent quite a bit of time kissing, sucking, and nibbling on them. I didn't realize until then how much they were connected to my pussy, but I almost came from her playing with my hard nipples. She tugged on my panties and I lifted up my hips to let her take them off of me. She said a lot of nice things about my cunny. I was a little embarrassed but very horny by this time. I opened my legs for her a little and she quickly took advantage of me. She touched my legs, my thighs, my inner thighs, up to my pussy. She made sure that she left no part unkissed or unlicked and she made me cum. When I recovered, she was lying beside me and I saw that her clothes were all off her now. She must have taken them off when I was cumming and recovering. I rolled toward her and kissed her and started to touch her everywhere like she did for me. Her titties were bigger than mine, maybe 36B, and they had nice big nipples on them that were sticking out a mile or so. I couldn't help but take one in my mouth and suckle on her a little. She gasped and held my head to her tit. So, I kept licking and sucking her nipples. She was moaning as I did so. I pushed my knee between her thighs and was amazed at how wet she was as she rubbed her pussy on me. It didn't take much of this before she had a delicious-sounding orgasm of her own. We made love for another hour or so, enjoying more orgasms together. She finally had us get up and we had a shower together where we played even more. I pulled on my wet panties and bra and found my shorts and top in Katie's room. Margaret had put the dress in a dress bag for me with the shoes and kissed me before she opened the door. She reminded me that I had to keep this a secret just between the two of us and I totally understood. Since then, Margaret and I get together whenever our schedules allow. That works out to about one day in 3-6 months but it is always special and we always plan interesting things to do and fun places to make love together. To this day, I have never told Katie or anybody else about my older mom friend. I always pay attention to my elders, though. I never know when I might find a willing teacher!



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