Teen Girl and Older Woman – a Lesbian MILF Fantasy

The sun was bright and caused me to squint as I looked past Johnny’s head. I could see the sweat beaded across his shoulder. He pulled back and we looked into each other’s eyes. He knew he was pleasuring me greatly…

My pelvis was tilted forward because we were on the beach. The mound of sand under my lower body was unyielding and caused our angle to be different than ever before. The angle caused him to have pres-sure against my g-spot. This was a totally new sensation for me and was absolutely heaven. I could feel the sun warmly shining on my thighs. They were spread wide on the blanket we had laid upon the sand. Johnny had pushed my bikini top up over my firm breasts. My nipples are almost always erect and they brushed roughly against John’s chest as he pressed close to me after every thrust.

“Ooohhhhhhhh…” Johnny had again slowly thrust the head of his cock against my g-spot and the spasm shuttered through my body. My bikini bottom was still gripped in my left hand from when I had desperately pulled it free. I had both my hands on Johnny’s cheeks, guiding his speed as he slowly thrust in and out – stopping him each time another orgasm poured warm surges through my legs.. Johnny was wonderful at following my lead… He was very sensitive to my desires and aware of all of my urgings. “Ooohhhhhhh…” Again I guided him as he worked inside me…

*

I had been lying in bed thinking about my trip to Kauai. Johnny and I had spent two weeks exploring the island, spending most of our time on the huge beach on the northwest coast. The beach is 17 miles long and hundreds of feet wide. Some days we never saw anyone else – had the place entirely to ourselves. We took every opportunity to explore the island…and each other. This was the summer after my senior year in high school. I was 17, a fully developed curvy thing of 5’4″, 35/22/33. My mother had smartly put me on the pill (of course to control my cycle! >giggle<) and my normal C cup was straining to accommodate me. I filled out a bikini very well in those days (still do as a matter of fact...). My grandfather had given the trip to me as a graduation pre-sent. It was a wonderful trip that I will never forget. I was a young girl in fairy tale land... * As I was lying there in the dark, my hand down in my panties helping with my memories, I saw a light come on in the house next door. That was curious since I thought the house was empty. I moved over and looked down into the lighted window through restless branches in the trees. My parent's house was perched on a hill. The neighbor's house was also on the hill, but set lower down. I could see a woman's figure near the window. I quickly knelt back away from my window for fear that she would see me peering down at her. As I edged back up to the window, I saw a beautiful woman standing in the room wearing a stark, gray business suit. She looked to be in her late twenties or early thirties, jet-black hair and about my height. There were several packing boxes on the floor, most of which were still taped shut. She took off her jacket and laid it on the bed. She had on a pink silk blouse, which was semi-transparent. Her breasts were large and I could just make out the outline of her nipples beneath the material of the blouse. She removed the blouse. She wore a pink camisole with thin little straps and no bra. I gasped as she reached and pulled the camisole over her head, her breasts stood high and firm with almost no sag. They were very round and full, not pointed at all and the nipples were quite large and a very dark ruby color. She stood looking at herself in the tall full-length mirror. Very slowly she moved her hands to the underside of her breasts, closed her eyes and began to massage and gently pull at them. Every once in awhile, her hands would move to her nipples and she would roll them gently between her fingers. I was getting excited at the sight of this woman caressing herself. I was already wet from playing with myself while thinking about Johnny's attributes. Thoughts of my old girlfriend Mandy quickly flashed before me. I had not thought about another female in quite some time, but this lady in the window was really arousing me. She was stunning. As she continued to fondle herself, I slipped my hand into my panties again and slowly rotated my middle finger around and around my clitoris, sort of following the motion of her hands. I was having a hard time balancing myself as I knelt on the bed and stretched to see her. I got off the bed and went to my door and quietly locked it. I pulled off my robe and slid my panties off and left them lying on the floor. (Voyeurism is such a turn-on) Then I moved back to the window and saw that she was unbuttoning her skirt. She let it fall to the floor and reached over to pick it up. She had on white, shimmering brief type panties, a garter belt and natural colored stockings. She moved out of my sight for a moment as she hung up the suit. She came back to the window, crossed over and turned on a small, dim bedside lamp, switching off the overhead light. It was very hard to see into the room now between the dimmed light and the ever-swaying branches, but I kept at it. She pulled the covers down from the bed. I could see her out-line in contrast to the white sheets as the light reflected off her body. She lay back on the bed for a while. I saw her legs spread slightly. (It was very hard to see) Every once in awhile I would see one leg move from side to side or bend up. I could only imagine what she was doing - probably the same thing I was doing. I gave up trying to see down into the room. I lie back down on my bed and continued to roll my clitoris, back and forth, round and round. I pulled a pillow between my legs, pressed it to my chest and soon climaxed. "Ooohhh..." I fell asleep, visions of Johnny and this new curiosity next door, her, then him, then her, mixing and ebbing... * I asked my mother the next morning about the new neighbor. She said that a couple had moved in a few days before. They were just renting and expected to stay about a year. He, Jim, was with the government and on assignment to the Far East. He would travel back and forth, normally two weeks at a time. She, Shelly, was an attorney, specializing in contract law with big corporations. She was in the process of interviewing. They had no children. My mother said they were invited to dinner tomorrow evening and that I should plan on being there. I looked forward to the meeting. * They showed up early and I was not ready, so I wound up making a "grand entrance" - something I hate to do. I am pretty shy. Jim was average in height, trim and had great eyes. He was dressed comfortably in slacks, golf shirt and a cashmere sweater. His greeting was very warm. I could tell he was a nice guy. Shelly had a wonderful smile and great eyes also - very alert and penetrating. She looked very deeply into my eyes as we were introduced. She seemed bright but mischievous! Seeing her up close like that did nothing to diminish my first impression was that she was stunning...but she also seemed genuine. She was wearing a silk pants suit with no sign of underwear. After seeing her the other night, I was certain that there was no need for her to support anything! I looked over at my father. He was staring. I looked at my mother. She was staring! Ha! I'm sure my brother would have been drooling had he been there (he was away at graduate school taking one last summer class). Throughout dinner we exchanged all of the family tales. They were most recently from the New England area and were glad not to have to spend another winter there. At one point my mother commented on the silk pants suit that Shelly was wearing. Shelly said that she had made it herself, that it was a hobby of hers and that she had a whole closet full of things she had done, or, at least she would have as soon as she could finish unpacking! I told her that I would love to see what she had made. She seemed to light up and said she would love to show them to me. She said that Jim was leaving for a short trip tomorrow and that she would love to have company as she finished un-packing. Her eyes sparkled and captivated me. We seemed to "click" and it seemed as though I had found a new friend. She was older of course, but so vibrant and exciting... We finished dinner and Jim complained about having to get up early for his flight the next morning. They politely begged off dessert and left shortly afterward. I was also tired - still recovering from my Hawaii trip. I kissed Mom and Dad goodnight and headed to bed. I pulled off my clothes, grabbed a nightie and jumped into bed. Just as I leaned over to turn out the light, I saw the light go on in Jim and Shelly's bedroom. I quickly turned off my light... Shelly was staring at Jim -- a huge smile on her face as she slowly unbuttoned her top. As I suspected, she was braless... her nipples stood out hard against the milky white of her beautiful, firm breasts. She reached behind her and worked at the back of her pants. Soon they fell to the floor. I was wrong there though. She had on a pair of silk dainty boxer shorts from material that looked like the same as the suit. The sight of her was getting me hot and I slipped my hand down and started to rub my clit, going a little further down to steal some of my quickening wetness for lubrication. I have always gotten ready very quickly and I flow heavily... sometimes causing sort of a problem with some of the smaller guys I have been with. This night was no exception - I was very wet, very quickly... Jim came closer to her as she stood there in her sorties. She was cupping her breasts and slowly kneading them together and then apart, together, apart...her eyes glowing at him all the while. He had taken his sweater and shirt off and was undoing his trousers. He was sideways to me and it was obvious the effect she was having on him. I thought he said he was tired! I quickened my pace as he slid his pants down - it was he who did not have on underwear! His cock was very hard, standing straight up against his very bushy pubic hair. He was not exceedingly long, but was thicker, broader than any of the guys I had been with (which at that time was just a couple). He stepped out of his pants and moved closer to her. She let her hands fall from her breasts to the sides of the shorties and slowly, and I mean slowly, inched them down over her hips. Oh - she was magnificent. I came for the first time as I saw the shorties drop from her hips and watched as she moved her hands quickly to her crotch and used the middle finger of each hand to press both of her pussy lips together. She spread her legs slightly and continued to press, then release her lips, press and release. I mimicked her action and my knees buckled as another orgasm flooded through my loins. "Ohhhhh..." my head started to swim and I settled back against the bed, kind of half sitting there as I continued to massage my clit, over and over and over again. I slipped one hand down further and a finger found a very warm, wet place to work. I pushed my finger in deep and found my g-spot, the place that Johnny had discovered for me just a few days be-fore. I almost passed out as my finger found its mark - I was already very sensitive there and did not have to go through the "learning" that some of my girlfriends have told me about. I came once again and lay back on the bed and just held my hands still, pressing into my-self. All my nerves were raw. I could not move. I just lay there panting and pressing my hands against my pussy as I continued to come. The last thing I remember thinking about was the wet spot on the bed where my buttocks rested against the edge of the bed. Exhausted, I rolled onto the bed and quickly fell asleep with visions of Shelly and John dancing in my head. * I awoke sometime later and looked out the window. The night was clear and the stars were very bright since there was no moon. Their bedroom light was out and I couldn't see anything as I stared down into the window. As I turned to go to the bathroom I thought I saw someone move in the window. I stopped and stared, but saw nothing. * I was a little upset that I missed most of Jim and Shelly's escapade the night before, but realized that I must have been very tired from the trip back from Hawaii. I spent most of the next day shopping with my girlfriend - Kathy. We found a really cute dress that looked great on me but was just a little too big in the waist. It is hard for me to find things off-the-shelf that fit well, particularly then. I thought of Shelly. Maybe she could bring it in for me. I took the dress with me when I went over to Shelly's that evening. I had taken quite awhile to get ready -- I wanted to look especially nice. Though I had kept my eye on other girls since my experiences with Mandy several months ago, I think that I had convinced myself that they were just curiosities that all girls go through. I do not believe I thought of myself as bisexual back then. I certainly did not think about it in reference to an "older woman". I just wanted to look nice because she was so beautiful. I knocked on the door. No answer. Uh oh, did she forget? I had not seen her car when I got back from shopping. She had a 928S that was in the driveway when I left to go shopping that morning. I was very disappointed...I was so looking forward to spending the evening with her. Every time I thought of her I saw those big, bright eyes. I rang the bell. No answer. I was turning to leave when the door opened. She stood there in a huge bath towel that she had pulled around her front. "Hi Sally! I was in the shower," she said with her eyes bright and full of life. "I was unpacking and just lost track of the time. Come on in and grab a couple of glasses and some wine." Everything she said seemed punctuated with vibrancy I had never known. I closed the door behind me. "It's in the dining room...what's that?" she motioned to the dress I was holding. "Oh... I bought it today and was hoping that you might help me with it. It needs a little work." "Sure. Bring it up with you," she said as she turned towards the hallway and simultaneously pointed toward the dining room. As she turned, I was presented with her naked backside. She had only pulled the towel across her front. As she went away, I could see her dainty, firm cheeks jiggle as she trotted off. She, like Mandy and myself, was very curvy through the hips with a low waist that melded with her hips in a very gentle, even way. "OK..." I said catching my breath. I lost sight of her as she went down the hallway to the stairs. I looked around at the foyer and went into the living room. The furniture was contemporary, very stylish and obviously expensive. It looked so much better than the oriental motif that the previous owners had used. There were pictures and boxes propped against all the walls. She still had a lot left to do. A stereo was on and playing fairly loud jazz. I crossed to the large dining room and saw a case of wine sitting on the floor. I did not know anything about wine then. It had French writing on the label and I could see that it was a white Riesling from Alsace. I had no idea what that meant, but I wanted to savor everything about Shelly, so I made a point of remembering it. I did not see any wine glasses. I just grabbed a couple of tumblers I found. I went past the kitchen and bound up the stairs with a feeling of excitement and adventure. There was only one room with a light on at the end of the long hallway...I entered and called "Shelly?" "In here." I moved to the master bathroom and she was brushing her hair. It was pure black and very long, almost down to her waist. I had only seen her with it up. She was in a shortie robe which was only loosely tied. She also had on her usual smile. She said, "How about that glass of wine -- I could really use it!" I placed my dress on a chair near the door and set the glasses on the marble counter. All of a sudden I realized that I had forgotten to bring a corkscrew. Anticipating, Shelly laughed at me in the mirror and said "Jim always forgets too - there's one in the nightstand on this side of the bed." I went over and slid the drawer open. There was the corkscrew alongside a small ivory colored plastic vibrator. I had seen ads for them before, but never a real one. I grabbed the corkscrew and quickly closed the drawer. The bed was large. The room was large. I looked at the window that I had spied on them the night before. It was open to the night air and the drapes swayed in and out against the onshore breeze. Shelly had pulled on a pair of cashmere, clingy pants and was buttoning a matching short-sleeved top. It was obvious from the tightness of her clothes that she had no underwear on beneath her little suit. The thrust of her full bust and the nipples pointing through the fabric once again showed what a great, firm body see had. She had on a beautiful pair of amethyst earrings and her eyes beamed widely. She opened the bottle of wine, poured, and toasted our new friendship. She was so poised, so smooth. "So, what's wrong with the dress?" "It's too big through the waist. It's real hard for me to find things that fit me well." "I can see why." as she laughed and looked me up and down. "I have the same problem. You look like almost the same size as me. You've got a great body! Why don't you slip the dress on and we'll have a look at the fit." I picked the dress up off the chair and walked into the bathroom to change. I took off my shorts and t-top and noticed that Shelly was watching me. I had on a pair of semi-see-through pink bikini panties and a matching bra. I bought them that day. As I was standing there in my underwear looking back at Shelly, my normally firm nipples became very erect and pressed hard against the thin material. She smiled at me and turned away. I slipped the dress on. It was a simple little short summer dress with a fairly low cut bodice that buttoned up the front. I bought it thinking of Johnny. He loved to see me dress sexy. I walked back into the bedroom and Shelly had moved across the hall to another room. There were things lying around everywhere, but it was obvious that this was going to be her sewing room. A radio in the room was tuned to the same station as the stereo downstairs. Shelly filled my glass and told me to stand up on the stool that was in a corner of the room near a comfortable looking sofa. I moved to the stool and was looking down on her now, her brilliant black hair shining in the brightly lit room. As she came closer, I could smell her perfume. Very faint...White Shoulders I found out later. She took her hands and slowly moved them up to my armpits, hands extended. She placed them between my arms and the sides of my chest and moved them down along the outside of my body, stopping just as she reached the top of the swell of my hips. She opened her thumbs and moved them down across my stomach so that she was holding my waist. Her thumbs rotated downward just a little more and I let out a faint gasp. She looked up at me and smiled a mischievous look back at me. She was so pretty. She grabbed a pin box and began to pin one side. As she moved her hands one of them lightly brushed against the underside of my breast. I tensed. I was nervous and excited at the same time. The wine, the perfume and the music were intoxicating. She was intoxicating! Her hands moved all over my sides and waist as she continued to pin in the sides. I could feel the warmth of her hands, ever so lightly. It was hard to stand still. I would sway occasionally and needed to brace myself by placing my hand against the corner wall. "There...that takes care of the waist. What about the length?" With that, she turned her palms inward and slipped her hands up underneath the front of the dress and placed her thumbs on the hem in front. The light touch of the back of her hands brushing against the hair on my thighs sent a chill through me and I once again let out a little gasp. It was just a rush of breath, but we both heard it and I became flushed at once. It felt like my whole body was on fire -- her beautiful face, the wine, her hands lightly touching my thighs. My knees buckled slightly and I had to put a hand on her shoulder to keep from falling. Shelly then turned her palms around toward my thighs and slowly traced her hands from my knees upward. She wasn't really touching my skin, but only light enough to brush the soft hair on the front of my legs. Slowly upward she inched. My breathing became quick now....the sensation of her oh-so-light fingering on the front of my thighs was burning through my legs. I bolted down what wine was remaining in the glass and let it drop to the carpeted floor. I put my other hand on her shoulder to keep myself from falling over. "I saw you watching me the other night when I was in my room - and again when Jim and I were there last night. Did it excite you?". She teased me with her soft voice. Oh my god, she HAD seen me. "Uh, ... you saw me?" I didn't really know what to say. Her hands continued their slow steady climb up under my dress and stopped just at the leg band of my panties. "Did it excite you, Sally?" she repeated. I paused - unsure of what to say. "Yes!" I finally let out in a whisper. "Did you play with yourself?" With that she slowly moved the fingers of her right hand across the outside of my thin panties and pressed against my pubic mound, while her thumb slipped down under the leg band of my panties and edged its way in between my legs and found my clitoris. My knees again buckled, causing my legs to spread slightly. "Sally..are you enjoying this?" she asked as she gently moved her thumb in and out over my clit. "Oh my god! YES!" I shouted. I realized how loud I was and quickly put my hand over my mouth in a desperate attempt to muffle my outburst. Shelly then withdrew her hand and placed one at the top of each side of my panties and slowly pulled them down. She did every-thing so slowly. I was burning up -- on fire -- and each deliberate motion of hers drove me insane. She slightly lifted my feet up one at a time as she pulled the panties completely off. I could barely stand up. She lifted the skimpy panties up to show me that they were wet. She once again looked at me with those mischievous eyes of hers. She was definitely having fun with me. "I didn't say anything to Jim, but thinking of you there watching really excited me." Shelly began to unbutton the front of my dress. Again, one button at a time - very slow, very deliberate. "You don't want me to quite do you, Sally?" Rather than speak, I answered her by moving my hands to the front of her top and mimicked her motion as I slowly unbuttoned it. I got all the buttons undone just before she pushed my hands away in order to slip my dress back across my shoulders, down my back and over my buttocks, letting it fall and leaving me standing there in only my bra. I stepped off the stool and similarly pushed her top off. Her breasts jiggled slightly as I forced the top off, her nipples rigid and a very deep red. Shelly's breath then quickened as I lightly cradled her breasts, one in each hand. I took one nipple in my mouth and slowly caressed it with my tongue. She reached and unclipped by bra in front and my breasts sprang free as my bra fell open and dropped to the sides. She again pushed my hands away as she pulled the bra away from me. The room was spinning now, both of us breathing fast as she lifted my head and moved very close, causing our breasts to press together ever so slightly. Shelly embraced me and I felt her hot breath on my shoulder as her arms encircled me. I slipped my hands into the elastic waistband of her pants and pushed them down over her hips as we separated slightly to allow them to drop to the floor. I was so wet and my loins ached, Hot? I had never felt like this before, I was ready to explode! And from the look in Shelly's eyes, she was very excited too. "Sit down on the sofa, Sally." she said as she moved over to the light switch and dialed the dimmer so that there was just enough light for me to see her outline. She came back over to the sofa and knelt in front of me. "You are so pretty, Sally." I tilted my head back on the back of the sofa as she placed her hands on the inside of my calves and forced my legs apart. A breeze swiftly entered the room through the open window and I felt coolness in my crotch as she spread me wide. I was dripping wet in anticipation. "Ohhhhh..." I sighed as Shelley slipped a finger inside me. She kept pressure on the front inside wall of my vagina as she moved her finger further into me. As she hit my g-spot, I finally did explode - shudder after shudder after shudder. I came again and again and again as she thrust her finger over my g-spot. She took my right hand and pulled it down to my crotch. "Do yourself, Sally." I tilted my head, looked up and peered at her through my barely open, watered eyes. I could see that her other hand was down between her legs and her breathing was very fast as both hands were moving in a cycling motion - one in me and the other in herself. I began to press my index finger in circular fashion around and around the outside of my clit. I put my other hand to her breast and gently squeezed the nipple. Again I came as my hips bucked forward in response to our probing fingers. I again laid my head against the sofa back. I soon felt her hair touching the inside of my thighs. I pulled my hand away as I felt the nearness of her mouth. She pushed my legs wider apart with her shoulders as I felt her mouth close over my cunt. "Oh my god....", I shouted again as her tongue lapped full against my pussy lips and spread them wide -- the tip of her tongue moving from the point where her finger entered me, up across my lips and settled on top of my clit. It darted lightly around and around my clit, but she was very deliberate again - and maddeningly slow. Each time she hit the bottom of my inflamed clit, my hips involuntarily jumped forward. I jerked up as I heard a loud voice shout, "Why you little slut!" I tried to drag my senses back but I was so overpowered with my body's deep involvement in our sex. I struggled to open my eyes and saw Shelly's husband Jim looking into the room from the doorway! My god, I was mortified. Shelly pulled quickly away as we heard Jim say, "She's just a kid, Shelly. My god, what are you doing?" I looked at Shelly, but she had pulled away and was just kneeling there - staring at him. I got up trying to cover as best I could as I grabbed my dress from the floor. I stepped into it and pulled it up. I held it closed in front as I bolted past Jim who had moved out of the doorway. I could not look at him. I headed down- stairs toward the front door and heard Jim yell loudly, "Jesus Christ, Shelly!"... * I found out later that Jim's meetings had gotten over early and he was able to get a late flight home that night - a day early! I saw Shelly several times that summer before I moved to my dorm for the fall semester of my freshman year of college. We spoke openly of the episode. She had promised Jim that she would not be with me or anyone else again. Shelly was bi-sexual, but Jim could not seem to come to grips with that lifestyle. I am not sure if they ever resolved their situation, as they moved away during my freshman year. I remember Shelly very fondly though. She was the one that convinced me that my attraction to other women is much more than a curiosity...

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