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When Tammy first approached me and asked me out to dinner, I nearly fainted. No one had ever asked me out before. I’m not really the sort of boy who attracts the attention of the opposite sex. At twenty years old, I stand 5’4″ and weigh just over 120lbs. Everything about me is small. I’ve been told I have a baby face with big blue eyes and a little button nose. I have thick, light brown hair with a natural wave to it. With my extremely fair skin, I’ve always stayed out of the sun which has left me very pale.
Tammy, on the other hand, was larger than life. In her late thirties, she stood six foot tall in the heels she wore. Her long, platinum blonde hair was pulled back in a thick braid that hung below her waist. She had breasts the size of cantaloupes, wide hips and thick thighs. Her bright red lipstick and black mascara were both applied heavily. And her fingernails were so long they extended beyond the end of her fingers by nearly an inch. When she asked me to join her for dinner, she spoke loudly and with supreme confidence.
During that first date, Tammy began comparing me to someone named Kerry. When I asked about it, she told me Kerry was just someone she knew. But she compared me to Kerry so often it made me feel funny. You’re just as cute as Kerry. You eat like a bird, just like Kerry. Kerry has long eyelashes just as like yours. You have the sweetest little lips, just like Kerry. Kerry doesn’t like fish either. It’s so cute, Kerry always tries to pay when we go out too. It went on and on.
After a very romantic dinner in a restaurant I’d never heard of, Tammy drove me to her home. It was a 40-minute drive and in that time, she peppered me with questions about my family, my education, my job and my lack of past sexual experiences. She was the sort of woman I couldn’t be dishonest with. She was so mature, beautiful, confident and smart. Whatever she asked, I answered with complete honesty. That was another thing I apparently had in common with Kerry.
That evening I gave my virginity to Tammy. It was fast and over far too quickly but I couldn’t help it. She was so big, soft and warm. It was perfectly lovely. She didn’t cum, I was too small and inexperienced to even get her close to having an orgasm. I spent the majority of those few precious moments sliding between her lips and occasionally getting lucky and poking inside of her with my stiff little penis. She never laughed or giggled. She held me in her arms and told me I made love just like Kerry.
Three nights later, Tammy took me out again. Over dinner in an equally romantic restaurant, she confessed that Kerry was another boy she ‘spent time with’. When I asked if they had sex. She smiled and told me they had. I asked if he was her boyfriend. She told me we were both her boyfriends. I began to pout and she told me that is how Kerry reacted when he learned about me.
The entire time we were at that restaurant, Tammy explained that Kerry and I were both very special to her. She said she’d met Kerry a day before she met me. She had taken Kerry’s virginity the night before she’d taken mine. She said she felt like the luckiest woman in the world to have two, cute, young men to play with.
As the evening progressed, I somehow stopped being so worried about Kerry and started to enjoy my time with Tammy. It probably had something to do with her hand on my thigh. Or maybe it was the way she kept kissing me right there in the restaurant. Her public displays of affection made me squirm! It didn’t hurt that she kept whispering in my ear, telling me how excited she was to get me back into her bed.
We wound up at Tammy’s house again that night and while we made love, she kept bringing up Kerry. She told me he humped himself against her just like I did. She told me he had a cute little penis just like mine.
It didn’t matter what she said, I loved climbing on top of her warm, soft body and sliding my penis between her lips and into her pussy. She was so big and I was so small. She was so confident and I was not. She was mature and wise and I loved her. Tammy held me in her arms while my penis slid around her big, meaty pussy. When my penis did manage to slide inside of her, I don’t think she could feel me. She never reacted at all. Those encounters were about me getting off. While at the same time, she was working toward a goal I knew nothing about.
Several nights later, Tammy took me out to dinner again. While we waited for our food to be delivered, she opened her giant purse and pulled out two, small gift wrapped packages. After looking at the labels, she handed one to me and put the other back in her purse. She told me the other package was for Kerry. She told me he’d get his surprise the very next night when they went out together.
I asked her again about Kerry. I wanted to know if they were as serious as we were. I wanted to know what it was she wanted. She told me they were just as serious as we were. He meant just as much to her as I did. It hurt to hear those words, bahis siteleri but I somehow kept from crying. I loved her so much that I couldn’t get upset with her for seeing someone else. I cherished our time together and never wanted to stop seeing her.
Tammy told me to open my present. So right there in the restaurant, I carefully opened the wrappings to find a pair of white bikini panties trimmed in lace. I wadded them up in my hands to hide them from anyone who may be looking. Tammy leaned in close, licked my ear and whispered softly. She told me to go to the little boy’s room and change into them. She told me she really wanted me to wear them for the whole night. To help me make the decision, she told me she knew Kerry would do it the next night when she gave him his present.
Not willing to be outdone by Kerry, I hid the panties in my fist as I made my way to the restroom. I chose the stall on the far end and quickly slipped off my shoes, pants, and underwear. I then slid the cute pair of white, satin panties up my legs. I stood there and admired the way my little hardon poked the panties out away from my body. After hearing noises outside the door, I quickly got dressed and washed my hands. Being unsure of what I was supposed to do with my boy briefs, I made a quick decision and dropped them in the trash.
When I slipped back into the booth beside Tammy, she immediately asked if they fit and how they felt. I blushed and told her they fit perfectly and they felt very sexy. She smiled and told me she knew I’d love them. For the rest of that meal, I squirmed beside Tammy while enjoying the feel of satin against my rigid penis. She let her large, warm hand slide onto my lap to be sure I was still stiff several times throughout that meal. After feeling my penis throb against her hand, she whispered things like, “I didn’t see a lump, but you are still hard!” or “I can never tell if Kerry has a little hard-on by just looking either. You two are so much alike!”
Tammy took me home with her again that night and we again made love. That time, instead of sliding between the lips of her pussy, she used body oil on her thick thigh and let me hump myself against it. In that position, I was able to kiss, lick and suck on her big, brown nipples while I humped my penis against her leg. It was amazing.
As I neared my orgasm, Tammy told me in a soft voice that she wanted me to meet Kerry. She told me it was time the two of us got to know each other. She told me we were both her ‘special boys’ and she loved us both. But when she was with Kerry, she missed me. And when she was with me, she missed Kerry. She wanted us to spend time together.
I squealed loudly that night when I squirted on her big, slippery, thick thigh. I lay on top of her gasping and trying to catch my breath as the spasm of my orgasm continued to rage through my body. Tammy pulled me into her arms and I slid along her thigh and through the creamy mess I’d made. She held me in her warm embrace and told me she knew Kerry and I would get along perfectly, we were too much alike not to.
That night, I didn’t commit to anything. I was starting to get the idea of what Tammy’s dream relationship was. She wanted to be able to take both Kerry and me out at the same time! All of my relationship experiences were with Tammy. She was the one and only person I’d ever kissed, not to mention the sex! I didn’t want to lose her, but I was afraid of what bringing Kerry along on our dates meant. Would she take us both home?
Tammy called me two days later and was anxious to tell me how Kerry had reacted when she asked if he’d like to meet me. Apparently, he said he would. He was reluctant and nervous, but he agreed to meet me. I had no choice, I had to agree to it too!
That next night Tammy picked me up and when she did, Kerry was already in the car. Tammy had me sit in the backseat with Kerry so we could get to know each other.
What was most shocking about that meeting was how similar Kerry and I were. He stood within an inch of my height, he had the same build and we must’ve weighed within a few pounds of each other. He had big green eyes, while mine are blue. He had a cute little nose just like mine. While my hair is light brown, his was a darker brown. When we shook hands, it was like shaking my own hand! His hands were soft and free of callouses too. We could have easily been brothers!
The conversation came very easy between the two of us. By the time Tammy pulled into the restaurant parking lot, Kerry and I were in the backseat having a great time! We all climbed out of the car and on the way to the restaurant door, Tammy asked each of us if we were wearing the panties she’d bought for us. With absolutely no shame, Kerry and I both chirped, “Yes!” at the same time.
Once seated in our booth, Tammy sat beside Kerry on the end, leaving him and I sitting together. Tammy told us both how happy she was that we were getting along so well. She said she knew we would. Glancing down between canlı bahis siteleri Kerry and I, she went on to say that she didn’t expect to see us holding hands so quickly!
Kerry and I both looked down and realized we were indeed holding hands. Neither of us made a move to pull our hands away. On the contrary, we squeezed each other’s hands and giggled. There was definitely an attraction between the two of us. And at one point, our eyes met and we held each other’s gaze. If the waiter hadn’t come along when he did, I’m sure we would have kissed.
Of course Tammy missed none of this. She could feel the sexual tension, just like we could. Kerry and I were both afraid of what we were feeling. Neither of us had ever had an attraction to the same sex. But the desire was unmistakable. I know his penis was just as stiff as mine. And Tammy’s pussy must’ve been positively drenched watching her two special boys flirt with each other so shamelessly.
After the waiter delivered our meals to our table, Kerry and I just nibbled on our food. Tammy ate slowly while enjoying watching the two of us interact. She paused between bites at one point and asked in a soft voice, “Peyton, is your little penis stiff?”
I whimpered softly. Looking first at Tammy, then to Kerry, and back to Tammy, I whispered, “Yes.” While squirming in the booth.
Tammy smiled warmly. Looking away from me to Kerry, she asked, “Kerry, how about you? Is your little penis stiff too?”
He stared at Tammy for several moments before glancing at me. His eyes lowered to my lap, then back to my face. He slowly turned to look back to Tammy before whispering, “Yes.”
Tammy smiled at both Kerry and I. In-between bites of her dinner, she spoke to both of us. She explained that she had been very nervous about our meeting. She told us she was very happy we were getting along so well. She really wanted to two of us to like each other and was thrilled we’d hit if off so well.
While waiting for the waiter to bring our check, Tammy suggested Kerry and I hold hands while she explained what would happen when we left the restaurant. After lacing our fingers together, Kerry and I looked at each other for a brief moment. I’m sure both of us had a very good idea about what Tammy was going to say. And I’m sure neither of us was considering leaving.
She said she’d never imagined she’d be lucky enough to find two, such special boys. She explained that we both made her very happy. And together, she knew the relationship would be magical. Tammy said she’d reserved a suite in a hotel just across the street. She explained that she wanted our first time together to be very special. Tammy looked first at me, then to Kerry. She told us she was thrilled she was finally going to have her two favorite boys together at the same time.
When the waiter arrived with our check, he stared down at Kerry and me for an awkward moment before handing the check to Tammy. It wasn’t until after he’d left that we realized we were sitting very close to each other and holding hands! We both blushed and giggled. While Tammy pulled her credit card from her purse, she told us she thought it was cute to see us holding hands. She suggested the two of us keep holding hands until we got to the suite she’d reserved.
As we slid out of the booth, Kerry and I kept our hands laced together. Tammy followed behind us as we made our way through the restaurant. Couples at several booths stopped talking and watched the two petite boys walk-by holding hands with larger-than-life Tammy right behind us. Once outside, Tammy leaned in between us and asked how it felt to be seen holding hands like that.
Kerry said something about it being embarrassing. I giggled and said it made my penis really stiff! Kerry looked shocked for a split second and then confessed his penis was super hard too. Tammy guided us to the crosswalk and we waited for the light to change while Kerry and I still held hands. We crossed the street and two cars honked at us!
When we arrived in the hotel, we walked by the valet, through the plush lobby and right past the pretty receptionist. Tammy guided directly to an elevator. Once inside, she used a keycard to access the top floor. None of us spoke. We were all lost in our thoughts. We stood in that elevator thinking to ourselves, imagining what the evening had to hold.
When the doors parted, Tammy guided to the end of the hallway and used the keycard to open the door. Kerry’s palm was sweating just as much as mine. We were both nervous, but excited. We both obviously loved Tammy and would do anything for her. But she wasn’t forcing us to do anything. Kerry and I were looking forward to this new experience just as much as she was.
Tammy led us through the sitting room and directly into the bedroom. She laid down on the bed and invited us to join her. With all of us still fully clothed, Kerry crawled up on one side of Tammy and I got on the other. She gently pulled Kerry toward her and began canlı bahis kissing him, slowly and passionately. While she did that, I sat back on my feet and watched. They kissed for several long seconds and I felt so out of place. Before that kiss ended, Tammy began to unbutton her blouse.
I realized I could be helping, I moved to the end of the bed and removed Tammy’s shoes. After I’d gotten them both off, she reached out for me. I moved back to the head of the bed and just when her kiss ended with Kerry, she pulled me in and began kissing me. It was odd to be kissing her seconds after she had been kissing Kerry. But it was still wonderful.
While Tammy and I kissed, Kerry finished opening her blouse and began working her on her slacks. We switched again and while she and Kerry kissed, I worked her slacks and panties down and off. After peeling her giant panties away from her pussy, the scent of her arousal filled the air. Tammy then sat up, breaking the kiss with Kerry and removed her blouse and bra. She laid back down, completely naked with stiff nipples, moist pussy and breathing heavily. She bent both knees and spread her legs wide apart.
In a throaty whisper, she began giving us instructions. She had us kneel on either side of her chest, facing each other. Following her instructions, I reached across her naked body and began to remove Kerry’s shirt. At the same time, he did the same to me. Once we were both topless, she told us to quickly strip to our panties. Kerry and I bashfully slid off the bed. While standing on opposites sides, we both removed our shoes, socks and undid our pants. We stood there looking at Tammy and each other. Neither of us willing to strip first.
Tammy finally whispered to both of us, “You boys are so sweet. Okay, you’ll do it together. On the count of three. One… Two… Three!”
Kerry and I both lowered our pants and stood back up. We looked at each other and realized even in panties, we were so much alike. Our little penis’s were poking against the front panel of the satin, bikini panties. And judging from the appearance it was blatantly obvious that our penis’s were very similar in size.
Tammy called us both back onto the bed. We were once again kneeling on opposite sides of her chest, this time wearing only identical panties. Tammy reached up and laid her hands on our lower backs. She applied gentle pressure, guiding Kerry and me toward each other. We were staring into each other’s eyes as we got closer and closer to each other.
We tilted our heads to opposite sides as our eyes drifted closed and our lips met. In that enchanted moment, Kerry and I kissed. It was so perfect. It was a moment none of us will ever forget. His lips were so soft and his tongue slid along with mine as if we were made for each other. Our lips broke apart for a few seconds while we caught our breath and we both giggled before kissing once again. Tammy pulled us both against her soft body until our pantied penis’s were pressed against her soft breasts.
I can’t be sure what Kerry was doing, but I know I was gently humping my very stiff penis against Tammy’s breast. Kerry and I wrapped our arms around each other and kissed even more passionately than before. While we made-out, Tammy writhed around beneath us while fondling our pantied behinds.
When our kiss broke for the second time, Tammy told us she was tired of being ignored. She gently guided us both down between her spread thighs. We soon found ourselves laying side-by-side, cheek-to-cheek between her thighs. Kerry and I kissed, licked and sucked on Tammy’s meaty pussy lips and clit. From time-to-time, when our mouths got close together, we’d kiss each other and then go back to work on Tammy.
Kerry and I worked so well together. While he focused on Tammy’s big clit, I licked up and down along her fat lips. We’d then switch and I’d take her clit in my mouth and Kerry focused on her lips. We repeated this process several times before hearing Tammy moan. Until that moment, neither Kerry or I had ever gotten her aroused enough to moan! We both froze for a second and looked at each other before going back to her pussy with more enthusiasm than before.
Tammy pushed her pussy up toward our faces and groaned, “My sweet, sweet boys, I love you both so much.”
Kerry and I responded in unison, “We love you too Tammy.”
Kerry sucked Tammy’s big clit into his mouth and began tickling it with his tongue. I turned my head sideways and began poking my tongue in and out of her pussy. It was a little uncomfortable and I rotated my body toward Kerry. While I did that, Kerry turned his body toward me. We were soon grinding our panty-covered penis’s against each other.
Tammy either felt or saw what we were doing and she moaned loudly and began humping her pussy against our faces. Kerry and I licked and sucked and kissed for all we were worth. I wound up sliding up and licking her clit at the same time Kerry did. Having two tongues tickling her clit proved to be enough to make Tammy cum. Kerry and I witnessed her orgasm for the very first time. Until that moment, neither of us had made her cum before. She came hard and her whole body jiggled and shook as the orgasm washed through her.
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