Brooke Opens Up

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Oca 11, 2023 // By:analsex // No Comment

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The end of spring was making its way into Pennsylvania with summer knocking on the door and I got to enjoy the drive from Pittsburgh to Hershey for a work conference. You know the ones where they stress three days of leadership and team building. This year, the company picked a five-star hotel with its beautiful venue, attractions, and small cottages. It was a nice getaway from the bustle of the office.We all arrived on Tuesday in order to start checking in around four in the afternoon. I had pulled my travel bag and laptop computer bag in behind me and stood at the check-in counter. I was waiting for my turn in line when I thought I noticed a familiar face but I couldn’t place it at first. One moment they were there near the entrance and then, they were gone the next. It was only a fleeting glance so I blew it off.After checking in, I took my access key and made my way to my cottage. I opened the door and stepped into a wonderful cottage suite with a fireplace in the living area and a separate bedroom suite decked out with a king-sized bed and a large bathroom suite.I quickly unpacked, hooked up my laptop, checked e-mail, and decided I should head to the bar area to meet up with some of the others. There was a social mixer that specific evening and the conference would begin at eight the following morning.The lounge was beginning to fill with company personnel as well as other guests. One of the main attractions to the lounge was their Whiskey selection. They took pride on having over a hundred whiskies from around the world available for your tasting and pleasure. Well, why not try some today and tonight.I ordered my first drink at the bar and moved to the large overstuffed chairs, finding one open and with a nice view of outside and the main foyer, before setting my drink down on the table in front of me. It was then that I noticed that familiar face again. It came to me. It was familiar because it looked so similar to the son of Susan and Brian Peters, members of our group. I tried to recall his name when it popped into my head, Brooks. I thought he was a high school student and maybe sixteen years old.The Brooks I remembered was of slight build, about one hundred and ten pounds soaking wet, maybe five foot four inches in height, long shoulder length blonde hair usually pulled back behind his ears, tanned skin, blue eyes, and very feminine features. He was wonderfully mannered and mature for his age.But this was a young woman, thick long blonde hair pulled back in a ponytail, dressed in tan khaki pants, a pink and white long sleeve button up blouse, white and pink tennis shoes, and makeup that highlighted her lovely facial features. She stood about the same height as Brooks at about five foot four inches, had an extremely attractive and shapely figure with what looked like pert C cup breasts with cleavage slightly visible from the top three buttons of the blouse being unbuttoned barely revealing a gold chain disappearing into the swell of her breasts.It was the glance and the young lady appeared to recognize me, or someone near me outside of my purview, as she waived and began to walk towards my direction. This wasn’t the young man that babysat for Jerry and Jennifer when Jennifer’s parents were unavailable. I recalled having seen Brooks over the course of the past three years off and on at Jennifer and Jerry’s, at the Peters’ home, and at other functions. This wasn’t him. At least, I didn’t think it was him as I tried not to focus on the swell of the young woman’s breasts as she approached. But, then she spoke to me directly in a soft sweet voice, as she got closer.“Mr. Mason, do you remember me? I know this may be kind of a shock to you, but I’m Brooke, Brooke Peters. My parents are Susan and Brian? I used to babysit for Jennifer and Jerry, at least before I headed off to college.” I was confused as he, or she, reached out to shake my hand.“Don’t worry. I changed my name.” She smiled at me and watched me intently as I smiled back and stood up to reach out to shake her outreached hand. The handshake was not firm, but not too weak. Her hands were soft and small, fitting the petite frame. The smile was warm and quite captivating.I held the hand as I responded, “Ah, Brooks, or Brooke Peters?” I didn’t know what to say at first before I added, “I thought you were still in high school. So, you are in college now?”Brooke held onto my hand and smiled back at me, nodding in the affirmative before responding. “I’m attending Penn State. I’m at the end of my freshman year and getting ready to start taking a couple summer classes. I’m here with a small group of friends this week on a break.”“Brooke, if we are going to get along, you can’t be calling me Mr. Mason, it makes me feel like you are talking to my dad and I don’t see him here in the room. Please call me Tony.”My response made her more at ease as I let go of her hand and I could feel her fingers graze my palm as she let go. “Thank you, Tony. I would like that, very much.”“So, Penn State. What are you studying or have you picked your major yet?” I inquired. “I can’t get over it. I remember you, not quite like this, but babysitting Taylor and Chase when Jennifer’s parents weren’t available.”“I love those kids,” Brooke responded with a smile. “I am studying to be an electrical engineer. I love it. So, what brings you here to Hershey?”“Work conference. One of those şişli escort dreaded team building and leadership workshops. We do them every year.” I motioned to Brooke to have a seat in the overstuffed chair next to me. I sipped my drink and frowned. “I’d offer you a drink but I think, if I remember right, eighteen is still too young in the fine Keystone State.”“Have no worries, Tony, I just turned nineteen and we have our own selections of beer, wine, and alcohol in our rooms. We came prepared. Some of us are heading over to the park tomorrow to check out some of the attractions.”“Now, what would your parents think?” I asked.“They know I’m here. I haven’t been here in a couple of years, so it’s all like new for me, especially without my parents hovering over me. So, are you going to ask me?”I looked at her as she smiled, her legs crossed at the knees, right over left with the right foot bouncing ever so slightly. “Ask you?” I raised my eyebrows as if in a quandary.“Yes. Ask me. Like, Brooke, have you changed over the past year since I’ve seen you last, and what is this new look? This isn’t how I remember you when you were younger.” I noticed a gold ankle bracelet on her left ankle as her pant leg rose up, lying atop her white and pink sneaker.I paused for a moment, looking into her eyes and I smiled. “Well, I guess, since you opened the door, I saw you earlier and thought you were a familiar face but couldn’t quite place where from. Then, when I thought I figured it out, you said your name was Brooke, not Brooks. The look, you look quite attractive, as a young woman, dressed the way you are and with the makeup. So, what does this all mean, if I can be that forward to ask?”“See, now that wasn’t too hard.” She smiled at me and leaned over to continue to speak softly, as to keep the conversation between the two of us as the room filled up with more patrons.“Well, let me say first, I know of my parent’s sexual leanings and such. I know both of my parents are bi. As a matter of fact, I know you are too.” She paused to let her comments sink in and to watch for my response before continuing. “Oh, and so are Jerry, Jennifer, Nick, Holly, Tom and Gloria and the whole group that meets every month and sometimes more. I came here this week because I wanted to explore a little and possibly lose my virginity. You know, gain some experience away from campus and home. So, what do you think?”I was stunned. All I could do was say, “Ahh.” I was trying to process everything I just heard. Here I was, a forty-four-year-old bi male having a conversation with the nineteen-year-old “son” of friends who just told me he knew of my sexual connotations and proclivities, as well as his parents’ and all of our friends as if it were common knowledge. Oh, and, he is now a she?“Oh, and seeing that you still haven’t just come out and asked the most important question, I’ve transitioned.” Again, she paused for effect. Then she smiled, “Completely. I had the surgery last summer and recovered before heading off to school. So, when I said I was looking to lose my virginity, it has a totally different meaning than you might have originally thought or believed.” Now, she watched me for my reaction.“Tony, it’s okay. I’m not going to tell anyone here about your sexual preferences and experiences. It isn’t their business unless you want to tell them. But I thought you should know about me. I love it that you are bi. I have watched you and my dad and mom on their DVDs. In fact, I do believe I am bi too.”She sat forward, placing her left hand on my right thigh. “When I saw you, I thought to myself, ‘Hmmm, I think I may have found someone here that would fit the bill.’ I’ve had fantasies about you for a while, especially after seeing you, my dad, and mom as well as the others on the DVDs. What do you think? We dirty up some sheets while you are here and I get to go back to class all relaxed and no longer a virgin? Besides, if you are as good in bed as I’ve seen and overheard, we may be able to play lots, here and back home. I like the idea of that. And maybe you all will have me in the group. Do you think my parents would like to watch or maybe even join in? What do you think? I’d love to tell my parents you and I fucked and would they like to have me join in as well?”I was floored and aroused at the same time. Brooke ran her hand up my thigh and brushed my cock. I was having a time trying to straighten myself out.“I see you like the idea.” She paused for a moment to let her observation sink in. “Well, like I said, I transitioned completely. You know, all of the hormones, all of the surgeries, and such. I am a complete woman, a nineteen-year-old woman with womanly desires.”I looked at her as she began to lean back and watch my reactions. My mind raced as I tried to comprehend what she told me. “How do you know about the group? I thought your parents were pretty careful.”“Well, I’ve seen the videos at Jerry and Jennifer’s house. Oh, and at my house too. My parents have them like I said. I know Jerry dresses and I’ve seen his and Jennifer’s wardrobes many times. I’ve even dressed in their clothes at times after the kids went to bed and were asleep. I think this helped me realize I was really a female and not a male. By the way, those two have great taste in their erotic wardrobes.”I could see where Brooks, as a guy, would have made a very cute girl, well a şişli escort bayan very beautiful woman as she did here. “Well, you are quite a beautiful young lady. It just took me by surprise.”“Why thank you. That is quite a compliment.” She was blushing.“So, what are you suggesting for this evening?”“Again, finding you here was quite a surprise and quite unexpected. I couldn’t have planned it better. Originally, I was going to dress up as a slutty hottie and come down to the bar later after drinks had been going around and people were feeling pretty good and see if there was anyone I would love to have take my virginity. Now, I think I have my idea of what to do.”“And what is that then?” I sipped my drink slowly.Brooke crossed her legs over the knees again and leaned forward toward me. “I think you should go take a shower, go have dinner with your work teammates and a few drinks at the bar. I will come down to the bar and find you after I’ve primped and gotten ready. My friends will help me out. You see, we are each other’s mutual support group. Oh, and I have this little red dress and red CFMPs I want to try out tonight and I have other outfits a lot more slutty that I want to try out during the week. Let me show you how I look tonight in the more seductive look and not quite slutty. Then after some time out here, we can go back to your room and you can fuck the daylights out of me. Who knows?”I smiled at her and leaned forward sliding up in the chair toward her allowing her hand to come in contact with my knee. “I’ll see you then.”I stood up as she did. Brooke shook my hand ever so lightly, smiled and turned to walk away. As she left, I could see her hips sway and pony tail bounce as she moved with confidence, toward the foyer and out of sight. There were lots of other eyes watching her walk out as well.My mind swirled at what had just happened. It took a few minutes to let it all sink in. I decided I would take Brooke’s advice. Really, it was a no-brainer. I finished my drink, headed to the room, shaved, showered and changed into black silk boxers, loose-fitting black slacks, a vibrant blue polo, and penny loafers. I then headed back to the restaurant and ordered dinner. By eight that evening, I was in the bar waiting to see Brooke dressed. I wasn’t sure what to expect. If she were as pretty and eye-catching as she was in her khakis and blouse, she would have lots of eyes on her this evening.Around eight-fifteen, I glanced at the entryway to the bar and there was a blonde woman, hair down to her shoulders and curled, dressed in a red form-fitting dress covering her lovely ass and ending mid-thigh, showing her curves and beautiful lithe legs, in four-inch red stiletto heels and nude hose, grasping a small red clutch. She turned looking over her shoulder, not nervous, but as if she was searching for someone. It was Brooke.She scanned the bar and her eyes went past me once, then twice. Then I saw the smile. She moved slowly toward the bar, in between the overstuffed chairs and the sofas to where I was standing. Her walk was more of a cat-like strut, with a purpose. Like I thought, almost all eyes were on her, both men and women. She looked so delectable.She walked right up next to me, placed her clutch on the bar and turned to whisper in my ear. I could smell her expensive perfume. I knew the smell. It was Eau de Joy. Her mother wore it. She spun around showing off her legs and figure. “So, what do you think? Do I pass?”“Wow, oh, and oh yes!” I softly spoke back. “My God! You are beautiful.”“I’ll have you know, there isn’t a hair on me with the exception of my head and my eyebrows, and even those have been shaped. As for everything else, electrolysis, completely, and I mean completely smooth. My parents spared no expense helping me transition into who I am before you now.”She wore the same gold chain with a pearl pendant that rested in the swells of her breasts and the same gold ankle bracelet on her left ankle. Her nails were still the same red as her lipstick, but with white French tips. She looked as if she was made for the dress and her legs, well, killer.Brooke spoke softly, “You like?”I was sitting on the stool as she stood there. I slid off the stool and motioned for her to take the seat. She slid up onto the stool, very careful not to show any more of herself than was already exposed. She crossed her legs, showing off her attributes, and tilted her head. She whispered softly, thank you. She reached out to touch my arm and pull me toward her. I leaned down and she softly kissed my ear, sticking her tongue in it lightly.I smiled and glanced at her. “You know, you are becoming quite a tease.”“Oh, I’m not a tease. I thought about this the whole time I was getting ready. I plan to seduce you and take every advantage of what you have to offer. For everyone else here, I’m hard to get. For you, I’m all yours.”“So, what’s your pleasure tonight?” I asked while sipping my drink.“Besides you? Well, please order me a glass of wine, a semi-sweet Riesling, please. And, depending on how long we can stand it, we’ll see what happens after a couple of glasses or so.”I looked at her and smiled. “You aren’t old enough to drink here, besides, wouldn’t you have a conflict with your driver’s license?” I was referring to the “he versus she” issue.“No, I have an ID, silly boy. I’m twenty-two. See?” She handed me her license. mecidiyeköy escort It was she, Brooke Marie Peters, twenty-two years old, her face shot, complete with makeup, lipstick, earrings, and her hair down over her shoulders.“Where did you get this?” I asked her.“At college, with the right connections, you can get anything.”She slid her hand over to my arm and held on and smiled at me coyly.I motioned to the bartender and ordered a half split of a good German Riesling for Brooke. Of course, the bartender asked for her identification and she handed her license over to the young bartender who wasn’t more than twenty-four years old himself. He looked at it and then at her and handed it back before saying “thank you, Miss.” He turned and began to pour her split.I looked at her and asked her, “Is there anything else you are going to surprise me with?”She smiled, “I sure hope so.”We chatted for two hours as we drank our drinks. Our conversations covered college classes, how the family reacted to her change, travel, and Jennifer and Jerry. Eyes in the bar were looking her up and down as well as all over. Such a young pretty lady with a guy that was old enough to be her father.She finished her split as I finished a second whiskey. “Oh Tony, I’m feeling pretty wicked about right now. If we are ready to head to your room, I would love to show you how wicked I feel.”She peered up at me, winking and pursing her lips with a little air kiss. I waived for the bartender to settle the tab. All paid, I turned to Brooke and offered my hand to steady her as she slipped off the barstool. The little red dress slid up her thighs exposing the tops of her stockings and the whites of her thighs as she slid forward. Her stiletto heels clicked the floor as they made contact with the marble. She stood up and smiled as she smoothed out her dress over her hips and down her thighs. She gave her ass a little wiggle and picked up her clutch. “Ready.”I put my arm out for her and she took hold of me and leaned her head against my shoulder. “I do like this.” She smiled. “A girl sure could get used to this. A gentleman, not some smart ass college boy who’s only thought is to cum and play video games.”As we walked across the room to the doorway leading through the foyer, I could feel the eyes on Brooke’s ass and killer legs as she swung her hips slightly and clicked along on the marble floor. When she walked on the carpet, I could feel her body push against me, in a more confident walk.As we entered the foyer and out of sight of the lounge patrons, I asked her where she learned how to act so feminine?“Well,” she responded, “I think I have always known I was a girl and not a guy. First, I loved everything feminine growing up. I loved gymnastics; I’m small for my age and was small in the male appendage department as well. I used to get excited helping my mother with “women things” and never was interested in the normal guy stuff. I loved dolls and still do. And, really, I’ve only desired a man although having a woman is also on my mind as oral sex. What do you think, Jennifer, my mom? I think I would really love to go down on a beautiful pussy and feel it cum. That’s why I was so frustrated and knowing I should have been a woman with breasts, a pussy, and this fine ass, as an attribute. So, I watched mom and paid close attention to her. Jennifer is also one of those I’ve paid such close attention to in most every detail I could.”We were almost to the outside entrance as she went on. “I spent hours watching mom get ready to go out and prepare for your little parties. She’d have a friend over, girls and guys, when dad was at work and he would too, for that matter, when mom was out. Sometimes, after they thought I was out, someone or couples from the group would drop by and not leave until the wee hours of the morning. But, as for mom, well, I watched her get ready, so feminine. I could spend every minute watching her get ready, selecting her attire and lingerie, putting on her makeup, and primping before heading out. When I’d hear her moan while she was having sex, I wished it were I and not she. Hey, wait a minute, aren’t we going upstairs to your room? The elevators are over there.”We had walked through the foyer and I guided her through the sliding doors to the outer walkway towards the cottages. “I have a cottage, not one of the rooms. I hope that’s ok.”“Oh my. My knees are wobbly. How nice. I’ve only seen pictures of them online on their website. Are they as nice as the pictures?”“You get to tell me when we get there.” Our walk was fairly short as the clicking of her heels on the sidewalk sounded through the night air.At the door, I fished for the room pass key. Brooke slid in between the door and myself, facing me, looking up into my eyes. “Tony, please, kiss me! I’ve been waiting for this moment and I find it so sexy to kiss you right here, in front of the door.”I put the key into the lock and stopped what I was doing. I wrapped my arms around her tiny waist and pulled her tight to my body, allowing her to feel my throbbing cock against her stomach. She pressed in against me. I tilted my head down as she tilted hers up, looked me in the eyes before closing them anticipating the kiss. As our lips met, I felt her sigh slightly, her lips parting allowing my tongue to enter her luscious lips and find her waiting tongue.It was a very, very erotic kiss. I pulled back to look at her face, her eyes still closed. As they slowly opened to focus on me, Brooke sighed and responded. “Oh my God, that was incredible! I’m tingling all over.” Her breathing was shallow and trembling slightly.

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