The Class Reunion

By pornoperson

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Tags: Transsexual, , anal

Added: 07 Sep 2011 Views: 15373 Avg Score: 4.79

A man finds that his high school girlfriend may have not been all she appeared
In high school I had one girlfriend, Lorena Wright. They were the most frustrating years of my life. More than education, band, music, or hanging out with friends, I wanted to lose my cherry. Alas, my girlfriend suffered from a case of Catholicism.

Sure, we fooled around but it was always with our clothes on. I wanted to know the mechanics of a girl. I wanted to know what a pussy looked, smelled, and tasted like. Her pussy, specifically. But that was not to be. She gave me a couple of hand jobs and she'd get herself off by rubbing herself against my leg but that was the extent of our intimacy.

I'll admit that I spent a lot of time masturbating while I was seeing Lorena, wondering how things would go if she'd only get past her Catholic guilt and give in to me.

Near the end of our senior year, right before I asked her to go to prom, she abruptly broke things off. I tried to find out why but never got a satisfactory issue. This led to a lot of self-doubt and self-image problems over the years.

We traveled in different social circles so once she dumped me I barely saw her again. Soon college and real life took us farther apart until she was merely a memory.

As time wore on, I thought of her less and less until just a few weeks ago when I received an invitation to my twentieth high school reunion. The first thing that hit me as I opened up the envelope and saw my school mascot was, "I wonder if Lorena be there?"

I debated about going but my curiosity got the best of me. I talked a few of my oldest friends into going with me and spent most of the evening talking to them. The more things change, as they say... My friends and I hung out in the back of the hall at our home town's only hotel; making snarky comments about the other people in our class and their significant others. The more things change...

All the while I kept an eye out for Lorena. Occasionally I'd see someone walk in and think, "Is that her?" only to find that it was some guy's spouse.

It wasn't until I had given up hope that Lorena would show that she arrived. I had been up to the bar getting a round for the table. As I came back I saw her standing by the "Memory Table," flipping through an old yearbook. She'd filled out over the years; finally getting some meat on her tiny frame. All of her curves were in the right places. Her breasts looks significantly larger than they'd been. She wore a flowered-print blouse and a dark blue skirt that went with her heels. Her legs looked exquisite.

In school she'd always worn her hair short, almost as short as mine. She'd let it grow out to her shoulders. I couldn't help catch a glimpse of grey at her temples.

She had yet to turn toward my direction. For just a moment I questioned whether I should keep looking at her or turn away. Curiosity got the best of me and I kept on staring.

She turned. Her eyes met mine. And, fortunately, she smiled.

The years had been far kinder to her than to me. If anything, she looked prettier than she did in grade twelve. Her dark features were bright as she continued to smile, coming closer to me. I wrenched my eyes from hers for a fleeting glance at her left hand. There was no ring. My left hand had been bereft of my old wedding band for three years. I unconsciously touched where it used to be.

She closed the last bit of distance between us quickly, opening her arms and hugging me with a loud, "Louis!"

I still held the drinks in my hands and did my best not to spill them as she held me tightly. She put her mouth close to my year and whispered, "I missed you."

She stepped back and asked, "Is one of those for me?" Dumbfounded, it took me more than a beat to realize what she had asked and what it meant.

I gave her a glass saying, "Of course!" I was still stunned, taking her in. It was a ridiculous thought but it came through my head anyway, "I wonder if she's still a virgin." I dismissed this immediately as I knew she had gotten a boyfriend right after she had dumped me. I'm sure all my wheedling had softened her up for the next guy.

I gave my friend his drink and walked away, grabbing another table where Lorena and I could catch up. We exchanged pleasantries, asking out each others' parents, her sisters, and so on. As always, I was captivated by her husky voice. I went from her lovely grey eyes to her full mouth, her slender throat; enjoying the memory of kissing, sucking, and biting on her neck until she squealed. I got lost in my reverie and realize that she had stopped talking. I looked back up at her face to see the quizzical expression there and felt my face flush with embarrassment.

"Well?" She asked. "What do you think?"

"Sure," I stammered, unsure of what the question might have been.

"Good," she said, getting up, grabbing her purse, and starting to walk away. Not knowing what to do, I followed her. She turned and looked crossly at me, "I thought you were going to wait fifteen minutes," she said, a question in her voice.

"Oh, yes, sure." Then, hoping I knew what was going on, I asked, "What room, again?"

"Always the same Louis," she said laughing. "315. Should I write it on your arm?"

"No, no, that's fine. I'll knock on your door in 15 minutes."

She nodded and continued on her way.

In a panic I sat down, checked the time on my phone, and wracked my brain, trying to figure out what she had said to me while I was enraptured by her. All I knew for sure is that I had... eight... more minutes until I went upstairs, to Lorena's room. I had hopes for what might happen but wasn't going to count on anything. Even as we chatted about inane topics she had a slight hesitancy in her voice that indicated she had something more to tell me.

I began doing arithmetic in my head, estimating how long it would take me to walk to the elevator, wait for its arrival, the ride, and the walk to her door. Three minutes? Two? I looked at my phone again. Could I stand to wait another three minutes before I left?

In this position I felt like I often do... like someone's told me the punch line to a joke and I've got to figure out the rest. I try to pay attention but I get wrapped up in little thing. It also doesn't help that I'm often so naive that I could hide my own Easter eggs.

And with that I stood up and left the dwindling group of alumni.

Lorena opened the door. The lights were on behind her, making her a lovely silhouette in front of me. She wore the same outfit as before and I remind myself that it's only been ten minutes since I last saw her. She had enough time to fill the ice bucket and put a bottle of bubbly on it. Two glasses--real glass!--sit next to it. That made me realize that she had this planned all along.

She invited me in. Like any mid-range room there's one chair and the bed to sit on. She sat on the chair, leaving me no place other than the bed. As soon as she sat down she got back up again offering me a glass of champagne.

Working the cork she said, "I'm so glad you came. I was worried. I didn't know if you'd still be mad at me for the way things went down all those years ago."

"All is forgiven and nearly forgotten," I lied.

She sighed with relief but her face still bore her anxiety. She took a drink, a gulp really, as if to calm her nerves. She cleared her throat and said, "I feel I owe you an explanation."

She sat back down, not on the chair but next to me on the bed. I wasn't not interested in her explanation. I'm more interested in picking up twenty some years before. She's about to speak but I don't let her. I lean in and kiss her. She returns it with ferocity. She sighs again, wrapping an arm around me. I felt her tongue snake into my mouth. I was reacquainted with her flavor and it took me back.

We kissed long and hard, the years rushing back to us.

Finally she let out an exclamation and I wondered if she spilled her drink. She put a hand to my shoulder and pushed me back. "No, wait," she said, gasping for breath. "We can't do this; not this way."

That old familiar frustrated feeling washed over me. She must have seen it in my eyes and quickly added, "We need to talk first, then maybe... if you still want to." She trailed off.

"What is it, Lorena? What's the matter?" I tried to sound concerned rather than angry.

"I have to tell you why I broke it off with you." She braced herself with another gulp and sat staring ahead of her as if seeing something in the distance. "I didn't think it was fair doing what I did, leading you on. I... I'm just not... I'm not built like other women," she said, her voice catching.

"You mean... you're a lesbian?" I asked timidly.

She burst out laughing.

"No, no, I'm not a lesbian," she said, wiping tears from the corners of her eyes. "It's just that... well..." she trailed off, turning back to face me. "I never meant to hurt you, Louis. I was just scared that you might not accept who I am, who I really am and I--"

I cut her off with another kiss. I moved a hand to her blouse, unbuttoning it until I could reach in and cup a breast. Of the few things I was allowed to do to Lorena when we were young, touching her breasts and playing with her little nipples were among them. She moaned as my fingers found her nipple. She didn't fight to tell me anything again. Instead, she began leaning to the side so she could lie on the bed.

We broke our kiss. I looked down at her and I began undoing her blouse completely. She smiled up at me as I peeled back the flaps of fabric to expose her flat stomach which was now covered with a huge tattoo; a butterfly with wings that underscored her breasts. The tattoo was new but the silver cross that lay between her breasts. I smiled inwardly when I saw it. The letters "INRI" embossed on the surface reminded me of something I wrote in my journal years before, "I Need Real Intercourse."

The style of bra was the same as she'd worn when we were in high school with a clasp between the cups. I undid it and sank down to kiss her breasts.

This time I really hoped we'd go farther. I reached down and found her legs, touching them lightly, stroking along her skin. As I reached the hem of her dress she put a hand over mine. I looked up at her. She was scared.

"You're not a virgin, still, are you?" I asked, a little incredulous.

"No... God, no. It's not that. I just...."

And for some reason I immediately thought, "Maybe she's not as 'fresh' as she'd like to be. Should I offer to let her go take a shower? What if it's not that at all?"

Before the flood of possibilities could flow much longer she whispered, "Just don't hate me."

"I may have hated you, a little, after you broke my heart but I'm done hating you," I told her.

"You don't understand," she said, "I broke it off because I was scared. I'd never felt that way about another guy."

"Wow," I said, taken aback.

"No, no, it's not like that. I mean, it was but... Oh, Hell!" she said as she grabbed the hem of her skirt and yanked it up. I looked down, seeing her black cotton panties.

I'm a little ashamed to say that it took longer than it should have for me to realize that something was amiss. She didn't say anything but I could tell she was waiting for an answer. I just didn't know what the question was until I finally realized that the front of her underwear weren't smooth. There was no gentle swell of her mons. Instead, I saw the clear outline of an erection. And, again, I felt like I had been living in a world where information... important information... was being kept from me.

My first girlfriend wasn't a girl at all. Or, she was some kind of different girl. I looked up at her and saw the fear on her face. Things suddenly became clearer to me. I knew why she'd never let me get into her pants. I knew why she'd left me before I could ask her to the prom. So many things fell into place; stuff that had always left me a little uneasy now made sense.

Yet, there was still a question that hung in the air. Was this over now that I finally got everything? I won't say there was an elephant in the room but there was definitely something ponderous between us.

I kept my eyes locked onto hers and the decision seemed to be made for me. I remembered all the good times we'd had -- not just the fooling around but the Saturday afternoons we spent at the art museum, the hours we studied together in the library, the miles we marched in band. She was still the same Lorena that I'd always lusted after.

She gasped as I pulled down her panties and she felt my fingers wrap around her cock. I'll admit, I was a little taken aback when I estimated that it was about the same size and girth as my own but I didn't care. I suddenly realized that I could do this. I could make love to Lorena no matter what equipment she had. And, in fact, it might be a little easier to know how to please her since we had the same gear.

I slowly started to stroke her. I'd never touched a cock apart from my own and it was a little surreal to do so. "And here I didn't think you wanted to get pregnant," I said, laughing at myself.

I was finally getting into Lorena's pants and not entirely sure what to do. I always wanted to make her feel good and always loved when she would have her orgasms against me. And now I could finally begin to understand how to please her body even though I never expected it to be this way.

Stroking her a little harder I asked, "Is this all right?"

"It's fine, yes. But... would you kiss me there?" And suddenly we were back in high school. That was the same question I had asked Lorena twenty some years before. She didn't do it for me but I was going to do it for her.

I moved down on the bed to come face to face with her cock. I looked at the way it curved to the right and the other ways it differed from mine. The shaft was thicker and led up to a head that was compact and smallish. I played with her cock the way I like mine touched, stroking my fingers along the underside.

She smelled of perfume and musk. I looked from her cock up to her face, still trying to reconcile my situation. She looked down at me, pleading with her eyes. I knew the want that was there, I'd felt it, too.

I brought her cock to my mouth, kissing it gently a few times before putting the head of it into my mouth. I was surprised by the taste or, more accurately, the lack thereof. I'm not sure what I expected but I guess I was thinking it'd be sour or something nasty. Instead, it was neutral. I slid more into my mouth, keeping my eyes on her face to see her eyes roll back into her head and her mouth go slack.

I noticed two red lines on the undersides of her breasts and it came to me why her boobs looked so much larger than they once had.

I felt her pulse under my tongue as I slid it along the underside of her cock. The irony that I was doing to her what I always wanted her to do to me hadn't escaped me. As I sucked her cock all the times that she had moved my hand away from her crotch came back to me. I also remembered how giggly her sisters and surprised her parents were when Lorena introduced me to them.

I took her deeper into my mouth, sucking her harder, wanting to make her feel good. I heard her begin to moan. "Damn," she said, "that feels so good. You do that so well."

I wasn't sure just how I felt about being so good at sucking cock but I did feel happy to make Lorena feel good. I thought back on all the times that we had rolled around on the shag carpet in my parents' basement, hoping that one day she would take down her pants and let me please her... I just pictured it being different in at least one big way.

Thinking that Lorena had been wholly a victim of Catholicism, I was a little obsessed at making her feel good as if I could lead her into temptation through physical sensation. I spent many afternoons at our public library going through books like "Our Bodies, Ourselves" or "The Joy of Sex," learning as much as I could about female anatomy and orgasm. Years later when I finally started going out with women open to sex I became something of a cunnilingus devotee. I'd spent all those many hours between the legs of many women with the dream of maybe someday going back to Lorena and blowing her mind. As I sucked her cock I couldn't help but laugh at myself.

She moaned louder and longer, a hand moving to the back of my head to push me farther onto her erection. I felt her hips moving up and down in time with the way I bobbed my head onto her. I had a hand on her balls, feeling them tightening as her breath got shorter.

Suddenly her hand on my head tapped me on the shoulder and she began to pull out of my mouth. "No, wait..." she said, breathing hard. I looked up at her as she scooted back, moving away from me.

"You don't know how many times I dreamed about this," she said. "I want to do what I did in my dream... Do you trust me?"

I nodded.

"Good... come up here on the bed." I moved up next to her. We kissed again and she began unbuttoning my shirt. When she was done she mumbled, "Help me out."

I stood up next to the bed and took off the rest of my clothes while she stood on the other side and did the same. We met back on the bed where she directed me to lay on my back. She moved down between my legs and I expected her to lean down and suck me the way I had sucked her. Instead, she positioned herself between my legs while she was still on her knees. She spit into her hand and rubbed her palm along her erection. Her hand still wet she moved it to my cock while she scooted closer to me.

Again, I don't know why I couldn't figure out what she was doing but it seems embarrassingly obvious in retrospect. She began stroking me slowly and skillfully. I looked up at her face which was screwed up in concentration. Suddenly I felt something brush against my asshole. And then the brush became a push. Instinctively I lifted my legs a bit. She looked up to my face and smiled as I felt the push become a little painful. I whimpered a little bit and she shushed me, "It's okay."

The pain increased until I knew that she was in me and it lessened a bit. She began moving her hips back and forth, getting deeper inside of me with each push. She smiled as she looked down at me. "When we broke up before prom, this is why," she said, "I wanted to fuck you that night and I don't think you could have handled it."

"I'm not sure if I'm handling this now," I said, feeling the pain morphing more into pleasure.

"You're doing fine," she said, leaning farther over me to kiss me. She started fucking me harder and faster. I felt her go far inside of me, hitting some kind of sweet spot where everything felt wonderful. I wrapped my arms around her, feeling the muscles in her back as she continued to pound me.

She moved back more onto her knees, taking one of my hands and putting it on my cock. I began stroking in time with her thrusts. She watched me masturbate, her hands going up to her breasts to pinch her nipples. She fucked me harder. I felt like there was nothing else in the world apart from the sensation of her cock buried inside me.

I was getting near the edge and I felt she was too. We breathed hard, both of us panting, both of us sweating.

Lorena pulled her cock out of me. I couldn't believe how much I missed the feeling of her inside me. She moved my hand aside and laid her cock next to mine, wrapping her hand around both and stroking us together. The sensation was overwhelming. Before I knew it, I started to cum. I felt my hot spunk shooting out of my cock and I felt more, I felt her own also landing on my belly. I looked down, seeing her hand coated in a mix of our mess.

She collapsed down next to me. I put my hand below her breasts, feeling the rise and fall as she worked to catch her breath. She looked over and smiled at me.

And so it had finally happened. Lorena and I finally had sex, though not in any way that I had ever thought about before.

We both visited the room's tiny bathroom to clean up before we fell into bed together, still undressed. I found myself wrapped up in her arms and fell asleep to her breathing. In the morning we made love a second time; slower than the first but with no less intensity. I found that I was hungry to suck her cock a second time and knew that I would remain so.

I didn't regret the time we had been apart. After twenty years we were finally ready to be together.