Her First Chance at Love

"I have a week's vacation coming up," I told my Aunt Sheila, "and I don't know what to do with it. This is the first time in over fifteen years that I can actually afford to go somewhere, and I have no idea what to do or where to go."

"So, why not come and see me?" she asked. "I haven't seen you since Christmas."

"Hmmmm," I said as I thought it over. Yeah, she came down for Christmas, and now here it was August. "You know what? I'll do it."

"Oh, good," she said with a lilt in her voice. She had always called me her favorite nephew, and I, of course, always said she was my favorite aunt. "When should I expect you?"

"How about I leave out Monday morning around seven?" I asked. "That should put me getting there between three and four."

"I'll get us some Ribeyes to throw on the grill," she said.

"Sounds good."

"Call me if anything changes."

"Oh, it won't," I assured her. "I'll be there if I have to hitch-hike."

I finished out my week at work, took the weekend to clean up around the house and mow the lawn, and just as promised, I was North Carolina bound first thing Monday morning.

Sheila lived about the midway point between Dunn and Godwin where she and her husband, Jerry, owned fifty acres of land. After a little over eight hours of travelling East on 84 and North on 95, I arrived at her home, a large manor that had been refurbished inside and out. She came out to greet me as I pulled my luggage from the trunk. She threw her arms around me and said, "Oh, it's so good to see you again."

"It's been too long," I remarked.

"Come on inside," she said as she took possession of my duffle bag. "We have a guest I'd like you to meet."

"Where's Jerry?" I asked as we made our way up the steps.

"Oh, who knows?" she said with a laugh. "Probably out with one floosy or another." I laughed, simply because I knew she didn't mean it. That was just her sense of humor. "Actually, he's in Greensboro on business, but he should be home for dinner."

We entered her house, and in the parlor, I saw the most striking woman I had ever lain my eyes upon. She smiled as Sheila and I approached. "Doug, this is Wendy, your cousin Kim's daughter. Wendy, this is Doug."

I set my suitcase down and took her hand in mine. "Enchanté, mon amour." She began speaking flawless French. I quickly stopped her. "Whoa-whoa-whoa. What I just said and 'Omelette au fromage' is the only French I know."

She laughed, then, in a very sweet voice, said, "It's a pleasure to meet you as well."

I kissed her hand, all the while knowing her truth. This did not impede my mode of thinking, though, as I was completely enamored with her. "Sheila failed to mention she was entertaining such a lovely guest."

"Wendy's been here about three months now," Sheila reported.

"How are you finding your stay?" I asked.

"Sheila and Jerry have been nothing but hospitable," Wendy noted.

"As we will be with you," Sheila said to me. "Now, come on. Let's get you situated in your room." I followed behind her as she led me upstairs and down a hall. She stopped at the last room on the left and said, "Here we go. Wendy sleeps in the room to the right, and Jerry and I stay in the room at the other end."

"Okay," I said. "Just let me empty my suitcase and duffle bag and I'll be down. Got those steaks marinating?"

"Oh, you bet," she said. "Been marinating for two days now." She smacked her lips, then hugged me. "It's so good to have you here, Doug."

"It's good to be here," I responded. Sheila departed, and my mind immediately turned to Wendy. She was a knockout, but how? I wondered this as I put my clothes away.

When I arrived downstairs, the two were drinking wine. "Would you like some?" Wendy asked.

"Yeah. Sure," I responded. She poured a glass and handed it to me. "Thank you."

"You're such a gentleman," she said with a smile as she took her seat. She looked at me, then said, "I really can't remember my mother ever talking about you, other than her cussing up a storm one day because Grandma reminded her of something you once said."

"Oh, it wasn't him," Sheila quickly said in my defense. "We were at a family reunion—this is before you were born, of course—and she said ... What, exactly, was it, Doug?"

"I was there with my girlfriend at the time. Well, actually she was my fiancée. She is black. Anyway, your mother very loudly made a comment about all niggers needing to be shipped back to Africa. I quoted the dictionary definition of nigger, 'Any unclean or uncivilized person,' and told her that since her front yard looked like a rubbish heap and since she was acting in a most uncivilized manner, she was the nigger. Things escalated from there, and my girlfriend and I left. I never spoke to your mother again. For the record, my fiancée and I married and had a little girl. We divorced about five years later."

"I'm sorry," Wendy said. "On both counts."

"It is what it is," I offered as a reply.

"Well, she can be a real bitch at times," Wendy said. "Thus, my reason for being here now."

"And you're welcome as long as you wish to stay," Sheila said.

Not long after, another bottle of wine was opened. As we neared its end, Sheila's phone rang. She put it on speaker phone, then said, "Hey, babe. I was just about to call you. Those steaks can't wait much longer."

"About that," Jerry said. "Looks like I'm going to miss out. Seems I forgot to bring the hard copies of the recalibration files. Could you be a dear and bring them to me?"

"Oh, baby. Sorry, but no can do," Sheila told him. "We've gone through two bottles of wine here since Doug's arrival. I don't dare get on the road."

"And I wouldn't ask you to, knowing this." He sighed. "Well, I can't do anything until tomorrow anyway. No more wine for you tonight and you bring me the files tomorrow, okay?"

"Sure thing. See you around nine?"

"Perfect." They kissed each other over the phone and said their I love yous, then Jerry gave me a shout-out before ending the call.

"Well, those steaks aren't going to cook themselves," I said as I started toward the grill.

"You're a guest," Sheila said to me. "Sit. I'll take care of them."

"Guess I'll go ahead and get my shower," Wendy said, then took her leave.

I mocked Sheila as I filled my wine glass again. She threw mushrooms at me, one of which I caught in my mouth. We talked about little things in between her putting potatoes in the oven and broccoli in the steamer. The steaks would wait until the last minute.

Wendy arrived downstairs wearing a tube top that looked to be a size too small yet showed off her tiny breasts so perfectly and a mini dress that revealed, when she moved too hastily, that she was wearing a thong. She had a trim waist and really sexy legs. It was all I could do to keep from looking at her, and eventually I failed, catching glimpses out of the corners of my eyes every so often as I dared to.

Everything was finished except for the steaks. Luckily, we all liked ours rare to medium rare, so cook time was next to nothing. Wendy and I set the patio table and we sat to enjoy a meal out by the pool. "I'm jumping in that thing tomorrow," I said.

"I was hoping you would want to go to Greensboro with me tomorrow. The both of you."

"Much as I'd like to, I came here to relax," I said to Sheila.

"I suppose that's true," she said.

"And what kind of a hostess would I be if I went with you and left him here all alone?" Wendy asked. Then, answering her own question, "Not a very good one. I'll tell you that much."

"Okay-okay," Sheila said. "I'll stay over and have lunch with Jerry before coming back. That should put me home around four. If things go well, he shouldn't be too far behind me."

"Cool," I said. "Can we eat now?"

We did.

Sheila wouldn't hear of me helping with the dishes. She and Wendy took care of them as I got my shower. I returned to the living room around eight to find the two sitting and talking. Sheila was sitting in a recliner and Wendy on the left side of the couch adjacent to her. They greeted me as I sat on the right side. "Is there anything in particular you'd like to watch?" Wendy asked.

"Have you ever seen Rick and Morty?" I asked.

"Never heard of it," both replied.

"What?" I asked in disbelief. "Seriously?" They nodded. "Do you have hulu?"

"We have a Fire Stick," Sheila said.

"Even better." I had one as well. I went to Morpheus and pulled up the show. We watched about four episodes, and the ladies were in stitches. Sheila finally called herself off, though, citing the need of a shower and sleeping off the wine. Wendy stayed, and we watched three more episodes before she decided to call it a night. "I guess I will as well," I said, and followed her up the stairs. Good night," I said to her as I went to my room. I glanced at the clock before lying down. It was eleven-thirty. Not long after, there was a light tapping at my door. I glanced at the clock to see it was just past midnight as I said, "Yes, come in."

The door opened, and immediately I could tell it was Wendy. "Hi. Can I come in?"

"Yeah, sure," I said as I sat up. I inclined my head to the open spot to my left. "Have a seat."

She did. She said nothing for about thirty seconds, then made the declaration, "I noticed you catching glimpses of me since you arrived."

"I'm sorry if I made you feel uncomfortable," I said in way of an apology. "That wasn't my intention. I just ..."

"What?"

"I just can't keep my eyes off you," I told her. "You are the most strikingly beautiful woman I have ever seen." Even in the dark I could see her smile. I decided to push things a little to see how far she was willing to go. I lifted the sheet and said, "Wouldn't you feel more comfortable under the cover?"

She studied me for all of fifteen seconds, then said, "Before I do, you need to know something. I'm a transgender. Male to female, and Pre-op."

"I know," I told her. Of course, I knew. This was her truth I had eluded to earlier. I may not have spoken to her mother in almost thirty years, but I knew through other family members that Kim had given birth to a son whom she named Oliver, who should be about twenty-eight now, and four years later she gave birth to another son she had named Wendell, thus "Wendy" who now sat before me.

"Did Sheila tell you?"

"No," I said, and explained it to her.

"And you're cool with it?"

"I am if you are." I was still holding the sheet up. "Offer still stands."

She stood and removed her night gown. I could see by her silhouette that not only was she not wearing panties, but she was completely hard. I quickly kicked off my underwear. She got in bed next to me, faced me, then asked, "What now?"

I moved in to kiss her, but then I quickly pulled back. "You know I'm here for just a few days, right? I mean, I don't know what your expectations are, but—"

"Hey, no promises, no demands," she said, then she leaned in and we kissed. My cock went from flaccid to hard as steel in a matter of seconds. I reached between her legs, took her cock into my hand, and began to slowly pump it. It felt every bit as long and big around as my own. She did the same to me as we continued kissing. We stayed like that for about five minutes, then she asked, "Have you ever been with a transgender before?"

"No," I answered honestly.

"Are you nervous?"

"Yeah, a little."

"I'll go first," she said, then eased me onto my back before beginning to kiss her way down my chest. She stopped at my left nipple and flicked it with her tongue before lightly sucking it.

"Harder," I whispered. She did, but not to my satisfaction. "Harder," I said again. "Harder," and then she hit it, that point where pleasure and pain become one. "Oh, fuck yeah." I placed a hand on her head and held her there. My cock throbbed. She continued to suck my nipple a good minute longer, then began her southbound journey once again, then I felt her mouth engulf my cock. I cried out but managed to stifle it so as to not alert Sheila to what was going on in her house.

Wendy did an exemplary job in taking care of me. It took about fifteen minutes, but I came. She allowed me to cum in her mouth, too. I pulled her close and kissed her. She had apparently swallowed, for there was nothing in her mouth as my tongue snaked through it.

"There's no rush," she said to me as she lay on her back. "Just take your time and make love to me with your mouth." I followed her instructions. We kissed, then I made my way to her tiny breasts. Her nipples were so soft in my mouth. It felt really nice.

I licked my way down her belly, then bypassed her cock altogether and began caressing her balls with my tongue. "Ohhhh," she whispered. I felt her scrotum tighten. I ran my lips along the shaft of her cock until I reached the head, then I enveloped it with my lips. "Oh, God yes," she said. I sucked the head alone for about five minutes. I loved the way it felt both soft and firm. I reveled in the way it plopped in and out of my mouth. Finally, though, I began going up and down on it, taking a little more into my mouth and down my throat with each passing. I was surprised to find that I could deep throat her with ease. I continued doing that, and about ten minutes later she announced she was cumming. I moved my mouth to the head and felt every spurt of cum she unloaded into my mouth. It was quite a load, too. I held it in my mouth for several seconds, then swallowed. I then moved up and we kissed. "Oh, you swallowed it?"

"You did," I reminded her. "Wouldn't I be a hypocrite if I didn't?"

"It wouldn't have mattered," she told me. "Not on your first time out; but thank you. It means a lot to me."

We continued to kiss for about five minutes more, then she stood and reached for her nightgown. "Um, you can stay here if you like."

"Better not," she said. She bent, gave me one final kiss, then returned to her room.

I awoke at eight-thirty, which meant I slept through Sheila's departure. Oh, well. I'd see her tonight. I brushed my teeth, washed my face, brushed my hair, dressed, then made my way downstairs. I found Wendy in the kitchen. She was wearing a shirt with the sleeves cut out, and instead of it being buttoned it was tied just below her tiny breasts. Her shorts were denim, and she had cut them to where one could see her ass cheeks. A pair of cowgirl boots completed the ensemble. She looked beautiful.

She spotted me and said, "Cereal, or oatmeal?"

"Oatmeal," I replied.

She fixed me a bowl, then asked, "You want peaches and cream in it?"

"Sure."

I sat at the breakfast bar as she pulled the items from the fridge. She sliced the peaches, added the cream, then set the bowl before me. She fixed herself a bowl of plain oatmeal, then sat next to me. We ate in silence for a few minutes, then she asked, "Would you like to go on a picnic?"

"Sure. Where?"

"There's a clearing about two hundred yards into the woods, A small creek runs through it. It's really nice."

"Sounds like it."

"Good. Let's plan around noonish."

We watched some more Rick and Morty, then at eleven-thirty she went to the kitchen to get things in order for the picnic. I followed a few minutes later and stood beside her. "Yes?"

"May I kiss you?"

"You don't have to ask that," she said with a smile.

I stood behind her, wrapped my arms around her waist, then placed my lips on her neck. She reached back and ran her fingers through my hair. I turned her head and kissed her on the lips. We kissed for about a minute, then she pulled back and said, "Save some for the picnic." I smiled, simply because that meant she was receptive to more.

She packed Italian bread, Swiss cheese, and red wine. As we made our way to the clearing, I said, "May I ask you a question?"

"Feel free to ask me anything you want," she replied.

"Yesterday you said your mom could be a real bitch and that was why you were here," I began. "What happened between the two of you?"

"On my twenty-third birthday I told her I was gay," she said, "but by my twenty-fourth I realized I wasn't gay at all, but wrongly sexed. I always felt I was a woman, I just didn't know how to accept that of myself. I told her this and she flew off the handle. Long story short, I called Sheila and asked if I could come stay with her a few weeks. That was three months ago. She was so accepting of me, of who I really am. She and Jerry both. She's the one who got me started on hormone therapy."

"So, you're wanting to do the whole thing?" I asked. "Sex reassignment surgery?"

"Eventually," she replied, "but I'm not in a rush. It'll happen when it happens."

We had reached our destination. The grass was lush and green while the leaves on the trees were just beginning to change color. The creek gently meandered by, whispering its secrets as it carried them further down the line.

I lay a blanket upon the grass, then we removed our shoes as we sat. A glass of wine for us both, then Wendy said, "May I now ask a question?"

"Anything," I said.

She smiled. "Why aren't you kissing me?"

I gulped down my wine and she did the same. She lay on her side. I moved in close and began to kiss her much the way we kissed last night. "You're a good kisser," I said.

"So are you."

We continued. I loosened her shirt and softly sucked her nipples, giving equal attention to both. I kissed my way to her belly, then removed her shorts. She was wearing a thong, and her cock was aching for release. I pulled the thong to one side and immediately accepted her penis into my mouth as it shot straight up. I gave glorious salutations to it much the way I had last night, and just as I was beginning to wonder if she were going to cum, she did. I milked her dry, then swallowed my intimate treasure.

I pulled my shirt off and unbuttoned my pants. She was on me, straddling my hips. She kissed me, then took my left nipple into her mouth. She quickly found that pleasure / pain place and worked me over even as she pinched my right nipple. She eventually slid down and removed my pants and underwear, then began to slowly caress my cock with her wet, parted lips. I lay there as the birds chirped and the crickets played their esoteric symphonies and the creek continued to quietly babble downstream. I was at one with nature, and I came in her mouth. My cry of rapture was so intense it caused a momentary cease to the animal noises around us, but they began again quickly enough. Wendy moved up to my mouth. We kissed for a few minutes, then we dressed and enjoyed the picnic.

We were back home by three. Sheila called at four to tell us she and Jerry were en route and for us to meet them at Panda Express at six. We had a nice dinner and Jerry and I were able to catch up while Sheila and Wendy talked amongst themselves.

Jerry and Sheila went to a bar afterwards. Wendy and I were invited, but we decided to go home. We watched some more Rick and Morty (we were almost finished with Season two) when Jerry and Sheila stumbled through the door. They were singing "The Life of a Pirate" between bouts of drunken laughter.

"I hope y'all didn't drive home like this," Wendy said to them.

"We took a cab," Jerry sang, then he and Sheila haphazardly made their way up the stairs and to their room.

"Now they're going to have drunken sex before passing out," Wendy said with a snort.

"They do that often?"

"About every other week," she answered.

"Have you ... Um ..."

"What?" she asked. "Heavens, no."

"I'm sorry. I didn't mean to insinuate—"

"It's okay," she said as she entwined her fingers around mine. She looked deeply into my eyes, then asked, "What about you? Ready to go up?"

"Yeah," I answered quietly.

We made our way to my room where we immediately began to strip. Once having done so, we embraced and began to kiss. I really enjoyed kissing her, and a part of me wanted to do just that and nothing more, but another part, my hard cock, wanted something else. She began to slowly masturbate me, then pulled back and asked, "What would you like to do tonight?"