Aislin

1. Virginity

It was happenstance, really. I was a 24 year old IT person, and was at a company dinner to celebrate its fifth year. There were several large tables, and the dinner was a catered party. Sitting across from me was Glenda, a pleasant, matronly woman who worked in payroll, whom I had occasion to help with IT problems now and then.

Seated next to Glenda was a petite, shy young woman who hardly ever looked up to make eye contact. I had never seen her before and wondered if she was Glenda's guest. The young lady had long black hair, was slender, and otherwise ordinary looking. She definitely did not dress to be noticed; she wore a shirt (blouse?) and dark slacks. Probably small breasts.

A discreet look at her hands showed no rings. Why was I interested in her? She was definitely attractive to me, not in a showy manner, though, and I was sure that she was not aware of her attractiveness.

Glenda and I said hello, and as the dinner was winding down, she asked me if I brought anyone. I told her I had not. Then she said, "Rick, I'd like you to meet my friend Aislin."

Aislin blushed slightly, smiled, and extended her hand. I grasped her hand and mumbled something about "nice to meet you."

Glenda then said, "It's kind of noisy in here. We're going to get some coffee at Denny's. Would you like to join us?"

I immediately accepted, and we said our goodbyes to our hosts. Twenty minutes later we were in a quiet booth being served coffee.

Glenda asked, "So, Rick, are you married?"

I suspected where this was heading, and frankly, I was glad for that. "No," I answered, "I've had a few serious relationships, and some casual ones, but now I'm not even seeing anyone. I figure the right person will come along when it's meant to happen." I paused for a moment, then asked, "How did you and Aislin meet?"

"She's a graphic designer where my husband works. He didn't want to come to the dinner, so I asked Aislin."

"Oh... Aislin, are you married or seeing anyone?"

"Umm, no, not seeing anyone either. I have a lot of friends, but no one close."

She blushed again. I smiled. I could see that she was going to be a challenge to draw out, but it was so cute when she did that.

Glenda gave me a knowing smile. The three of us (mostly Glenda and I) chatted about various things, and then she said it was time to go.

I was about to ask Aislin if I could call her, but Glenda appeared to be in a hurry to get away. This was becoming mysterious. Quickly, Glenda said, "Rick, why don't we have lunch soon? There are some things I'd like to talk about."

"Okay... Aislin, I enjoyed meeting you and hope we can talk again."

She smiled and extended her hand. I took it and in a forward (for me) move, gently kissed it before I released it. I had to give ser SOME sign that I was interested.

I had difficulty getting to sleep that night, wondering about Glenda's seemingly overprotective ways with Aislin. Finally, I resolved that I would talk with Glenda the next day and try to get to the bottom of the situation.

At work, I set up a lunch appointment with Glenda. I had to wait until Thursday for our schedules to allow it.

We met at a Chili's and when we were seated, I asked, "It's about Aislin, isn't it?"

"Yes, it is. What did you think of her?"

"She's very quiet... and very attractive. I can't believe she doesn't have a long line of guys asking her out."

"Do you like her?"

"Of course I do. Where is this going?"

Glenda smiled. "She likes you too. A lot. But she's afraid of getting involved in a relationship."

My disappointment must have shown.

She continued, "She's been emotionally hurt at the start of some potential relationships. But as I said, she does like you."

"I'd like to get to know her better," I said. "But I don't know how to make contact except through you."

She laughed and reached into her purse. "Bingo. Here's her contact info, with home phone."

Glenda's expression became more serious. "I could see that there was some chemistry between you two. I think that's a very good thing, and I hope it lasts. I don't know you very well, but I can see that you aren't a rigid and inflexible person."

I wondered what she meant.

She continued, "There are some things that I know about her that I won't disclose. She has to be the one to do that. Just be kind to her."

"This is really getting mysterious, Glenda. But I have no intention of hurting her. I do want to give her a call, and I plan to do that after work."

"Good."

I liked Glenda's directness. It cut through a lot of unnecessary dancing around a subject. Anyway, we went back to work.

The afternoon passed slowly. I had Aislin on my mind, and also the mystery surrounding her. I finally got home, had some leftovers for dinner, and worked up the courage to call her.

"Hello?"

"Hello, is this Aislin?"

"Yes."

"Hi, it's Rick. We met at the dinner where you and Glenda were."

"Of course I remember."

"Uh, Aislin, I'd like to get to know you. Are you free for dinner Friday or Saturday?"

"Oh, I'd like that!"

She sounded happy, but a little worried at the same time.

We decided on Friday, and gave me her address. I suggested a casual Italian place.

A few long days with her on my mind, and I finally went to her place at 6:00 PM that Friday. When she answered the door I got a big surprise. She wore a lovely print dress that settled above her knees, smooth bare legs, and tasteful heels.

"Aislin... you're stunning!" I felt foolish saying that, but I had to say something.

She giggled, "Thank you!"

She said she was ready to go, and we got in my car. I don't make small talk easily, so I didn't say much. She definitely turned a few heads when we were escorted to our table. I could scarcely keep my eyes off her when we were seated.

I asked Aislin to tell me about herself. She said she was 21 years old, the youngest of 2 kids, had an older brother, liked her job as a graphics designer, and that she had a good relationship with her parents.

Then she added, "Also... I'm a virgin."

"Oh wow!" I said. Well, that was better than asking, "Oh really?" Not much better, but a little better. I wasn't not sure why she told me that, but she seemed amused at my reaction.

"Does that bother you?" she asked.

"No-o, not really. How do you feel about it?"

"It just means that I haven't found the right person yet."

Hmmm. So she's particular. That's not so bad, is it? I decided to throw a curve, and teasingly asked, "Am I being considered as a candidate for the job as the right person?"

She couldn't help giggling, and said, "Could be... There's more that I haven't told you, we'll see how you feel about your candidacy after I tell you."

"Okay, I'm listening."

"Not here. Now tell me about yourself."

Fair enough. It's a common complaint that guys tend to talk about themselves to excess and I wanted to avoid that. But I had told her almost nothing about myself so far, so I went through a condensed recap of my life. Thankfully it didn't consume a lot f time. The important things were that I had some casual relationships and two serious ones.

Toward the end of dinner she said, "When you take me home can you come in for coffee and we can continue our earlier conversation?"

She must have been taking "directness" lessons from Glenda. I smiled and said yes. She seemed somber on the way to her place. I wondered if the mystery would be solved that evening.

Without a word she fixed coffee and we silently sipped as she took some time to decide what she was going to say. I was curious, of course, but was not going to force the issue - yet.

Then she sat next to me on her sofa, and then began to cry. I put my arm around her shoulder and let her cry her tension away.

"I like you a lot, and that's why this is so hard for me," she sniffled. "Okay, here goes."

She looked in my eyes, then away. "I was born a boy. I should have been born a girl, and I had a very rough time trying to be what I wasn't meant to be. So when I was eighteen I began treatments. My parents helped a lot and took care of legally getting records changed. I haven't taken the final step, so... I still have... male equipment, and it's functional. But mentally, emotionally, and almost all ways physically I'm a woman. I don't blame you if you don't want to see me anymore, but I just couldn't let things go further without you knowing."

I was quiet for a moment. That was a lot of new stuff thrown at me. I knew that I had to make some quick decisions. Ever since I had met Aislin I liked her - a lot. My head was telling me that I couldn't have an intimate relationship with someone who was born a male. But my heart was telling me how much I liked her. Right then I made a quick decision to go with my heart.

I took hold of her hand and said, "Aislin - you're very brave. It took a lot of courage for you to tell me that, and it was the right thing to do."

She had a sad, wistful smile and answered, "So, it's over?"

I said, "You know I like you a lot, don't you?"

A tear trickled down her cheek and she said, "I hope so."

I pulled her to me and kissed her. Hard. All her stored up passion broke loose and she threw her arms around me and aggressively kissed back. I reclined on my back and she got on top of me and we continued to aggressively make out. Her kisses were sweet, I couldn't get enough.

Several minutes of this, and we came up for air.

"I want you to take my virginity," she said. "If you want to, that is."

At that point, I wanted to be with her. "I do want to," I replied.

"Can you hold off for two more days?" she asked. "I want you to be sure you want to do this."

I looked into her sincere eyes and said, "If that's what you want, I can wait. I know I won't change my mind."

"Hold me now," she said.

She leaned against me and I held her close. She sighed, a long, contented sigh. I realized I was aroused and stone hard. It would not be easy to wait the two days, especially after being offered her virginity. After a few minutes, she noticed my condition, put her hand on the outside of my pants, felt my hardness, and giggled.

"Careful," I warned. "It wouldn't take much to get me to shoot off right now."

She giggled again. "Same with me. I'm so hot I can hardly stand it. We'd better quit now."

"Yeah," I whispered. I didn't want to quit, but it was her body, and I was determined to be patient and see where it would lead.

Then she outlined her plan. I would come over on Sunday afternoon. She would have music softly playing, and we'd go to her bed. Then we'd get undressed and she would give herself to me. For her part, she would get squeaky clean, inside and out. "You can do the same, if you want to reciprocate," she said. Then we would celebrate by going out to dinner. I agreed.

I couldn't resist giving her a hard, passionate kiss before I left.

I had a lot to think about in the intervening two days. I definitely would take what she had offered me, her virginity. I would definitely give her the experience she wanted. And the thought of my being the first one to ejaculate inside her made me painfully hard and almost unable to resist taking matters in my own hand. But I held off.

I wondered what I'd do to reciprocate her pleasure. Did it really matter that much that she had a cock instead of a pussy? What would she expect me to do? How would I feel handling her tool? Should I give her a hand job? I was curious to see her ejaculate. What about taking her in my mouth? Could I do that? The idea of doing that with a guy, repulsed me. But this was her. Aislin. The shy girl I met. I knew I'd want to give her pleasure, I just didn't know how exactly, or how I'd react.

Damn, I was thinking too much. What I had to tell myself was, Go with your heart. Do what you really WANT to do.

I thought about calling her, but I didn't want her to assume I'd be calling to cancel. I didn't want her to cancel, either, so I resolved not to call. I'd just show up.

I'd bring flowers. What flowers are appropriate for a deflowering? Hmmm. A dozen red roses would have to do. I went out and got them on Saturday since most flower shops are closed on Sunday.

All my questions ricocheted in my head until Sunday morning. I also wondered how Aislin was feeling, what she was thinking. I guessed I'd find out.

I did get "squeaky clean inside and out" as she said she was going to, just so I could cover all the bases and not have any regrets about not having done something.

So, with a dozen red roses in hand, I was at her place in early afternoon. She answered the door with an excited smile on her face. She thanked me for the flowers and put them in a vase.

"Well, are you nervous?" she asked.

"Some," I said. "You?"

"Of course. This is a big day for me. Why are you nervous?"

"I'm afraid I'll shoot off right away."

She giggled. "Oh, how sexy! That means you want me! Don't worry, if you cum right away, you'll just have to do it again!"

My boner was rock hard and she knew it. Without a word she put her arms around me. I of course hugged her too, and we kissed. Our kisses became more passionate. Then she broke away and whispered, "It's time to go to the bedroom."

My heart raced as I followed her to her bed.

"Let's get undressed," she said, and began to remove her clothes. I did the same.

I stood there for a moment, looking at her lovely form. Wavy black hair, small firm breasts, smooth slender legs, and a very erect cock. About six inches. Her entire body was a gorgeous work of art, finely sculpted by the universe. Everything about her was exquisitely feminine - except for, you know.

My boner stuck out too. Aroused, hard, throbbing - and ready. I felt her gaze zoom in on my midsection. For an instant she had a look of concern, then acceptance, and then eagerness.

"Let's get on the bed," she whispered. She lay face up, and I got next to her. There was a bottle of high quality lubricant on the nightstand. I ran my hands over her chest, feeling her firm breasts. Then I gently kissed her nipples; first one, then the other. She moaned. Then I kissed her lips. She returned my kisses with a combination of eagerness and restraint.

After a few moments of kisses she whispered, "I'd love to handle you, but I don't want you to cum before you put it inside me."

She kissed me again and said, "I will now give myself to you."

Then she put a firm cushion on the bed and draped a towel over it. She handed me the bottle of lubricant and said, "Use it generously and go slow." Then she lay on top of the cushion face down in a surrendering position. I had never seen a more gorgeous sight.

She spread her legs as I got myself in position for the "main event". She had a perfectly shaped bottom - firm and smooth. I put some of the slippery substance on her nether portal and gently penetrated her with one finger. She sighed. I gave her some more lubricant, and then liberally applied it to my throbbing tool. If she had been the one to lubricate my cock, I would have spurted the instant I felt her feminine hands touch me.

It was time.

The initial penetration got her to voice a sensuous "Uhhh!" With just the tip of my cock inside her, I kept still for a few moments until she whispered, "Okay." Then very slowly I worked my cock inside her, taking short strokes. There were a few gasps, and an occasional "Uhhh!" Finally I was all the way inside. She was so tight, and it felt so good.

"Are you okay?" I asked.

"Oh, yeah! Oh, I feel so full! Lie on top of me now, and then fuck me."

Where did she learn the things to say that would keep my dick so hard? I got in full body contact with her. Then, slowly at first, I pumped my engorged cock in and out. Her reaction was a constant litany of "Ohhh!" and "Ahhh!" sounds. I smiled at the thought that I was experiencing something that so many women, including married ones, never allow.

I was near the end of my self control. "Aislin - I'm about to cum. Is that okay?"

"Yes! Cum inside me! Make me yours!"

That was all it took. Two thrusts, and I erupted inside her. Spurt after spurt after spurt shot through my cock, in one of the lengthiest orgasms I had experienced.

When it was over I whispered, "Oh God, Aislin!"

"Mmmm, yes! Stay inside me if you can. I want you to fuck me again!"

I had no trouble staying inside her. The sensuality of her body kept me semi-hard until I recovered enough to give her a good fucking. Unlike the previous time, I took long thrusts, taking care not to hurt her. Her throaty groans and gasps were sweet, sensual music. I pulled out once to put more lubricant on, and I went on for about twenty minutes before I powerfully ejaculated inside her.

"Oh my gosh, you did me good!" she exclaimed when I pulled out.

"Are you going to be okay?" I asked.

"Oh yes! I'm going to be sore for a while, but that's what I wanted. It'll be a nice reminder of my giving you my virginity."

"I hope I didn't overdo it."

"I expected to be well-fucked," she giggled.

For me, the moment of truth had come. I wanted to give her pleasure. I maneuvered her on her back, and she was erect. I gently handled her cock, looked at it, lightly felt it. I frequently looked at her face to get clues of how she was feeling. Her hips were trembling, and she was oh, so hard.

I knew it wouldn't take much to make her ejaculate, but as much as I wanted to actually see her spurt, I had a different idea. I wouldn't have done this for anyone but her. I took her in my mouth. I swirled my tongue around her member, and in under thirty seconds she erupted. Her hips went wild, and I kept her in my mouth as I felt the pulsing of her spurts and of her cock.

It was sexy knowing that she was experiencing the same kind of pleasure as I do when I cross the line.

And, because it came from her, the girl who offered me her virginity, I swallowed. Every drop.

It took a few minutes for her to recover, and when she opened her eyes, she bestowed a sensuous, loving smile.

"That felt so good. Have you ever done that before?"

"No, Aislin. Never."

She brought my face to hers and we passionately kissed. I got on top of her so I could feel as much of her body in contact with mine as we made out. She became erect after a few minutes.

"Aislin - would you like to go inside me?"

"Yes! Oh, yes!"

I put the firm pillow under my hips and lay back, face up. "I want to feel your lips on mine when you cum. I'm ready now."

With a sexy smile, she knelt between my knees and lubricated her finger. Then, as she locked her gaze on my eyes, she inserted her index finger all the way. Keeping her eyes locked on mine, she moved her finger around until I felt a zing of pleasure shoot through my body.

She giggled. "I found your prostate."

She lightly ran her finger all around that sweet spot, making me squirm and pant. She continued to tease my prostate for several minutes. I'd never experienced pleasure like that before. All the while her eyes were locked on mine, and she had a teasingly sexy smile on her face. She pulled out a few times to put more lubricant on her fingers and continued to tease my prostate. I wanted her. I wanted her inside me, and she knew it.

After an excruciatingly long time, she giggled and applied a generous serving of lubricant to her cock. Then she spread me apart and put the head of her cock against my entrance. Gently, she pushed until she was just inside.

"Uhhh!" My groans were like hers earlier.

"Are you okay?"

"Yes."

She watched closely as she slowly went further in. When her member made contact with my teased prostate, she knew it. Not yet fully inside me, she took short strokes which continually stimulated my prostate.

"Aislin - that feels good!"

She smiled, and then went in all the way.

"Are you still okay?"