Accidental Date With Tranny

Hi All, This is my first submission and truthfully I have not written a non-technical work in years. I discovered in writing this that my English grammar sucks. I had run-on-sentences in run-on-sentences. Well as long as I don’t write my English teachers I won’t be lynched. I guess I have to relearn writing again.

Anyway, this is an account of the first time I met Terri. She helped me in trying to remember much of our conversations. Much of it unfortunately is a best effort or paraphrased. This happened almost 30 years ago. So two old farts aren’t going to remember conversation detail. I’m just glad we hadn’t forgotten the sex. That would be bad. Anyway, I hope you enjoy. Comments are welcome, help with English grammar is also appreciated.

About 3 years after my divorce (This was over 30 years ago); I decided it was time to get back into dating again. I finished my Masters. I had a good career. And a few good friends who helped me with my sexual desires. But it was time to try getting into a relationship.

Dating online is very hit and miss. I met some really great people and some not so great. Fortunately if you’re smart; you can wade through most of the unwanted ads. One of those dating ads got by me; catching me completely off guard. What happened I never imagined or saw coming.

I received a response from a single white female about my age. She lived within 10 miles of my home. I read her response and thought, “Why the hell not.” I returned her response and we started communicating with each other. After a couple of weeks of emails and eventually IM chats; we finally decided to meet.

We agreed on a nice restaurant we knew in a nearby town. It was Friday evening. It was warm and sunny; not a cloud in the sky.

I drove up to the restaurant and parked . By the time I walked in the sun was just dropping behind the surrounding buildings. I was a little early, so I asked for a both which would afford us some privacy. I took my seat; ordered a beer, and watched the door for her.

About 5 minutes after we were to meet; this attractive woman entered the restaurant. She stood 5 feet 4 inches, great face, and beautiful long blonde hair. I stood up and waved at her. She saw me and immediately walked in my direction. She was wearing jeans, a white blouse, pearls, and high heels. She was really cute, sexy and slender. She did her jeans proud. And though not large; she appeared to have at least C cup breasts. Her blouse was so loose; I couldn’t be sure. I offered her a seat, and sat down across from her. I thought to my self, “Wow, she’s actually very attractive. This is promising.”

I’ve learned long ago how to look at a woman’s eyes; when talking to her. I know her breasts are their, but I’m not supposed to talk to those. While looking at her face; I noticed her neck. The Adams apple was large and protruding. “Oh damn” I thought. Now I’m wondering if she is a guy in girls clothing.

So I tactfully lead the discussion toward a mix of sex and politics. Both areas I have some knowledge in. I’m center right on politics. As for sex? Anything goes so long as it’s consensual; the participants are old enough, and are mentally capable of understanding the consequences of their consent.

Eventually during our conversation; Terri smiled and said “Don, thank you!”

I’m confused. I said “For what.”

Terri said, “I can tell you noticed my Adams Apple. And you’ve sat here very politely working out how to ask me what you don’t want to ask me. Well…, I am a transsexual. I know I’m not what you were looking for in your ad and I’m sorry for deceiving you. It was wrong of me to do so and I am truly sorry for wasting so much of your time. I am also very thankful; you have been so nice about it.”

I stopped her and said, “Terri, actually, I wasn’t sure. Yeah, I was kind of suspicious, and I was leading you toward this discussion. Don’t worry about the time. Really; I would have sat home watching TV if I hadn’t come out to see you. If nothing else I am having a good time.”

Again, she thanked me an said, she should probably leave me in peace.

I said, “Why? Did I do something wrong?”

She said, “No, you’re a great guy. I’m just not what you’re looking for and I don’t want to ruin the rest of your evening. I honestly don’t know why I did this. I guess I’m kind of hard up to meet someone, that’s all. This is a small town.”

I cut her off, and said, “Hey look. Let’s say we end the date thing right here and now, and put it behind us. Unless you have something better to do. I really don’t feel like TV tonight. Do you bowl?”

Terri smiled and said, “Seriously? You’d go bowling with a transsexual?”

I laughed and said, “What Trannies don’t bowl?

Terri laughed and said, “Well, this Trannie bowls.”

I said, Okay. Just do me a favor and act like a girl. You obviously look like one.”

Terri said, “If I get a strike; I’m going to jump up and down and scream. I may even grab you and hug you.”

I started laughing, and said, “The other guys are going to see a cute girl hugging a guy. Only you and I will know the truth. Probably be safer for you anyway.”

Terri smiled and said, “You gotta point. I don’t need a bowling team beating the crap out of me. Okay, you’re on; but I have to tell you. I’m going to kick your ass”

I said, “Oh, you are so on.”

We drove separately to the bowling alley. As I’m driving I’m thinking. “She’s gutsy trying this. I could have beat the shit out of her. I know she’s thinking about it.” We turn down the street the bowling alley is on. “I remember not to long ago. I had a sexual relationship with two guys who were friends and co-workers.” We pull into the bowling alley parking lot. “She said, she’s new in town and doesn’t know anyone. Something tells me she’s lonely and feeling the issues of being a tranny in a small conservative town. I wonder if I should tell her I’m bi.”

Terri got out of her car and knocked on my passenger side window. I let her in, and she sat in the truck with me.

Terri said, “I need you to do me a favor.”

I said, “Okay?”

She said, “You know the truth; I’m a transsexual; this is my life. What ever you do, please refer to me as a woman or girl. Please don’t think of me or talk to me as if I were a guy.
And as a favor. Stare at my ass occasionally and at least pretend you’re enjoying the view. I put a lot of work into sexily filling these jeans. It’ll make me feel better.”

I had to laugh, I told her I had never had a request like that. Then I said, “Okay Terri, step out and give me a spin. Let me see.”

Terri got out and struck a few provocative poses. She spun around a few times to give me a good show. I’m thinking, “Wow, she’s go the ass of a teenage girl. Nice; really nice ass. Her ass is as tight as those jeans. Man oh man. She’s got some really great curves.” Oh man. Now I’m starting to feel a little horny.

I said, “Terri, I would be honored to stare at your ass.”

I heard her laughing as she shut the door.

I got out and we walked in together. I paid for the lanes, but Terri insisted she pay for the shoes. We played three games. I had no problems staring at her ass. Damn if I didn’t enjoy watching her bend over to throw the ball.

When she rolled a strike or a spare, I got up to her jumping up and down and gave her a hug. I hate to admit it, but she did kick my ass, not to badly, she won the first two games. I barely won the third, I think it was by 4 pins. Somewhere during the second game she had to make use of the rest room. On her way back some clown tried to hit on her. She brushed him off, but was a little concerned about something he said to her. She wouldn’t tell me what he said. She only said, he’s showing me a little to much attention.

He was a big guy and Terri just felt like he was trouble. Terri is pretty slender and not built for a brawl with a guy like that. I’m 6 foot 4 inches, 220 pounds, very muscular. I could bench press 350 and though these days it is slowly fading; I have a six-pack. I am a Taekwondo third dan black belt and I’m a pistol marksman with a concealed weapon; former military. I don’t think kicking his ass would have been a problem for me. If he pulled out a weapon; I don’t miss. But these were not my first best options.

I noticed him staring at her and said to Terri, “I see what you mean; let’s put him off. Kiss me.”

Terri, looked at me completely shocked. She smiled and said, “Oh hell. I’d love too.”

We kissed, but no tongue; though she did part her lips a little. I suspect she was waiting for me to slip her my tongue. Just for show, I ran my fingers through her hair and held the kiss for about 10 or 15 seconds. A nice long kiss.

I took a peek and noticed Terri’s clown turned and walked off in some other direction. I guess he figured she’s taken.

We ended the kiss, and I told her the clown took off. He’s no longer zeroed in on you.

Terri said, “Thanks! If he would have found out what I am; he would have mopped the floor with me. Oh, by the way, you’re a great kisser. That was fun.”

I smiled and said, “Thanks Terri, nice to know I still have some talent.”

Terri smiled and slid her hip against me and said, “mmm, I’m sure there’s more.” Then she stopped. It slipped her mind in the heat of the moment that we weren’t a romantic couple. Just two people out bowling. This look of panic came over her face. She told me later she was a little turned on from the kiss.

I bumped her back and put my arm around her. She smiled.

Well, the rest of the bowling went without incident; we had a good time. We walked out and found the clown standing out there. I told Terri it might be best if we leave her car there and she leaves with me. We can come back later and get it.

She saw the clown too and said she’d really appreciate it.

We took off from the bowling ally. Unfortunately its a small town. Everything closes up this late at night.

I said, “Terri, do you trust me?”

She looked at me and said, “Hmmm, I lied to you to meet you, I deceived you into thinking I really was a girl, you take me bowling, and you protected me from a really big guy who probably would have raped me. I don’t deserve your trust, but yeah, I trust you.”

I said, “Let’s go to my place it’s not far; we can hang out awhile and come back later for your car.”

Terri smiled and said, “Sounds great let’s go.”

We got to my place. I let the Rockys out. I have two big German Shepherds. Terri found my refrigerator and grabbed two beers. It cooled down, so we sat out on my back patio. As we settled down we started talking.

She asked where the Rockys went. She couldn’t see a fence in the darkness.

I said, “Oh, somewhere out there; they have a little over 58 acres to roam on. Their probably chasing down a squirrel or rabbit.”

Terri, said, “wow, lots of land to play on.” Then she said, “Don, do you mind if we get personal?”

I said, “What would you like to know?”

Terri said, “Most guys would have walked out or decked me for what I did to you; why didn’t you?”

I said, “First, what good would it have done. I’d be in jail. You’d be in a hospital. There would be no good in that. Okay, so you ready for an explanation?” I think you’ll understand.”

She said, “Oh I’m all ears. This will be good.”

I laughed and said, “OK, Terri, I’m looking for someone for love, I’d prefer a woman and I mean, someone who was born with all the right parts. That does not mean I object to bisexuals or transsexuals. I’m just interested in a heterosexual marriage. Anyway, about two and a half years ago, I was having a pretty rough time with my divorce. We thankfully had no kids, but the ex wanted to fight over every scrap of property. She even tried to claim my underwear. During that time for almost a year I masturbated two and three times a day. I was alone.

I continued, “Well, I had developed a friendship with two guys Bob and Jim. I’ve known them for several years. One day the three of us were sitting at a bar telling jokes and Bob tells me they’re bi. I at first thought the were screwing with me, but they said they really were. At that time I was straight, but I’m a very curious person so I started asking questions. We talked for almost two hours.

Well, at some point, they invited me to join them that night for a threesome. I was hesitant and first and not sure what to say.

Then Jim said, “Hey, you don’t have to do anything. The two of us can show you what we do and if you want, we can give you a blow job.”

At that point, all I’m thinking is, “It’s Friday. I’m fucking lonely and horny as hell. I haven’t had sex in over a year and I was really turned on by the idea of someone giving me a blow job”. So I accepted their invitation.

Well, we got to Bob’s place and they gave me one hell of a show all right. I watched as they 69’d with each other. I couldn’t help but be turned on and I started rubbing myself through my pants. Bob noticed and told me to pace myself. He said, they will be happy to take care of that.

Well, they finished each other; got off the bed and came over to me. Both of them started taking my pants off. They knelt in front of me, Bob had me put my foot up on a bed stand, he then started sucking my balls. Jim was masterly giving me the best deep-throat blow job I’ve had since before I got married. Jim’s lips and tongue sliding up and down my cock was exciting to say the least, compound that with of Bob sucking and licking my balls and Perineum; nearly all the way to my anus. I was absolutely out of my mind. I started thrusting into the Jim’s mouth who continued to deep-throat me. Bob stopped licking long enough to tell me to grab Jim’s head and fuck his mouth as hard as I needed.

I grabbed Jim’s head and started screwing his mouth. Jim just sucked even faster. He grabbed my ass and pumped me faster. All of a sudden I felt a lubricated finger sliding up my ass. I felt another finger pressing just behind my balls. I grunted loudly and I just started shooting buckets of cum down Jim’s throat. As I settled down Bob replaced Jim and milked my cock to the very last drop. My cum was now his.

I ended the story and said to Terri, “So there you have it. Jim, Bob and I for the next year had more nights like that. They taught me how to deep-throat cock.

Terri said, “So where are Jim and Bob now.

I said, “Well as it sometimes happens I took another job; which took me to the other side of the country. I had no kids and no reason to stay there and I needed to live closer to my family.” Terri sat for a few seconds not saying anything but I could tell from the light of the Tiki torches she liked the story; based on the bulge I was looking at in her tight jeans.

Terri, cleared her throat and finally spoke, “Damn it, that was exciting as hell. So now I know why you didn’t deck me. You’re bi. Okay, so you’re out here now. What have you been doing.”

I said, “Well, I have two female sex friends at work and on occasions we get together for a little one-on-one and threesomes. Twice we rented a cabin and one of my friends brought her sister and another friend. My other friend brought her friend. We had a six way with me and 5 women, that my friend was one hell of a night.”

Terri said, “Oowwww stud muffin.”

I laughed and continued, “We also go to movies and dinner together. Going solo is just not that much fun.”

I noticed Terri trying to adjust herself and laughed.

I said, “Terri, are you uncomfortable?”

She laughed and said, “The problem with having a cute ass in really tight jeans as a transsexual is there is no fucking room for a hard-on and you’re story gave me one raging boner. If I were a girl, I’d just be wet.”

I said “Terri, take your jeans off and make yourself comfortable.”

Terri smiled, stood up and dropped her pants. She’s wearing a thong and to my delight her ass looked like a young woman’s ass. But I had to laugh when she turned around.

I said, “Holy shit Teri, you’re well hung and you got that thing stuffed in a thong? Take that thing off and let your cock loose.”

Terri dropped the thong, she was a good 7 inches long, she said, “You think I’m well hung?”

I said, “Oh yeah. Not bad; not bad at all.”

Terri said, “Okay. Let me see yours. Come on fair is fair.”

I looked at her and said, “Why not.” I stood up and turned my back to Terri dropping my pants and underwear. I was already bare foot.

She whistled and said, “Nice ass Don.” I spun back around and Terri suddenly inhaled. She said, “Where – in – the – hell have you been hiding that master of pleasure. Man what I would love to do with that. How big is that thing?”

I said, “About 10 and a half.”

Terri said, “Damn; and you have the balls to match. I thought you were a big guy but mmm, mmm, mmm, mmm, mmm.”

I wasn’t expecting too but I started getting hard and Terri noticed.

She said, “Oh, Don. I know I’m not what you were hoping for, but damn, I would so love to play with you.”

I walked up to Terri, kissed her full on the lips, sliding my tongue in and wrapping my tongue with hers. I gently slid my hand down; wrapping my fingers around her cock. I started long strokes; reaching to tickle her balls on the downward stroke.

She let out a moan as we french kissed. Terri broke the kiss, stared into my eyes and said, “I’m your girl tonight. Anything you want me to do. Anything you want to do to me, I’m yours.” She dropped her head back, closed her eyes and said, “Oh, shit your hand feels so good.”

She lifted her head and started tonguing my neck; sliding down to my chest where she sucked my nipples. Then running her tongue down to my navel; she dropped to her knees. Slowly she dragged her tongue the entire length of my cock. Reaching the head of my cock, she turned her head and slowly engulfed the head of my cock.

She began to tease me by flicking her tongue over the pee hole and dragging her tongue roughly under the head of my hard cock. Her tonguing was intense and I was in pure ecstasy. Then she slowly slid her lips down my cock. Slowly engulfing me inch by inch, sliding down and then sliding back; until finally, she had all 10 and a half inches down her throat. She then started rhythmically sliding my entire cock in and out of her mouth. I knew I wasn’t going to last long like this.

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