Shemale Stories

[a9127]

The following story was inspired by a drawing of a beautiful young femboy from a post made by man74tiop2 in the “Lovely Shemale Toons” thread.

“Hi.” I heard someone say while standing in the line for lunch at the Spring LGBT conference for teens and young adults that I help organize every year. Instinctively I turned around. “I really enjoyed your presentation this morning Dr. Andy. I liked what you said about being true to who we are. And standing up to bullies. That really meant a lot to me. I wish I had known someone like you when I was younger. I hope you don’t mind me saying that. It’s nice to meet you. My name’s Bobby.” “Nice to meet you too Bobby. Glad you enjoyed it.”

We chat a little and It turns out you will graduate this May with a degree in Sociology from one of the other Indianapolis universities. “Would you like to join me for lunch?” “Sure!” We find a place out of the way to sit because I sense that you want to talk to me privately. “You know Dr. Andy I’ve always identified as gay but I’ve always felt like a girl kind of—do you know what I mean? In your talk you said your first girlfriend was transgender.”

“Well Bobby that’s really up to you. However you identify it’s all good. Have you ever talked to anyone about it before?”

“Well I tried talking to my Mom and Dad but they just said I’d ‘grow out of it’ and my dad said he didn’t want to raise a ‘sissy.’ The counselors at my school weren’t any help either. My mom sometimes treated me like a girl but I think that was just to protect me from my dad. I never really liked ‘guy’ stuff. Like I was never any good at sports and didn’t like getting into fights or stuff like that. I heard you were like some kind of football star in high-school and college. One of your students said you could have gone pro. I hope you don’t mind me asking… How did you identify when you were younger?”

“As I said in my talk earlier, I always considered myself ‘straight’ but there was this one friend of mine I was really close to. His name was Stephen and we used to hang out all the time. He was an amazing dancer. He had told me that he wanted to perform on Broadway someday. Which he since has. A long time ago he transitioned and she has been known as Stephanie ever since. She’s the person I mentioned in my speech."

“You know I’m really a good dancer too! And I love music and art. I would have liked to have played sports like baseball or soccer but I never felt big or strong enough. Also a lot of the other boys called me names and said they didn’t want a ‘faggot’ on their team. And football scares me. I’m not like you—I’d get killed!”

“Anyway Bobby, everyone thought we were gay. Even my Mom and Dad. I was fortunate that I had a very understanding and accepting family. So did Stephanie. That makes a big difference. People talked shit about us behind our backs and I got into more than a few fights. In high-school, Stephanie and I attended a private school where everyone was a lot more accepting. We dated for a long time.”

“Wow. That’s awesome Dr. Andy. You said it was like 1992 or something when you guys met? I wasn’t even born yet!”

“I’m not THAT old!” I say laughing. “We were only like 11 or 12 when we met but sometimes I think things are worse today Bobby. I am truly sad that there are so many ignorant people in the world.”

“So, do you think I am gay or trans?”

“Bobby, you are the only person who can truthfully answer that question, but just having met you I think you are a very intelligent and thoughtful young person. If you want to identify as gay that’s fine. If you identify as trans that’s OK too. Or if you decide you are straight that’s also OK. The important thing is that you be true to yourself. No one else’s opinion but yours matters. No one can put a ‘label’ on you. Ever.”

“I’ve never really thought about it like that before Dr. Andy. Thanks.”

We both smile at each other and for the first time I notice how just how beautiful you are. Maybe 5’7” with shoulder length blonde hair and light blue eyes. You have a very pretty face. You are wearing a rainbow t-shirt and super tight jeans. You are very fit but not big or muscular. And you seem like a genuinely sweet person.

“You know I really do feel like a girl most of the time but I’ve always considered myself gay because that’s what everyone says about me.”

“Well it’s perfectly OK to be gay but only you can decide that. It doesn’t matter what others say.”

“Did you ever think you were gay Dr. Andy?”

“At first, yes. Stephen and I were very close. Our families thought we might be gay. I decided it didn’t matter…”

“What did Stephen look like? Did you ever kiss him Andy? And did you know I’m almost 22?” you say excitedly. Then “Sorry, I meant ‘Dr. Andy.’”

“You know Bobby it’s almost time to go to the next activity. This is a group exercise where each one of us shares our experiences. Good and bad. No one gets to say anything negative. You don’t have to participate and it’s totally confidential. I’ll be walking around to each group to observe.”

“I wish you were in my group” you say wistfully.

“Well maybe we can talk some more later, Bobby. It was nice to meet you.”

For the time being we go our separate ways. There are no rules against “dating” or developing friendships among participants unless a participant is a student at your own school, or a patient of yours, or under 18. You are none of the above. Still, I can’t help but wonder what an almost 15 year age difference would be like.

Later that evening, we run into each other again. “Hi Andy, (I noticed you left off the ‘Dr.’ part) I learned a lot about myself in those workshops. Would you like to hear about it?”

“Sure.”

“Maybe we could go for a walk?”

“OK. But we will have to be back before it gets dark.”

Giggling you say “well I don’t want to keep you up past your bedtime…”

Copyright © 2017 AMS

[a9127]

Continued from "Part 1" above...

It’s a beautiful evening. I notice that as we walk you gradually move closer to me. You tell me that you think you are more gay than trans because you still feel like a guy sometimes. But you realized that you enjoy many things that might traditionally be associated with girls and women. Also you took a ‘personality test’ that indicated that you are more ‘female’ than ‘male.’ You say that “maybe I’m just a femboy?”

You tell me that you have had only two "boyfriends" in your entire life and you add that you have always felt like the more submissive one in a relationship. Then you tell me about your career plans to be a social worker and counselor for LGBT students and how you would like to go back to school to get your Master’s.

Finally, you ask me about some of the other women I’ve dated and if I was ever married. You don’t think I seem gay at all and think it’s "awesome" that I had a male friend that I fell in love with even though I was very young at the time. You tell me more about yourself and ask me more about Stephen/Stephanie. Things like how we handled "haters" and "bullies" and how and when we really knew we were more than friends. The more we talk the more I realize we do have a lot in common.

Time flies and it has grown dark. I ask if you would like to go somewhere for dinner. You say “I’d love to” and we find a nice restaurant in Circle Center. We spend a lot of time just getting to know each other and by the end of the evening you have totally dropped the “Dr.” part and we are now just calling each other “Andy” and “Bobby.”

During dinner I realize I feel something for you that I’ve not felt in a long time. I wonder if you feel the same. We are both over 18 but I’m still not sure about dating someone almost 15 years younger. You don’t seem to be giving our age difference a second thought however and say “I’ve had a wonderful evening with you Andy. I’m glad we met.”

Heading out to the parking garage, you notice a black Hellcat sitting by itself. “Andy, is that yours? I love cars! It’s awesome!”

Opening the door for you, you stop, turn around, and standing on your tiptoes kiss me. “Thank you for an awesome evening Andy. I’d love to go for a ride in this…”

We leave the parking garage and get on I-465. “Geeze Andy the speed limit is 55 MPH. What do they think this is 1981? Let’s find another road.” We head out on Interstate 74 and I find a place where I know it’s safe to make a speed run. Pushing it up to just over 150 MPH (well under the Hellcat’s top speed) you say “Omigod! We’re gonna die…” and start laughing. After I slow down, you say “You know I was just kidding. I feel totally safe with you. That was really exciting. I loved it! By the way, where do you live Andy?”

I pause for a moment. Part of me thinks I probably should take you home. “In Zionsville. Where do you live Bobby?”

“I’m staying with friends on the Southside. I’m originally from Tennessee. When I graduate next month I’m getting my own apartment. You can come and visit me anytime…” you say smiling at me. “So are you gonna take me back to your place or do you want to stay with my friends? I really like you and just want to be with you Andy.”

We head up to Zionsville and turn onto my street. It’s late and the Hellcat wakes up a couple of the neighbors—a few lights come on. You find this funny and then as we pull up in front of my home you say “Jesus! What kind of place is this? My friend’s house would fit in your garage.”

After I help you out of the car, you put your arms around my neck and we kiss for a very long time. When we separate, you look up at me and say “Andy, I’m 21. Not 14… You of all people should understand what I’ve been through my entire life. I’ve had to do more growing up than most people twice my age.”

We kiss again and I pull you close to me. I can feel your cock through your jeans as you rub up against me. You are a great kisser and it’s a while before we come up for air.

“Let’s go inside Bobby.”

“Well duh…” you say giggling. “I thought maybe you wanted to do it on the front lawn. We could put on a real show for your neighbors!”

Going up the staircase you say “how many bedrooms does this place have anyway?”

“Six.”

“So which one is yours?”

“Through those double doors.”

Standing by the bed you pull your t-shirt over your head as I unzip your jeans. You slip them off and I remove your panties. We make out for a while. Just taking our time. We run our hands all over each other’s bodies and I kiss and massage your nipples. Your cock is only about 5”. I suck and tease you ever so slowly as you lay back on the bed. You moan as I finger you gently while I continue to suck your beautiful cock.

Your body is absolutely gorgeous. Toned and athletic. When you are ready, you pull your long sexy legs up so I can enter you more easily. Fucking you is every bit as wonderful as I had imagined. You don’t take very long to come and I shoot my load inside you seconds later.

Relaxed, we just lay there. You look at me and smile. “Andy that felt so good. I’ve never had sex like that before. It’s always been from behind and so quick it’s over with in seconds. Sometimes I don’t even come. You are the first guy that ever really made love to me.”

Holding you next to me we fall asleep. Waking up the next morning, I notice that you are already out of bed. Your clothes are still on the floor. Heading downstairs I smell something good cooking. You have on one of my bathrobes and are making breakfast for us. “My Mom taught me. Hope you like it sweetie!”

I put my arms around you from behind and kiss you as you lean your head back. “Stay here with me Bobby.”

“I’m not planning on going anywhere Andy. By the way what’s that heavy bolted metal door in your den for?”

“Oh it’s just a ‘tornado shelter’ you know how bad Indiana weather can be…”

“Yeah I bet it is Andy…” giving me a “knowing” look and smile. “You will have to show me around down there sometime…” you say giggling.

Copyright © 2017 AMS

[a9127]

Returning home from giving exams, I look around the house for Bobby only to find she’s out back sunning herself. Today was about 85 F and perfect. Walking across campus all I could think about today was her.

“Hi gorgeous…” I say. “How was your day?”

“It was really good Andy, I got accepted into a Master’s program in Sociology at UIndy and also found a couple jobs working with LGBT youth this summer. Maybe when you have time you can go with me to check them out. Everyone seemed to know you.

“Well you know Bobby I think it’s wonderful that you want to do something like that. I’m really proud of you sweetie. You know I’ll help you out financially and of course you can stay with me. I’m sure you can get a scholarship too. That's something I can help you apply for. You’ve certainly got the grades for it.”

“You know Andy I was thinking a lot about how I identify myself. Remember how I told you at first I thought I was gay, then maybe a ‘femboy’, then I started thinking about how I’ve always felt more like a ‘girl.’”

“I love you no matter how you identify Bobby.”

“I know that Andy. The first time we ever made love I really felt like a woman. And the way we snuggled up like we were a couple afterward. I loved just being close to you. It was SO much more than the sex which was great. You know I don’t have a lot of experience. While you were gone today I was thinking that I feel more like your ‘girlfriend’ than anything else."

“It’s something that only you can decide Bobby. I told you when we first met it’s all good.”

“Yeah but I’ve always had a feminine side. I guess being with you brings it out more.”

“Don’t worry about rushing to judgment. Everything will fall into place in time, baby.”

“I was actually thinking of changing my name to ‘Bobbi’.” Would you like that?

“Yeah. Its whatever YOU want to do. But yes I think it’s cute.”

I notice that you are wearing a hot pink bikini and since we’ve been together you’ve been letting your blonde hair grow longer. I also detect a hint of mascara and cheek blusher. You look totally hot. Your lightly tanned body with just a thin coat of lotion looks SO sexy.

“Andy, would you rub some lotion on my back?”

“Sure, baby.”

“While you lay face down on the lounger I gently rub the lotion onto your shoulders. Gradually I work my way down to your ass and legs. You moan and say “OOOOOhhhh that feels so good.”

You turn over onto your side as I lean over and kiss you. You say, “I love you Andy.”

“I love you too Bobbi.”

Through your tiny pink bikini panties, I can see your erection straining for release. And your nipples are very hard. You have perfect small natural breasts. God you are so beautiful. As we kiss again I put my hand on your thigh and gradually run it up your leg until I’m massaging your cock through your panties. Your skin is so smooth. Pulling your panties down, your cock is free to grow to its full length and slowly I begin to suck you very gently and teasingly.

“Don’t’ stop baby” you say breathlessly. “I wasn’t planning on it sweetie” I say giggling slightly.

“We better get on the blanket Andy. I don’t think this lounge will hold both of us” you laugh.

Sliding down onto the blanket you stretch out so I can access every part of you. Stroking your cock ever so slowly I kiss and lick your amazing body all over. I can’t believe how fit you are. Your breasts, your thighs, your tummy, and of course your cock get the most attention. Occasionally we pause for a very long kiss. “God Andy, I’m not sure I can stand this much longer. Next time you might have to tie me up in your ‘tornado shelter’ you giggle.

“Oh. So that’s what you think is down there…” I say trying not to laugh. I knew you were too smart to fall for that “tornado shelter” explanation.

“Andy, I’m not very experienced but can I try something?”

“Sure, baby.”

Taking my cock in your mouth you begin to suck me off. For someone who says she doesn’t think she knows what she’s doing you seem like an expert.

Soon I’m the one that’s begging to cum!

Turing over on your back you look me in the eyes and say “Fuck me baby…”

Entering you gently, I go very slowly at first. You seem to know exactly what to do and soon I explode inside of you while your cute little cock spurts onto your tummy. Afterwards I lick it all off.

“I love you Bobbi.”

“I love you too Andy.”

“Are you still worried about our ‘age difference’ Andy?”

“No.”

“That’s good baby.”

“Let’s go get cleaned up then have dinner then later we can look over the letter of acceptance to grad school you received. I’m so proud of you Bobbi!”

Copyright © 2017 AMS

[a9127]

Along one wall of my den behind my desk is a heavy steel door. I tell most of my friends that it’s a “tornado shelter” and leave it at that. Here in the United States especially the area called “tornado alley” it’s not uncommon for people to have such a safe haven. Indiana is just East of this area but gets quite a few tornadoes, some of which are F4’s and even F5’s. Today, in fact, as I’m writing this, we had a tornado warning just south of Zionsville and about 10 minutes ago, hail.

“Andy, you said you’d show me what’s behind the door. I’d love to see it” Bobbi says excitedly.

“You sure you want to sweetie?”

“Yeah. You know I’ve already figured it out, baby.”

“OK. But it’s totally up to you. If you don’t like it that’s alright. You know I love you. So whatever, it’s OK.”

Opening the door I turn on the lights, they are dim. You follow me downstairs cautiously. You have total trust in me but I can tell you are a little apprehensive, and clearly excited. You are wearing very short cutoff jeans and a grey t-shirt cropped off just below your breasts. And you are barefoot.

“Geeze Andy, I’ve never seen anything like this before except in videos. Is this where you bring your dates?” you say giggling.

“Well not everyone likes this kind of thing. I’m not into pain or torture but I enjoy tying my partners up and keeping them on edge, sometimes for hours. You know Bobbi if you want to go back upstairs we can.”

“No Andy. I’m kind of turned on by it. Even when I was very young, I’ve always fantasized about being held captive by a powerful lover who would do whatever he wanted to me—but not someone who would ever hurt me. Do you know what I mean?”

“Yeah, I do Bobbi.” I say as you run your hand along the edge of a heavy oak table with wrist and ankle restraints. I can see the outline of your now very hard cock under your shorts.

“You know, Andy, I was with someone when I was still a teenager who tied me up and was really rough with me. At first, I thought it would be awesome but he wouldn’t stop and then started to hurt me. I got really scared and have never tried this with anyone ever since.”

“Well that person was a real creep Bobbi. He’s lucky I didn’t get ahold of him. He should probably be in jail.”

Laughing you say “Ohmigod! He’d fucking shit his pants if he saw you. You’re more than twice his size.”

“If you ever do decide you want to try any of this stuff we can--if not I understand. I love YOU Bobbi. I’ve totally enjoyed our last few weeks together. I meant what I said when I asked you to stay here with me. Our relationship is SO much more than this.”

“I love you too Andy. What do you think about this chair? I’d let you strap me in if you wanted. I trust you totally baby” you say as you stand up on your tiptoes and kiss me.

“Why don’t we do this, Bobbi? Have a seat and get used to how it feels--I won’t do anything unless you tell me too. OK?”

You sit in the bondage chair and place your arms and legs as if you are strapped in. “Wow I didn’t know my legs would be so far apart!” you giggle. “It actually IS kind of a turn on Andy. Kiss me baby.”

I lean over and kiss you very deeply. You kiss me back and our tongues are all over the inside of each other’s mouths. Reaching down I run my hands up your thighs, lightly stroking your cock through your shorts. I can feel it react to my touch as you let out a moan. Then I run both my hands up under your t-shirt and play with your nipples massaging them gently. Then we kiss again. You look up at me and smile.

“Andy, that feels wonderful. You can strap me in anytime…”

Gently, very gently, I fasten all of the straps. Along the way I pause and ask you if everything’s all right.

“God yes!” you say excitedly.

Soon you are tightly strapped in and I unzip your jeans as your very hard cock springs out. I can see there is a lot of precum. I kiss you on the mouth as I run my hand along the shaft ever so lightly stroking the head of your cock with my fingers. You say “Oh fucking god… that feels SO good, Andy.”

“Well I’m just getting started baby.”

“Shit, I guess I’m really in for it aren’t I?” you say laughing.

“Yeah you are, but you do know you have the power to say ‘stop’ at any time Bobbi.”

“Why would I ever want to Andy?”

Kneeling before you I slowly start to suck you off. I bring you teasingly close to cumming then back off ever so slightly. After a while I can tell you are really frustrated as the tension builds. LOL

You have been desperately trying to come but to no avail. Pausing for a second I look up at you. You are drenched in sweat and all your muscles are straining against the straps. Our eyes meet. It’s time. God you are beautiful Bobbi.

Returning to your cock I continue to suck you using a slow and steady motion. Gradually I can feel your orgasm building until you literally explode into my mouth. I swallow all your cum. Your back arches as you pull against your bonds. I have been masturbating while sucking you and my own orgasm is very powerful but brief. Still on my knees I collapse between your legs onto your lap. You lay back against the chair and sigh. Your breathing is very relaxed.

“I’ve never felt anything like that before Andy. Wow. Do you have anything where you could fuck me while I was like maybe tied to a torture rack or something?”

“Yeah sure Bobbi, that would be awesome.”

“Andy, I’m not scared with you. That was amazing. I think I’d let you kill me if you wanted.”

Laughing I say “Well I wouldn’t go THAT far but I’m really glad you liked it baby.”

After undoing the straps. We hold each other for the longest time. I kiss you on top of your head and stroke your long blonde hair. “God I feel so close to you, Andy. I guess I really am your girlfriend aren’t I?” you say as you hug me very tightly.

We take a shower together downstairs and put on two of the extra bathrobes I keep for guests. We lay on the couch and watch TV for a while. We are both very tired and soon we have fallen asleep, you on top of me.

Copyright © 2017 AMS

[a9127]

It had been a long day for both of us. I had to visit several clients as well as work very late on my grading and you, having just finished your final exams, started working as a counselor at the youth center. Worn out, we go to bed, kiss and say goodnight.

Rolling over onto my side and half asleep I hear “Andy? What do you think about our relationship?”

Never sure exactly how to answer this question correctly—usually whatever answer I give is always the “wrong” one… LOL. So I just say “I love you Bobbi you mean everything to me.”

“I love you too Andy but what do you think about us?”

“What do you mean Bobbi?”

“Well… do you remember when we first met, I asked you if you thought I was gay or trans.”

“Yeah. But that’s for you to decide. No one else can label you. I love you the same Bobbi no matter how you identify.”

“I know that Andy. But how do YOU see me? Do you think I’m a gay guy? Or maybe a femboy?”

Fully awake now I realize we aren’t going to be going to sleep, at least for a while. Besides I know how important this issue is to you so I say “Bobbi you asked me how I felt about you. You can identify as whatever gender you choose, dress however you want, hang out with whatever friends you want. But I see you as a beautiful, extremely intelligent, caring, loving, young woman.”

“You don’t think I’m gay?”

“No.”

“Would it matter to you?”

“No.”

“What if I told you I really was gay?”

“Then I guess we’d both be gay. Because I’m in love with you Bobbi. I think you’re totally hot. So that would make us gay lovers.”

“I love you so much Andy” you say while snuggling close and then kissing me.

“Can I ask you something else Andy?”

“Sure.”

“Would you meet my family?”

“Yeah. Like when?”

“Like next weekend? My Mom and Dad said they wanted to have us over for dinner. I’ve told them a lot about you. My Dad is a big college football fan. He said he saw you play in the Rose Bowl in the early 2000’s. He told me you were awesome. I’m too young to remember it. Sorry!”

“Gee thanks for reminding me how old I am…” I say laughing.

“Andy?”

“Yeah Bobbi?”

“Well since we’re up you know what I was thinking?”

“Probably the same thing I was.”

You look up at me. Then you slide the straps of your nightgown over your shoulders baring your beautiful breasts. Saying nothing, you just lie back, look at me, and smile. We kiss and make out for a long time then using a little lube I gently massage your prostate. When you are ready, I enter you and we fuck each other slowly and gently. We take our time just enjoying each other. I think your little cock is so cute when it spurts onto your tummy. Our orgasms are relaxing and afterward we just lie there snugging and kissing.

Next Sunday afternoon we head over to your parents for dinner. I am a little nervous about meeting them. You told me I had nothing to worry about but still it’s just one of those things.

We take the Hellcat. I just hope your Dad doesn’t work for Ford. LOL Your Mom meets us at the door. Bobbi introduces me and her Mom is very friendly. “I’ve heard so much about you, Andy!” she says.

Her Dad is in the living room watching football. “He extends his hand and says “Nice to meet you Andy. Maybe you can tell me what is wrong with these Colts!” “A lot” I say laughing. “Where do you want to begin?”

Her Mom says “Bobbi was telling us how you two met. Ohmigod! The way she talks about you!”

I noticed that her Mom called her “she.” I take that as a good sign.

Her Dad ads “Bobbi used to be a ’tomboy’ We never knew whether he wanted to be a guy or a girl.” Umm… unfortunately this is NOT a good a sign. I don’t like hearing anyone referring to Bobbi (or any transwoman) using a male pronoun. “He could fight though. Once I saw him deck this bully that called him a ‘faggot.’ I still don’t understand much about this transgender stuff. That Olympic guy on TV—Bruce or ‘Caitlyn’ or whatever became a girl so I guess maybe that what’s happening to Bobbi. You know a lot more about this stuff than we do.”

Her Dad continues, “Whatever Bobbi is we still love him. We are glad he met someone. There used to be all kinds of weirdos hanging around.”

“Daddy! Those were my friends from the LGBT group at school! They were NOT ‘weirdos’!”

“Well Andy looks like a nice young man to us. And he’s successful in business and obviously very smart. Look at the car he drives. I dunno, he must think of you as a ‘girl’ Bobbi because he sure as hell doesn’t seem gay to me.”

I don’t say anything. Even though I’m offended I’m trying my best not to laugh. Bobbi looks at me and rolls her eyes as if to say “See what I had to put up with?”

There will be lots of time for me to talk to her Mom and Dad after we get to know each other better. I’m crazy in love with their daughter and I don’t want to mess this up with an argument right now. When the time is right, we’ll have a talk. I guarantee it.

In the kitchen, her Mom says to me “So you and Bobbi really like each other? I always did think Bobbi was different somehow. If she didn’t have a well… you know… I’d swear she was a ‘real girl.’ Even when she was little.” I cringe when Bobbi’s Mom uses the phrase “real girl.” “She’s a really sweet person I’m sure you know by now. As her Dad says we don’t really understand exactly what ‘transgender’ is. All we know is what we’ve seen on TV. But I think that’s what is going on with Bobbi. And I know she cares about you very much. So tell me, are you ready for all of this Andy?”

Bobbi comes into the kitchen, kisses me, then holds onto my arm tightly. Her back stiffens and she looks her Mom right in the eyes. “Mommy, you and Daddy have known I was this way for years. I know you have always loved and supported me even though you didn’t understand fully what was going on. Many people in our society still don’t. What if I had been born a genetic girl? You’d love me as your daughter. Well--think about it. I AM a girl! And I’ve met someone I’ve fallen in love with. This weekend I wanted you to meet Andy and get to know him. He’s very special to me. I love you Mommy and I want you and Daddy in my life also. But you are going to have to accept that this is who I am.”

Dinner is ready and we go into the dining room. With a lot of the awkward stuff out of the way, our conversation goes much better. We talk about many things and her Mom and Dad actually seem very nice. I don’t think Bobbi’s parents are bad, like many people, they just don’t understand. It turns out Bobbi wasn’t kidding; her Dad is a big sports fan and follows college football. He has seen me play several times on TV and once even took Bobbi as a little kid to see us play. He even remembered the interception I returned for a touchdown that day. He had always hoped Bobbi would grow enough to play football in high school. I bet he never realized his future son in law was the starting middle linebacker in that game. Strange how stuff works out.

After getting to know me better, and after realizing just how much in love we are, Bobbi’s parents seem to be more accepting of her as a female. And us as a couple. I think like many things this will just take time. Overall, I had a nice evening and think I won her parents over. But we will still have our “talk” one of these days. I can’t let some of the things that were said go unchallenged. Just think of it as “educational.”

After dinner Bobbi and I go for a walk in the woods behind the house. “I hope you didn’t mind my Dad. He just doesn’t ‘get it’ Andy. My Mom sort of does but it would be easier for her if I had just been born a genetic female. She really wanted a daughter. I know how it appeared but they really do love me. And they didn’t know at first exactly what to make of you. You really gave them something to think about. A six-foot-four former college football hero, successful teacher and businessman, who has been married twice to ciswomen, falling in love with their ‘son the sissy’ and acting like there’s nothing unusual about it. How fucking crazy that must have been to them!” Then you start laughing so hard.

“I’m glad I met you Andy. I really mean that. Did you know I used to play in these woods as a little kid? I always was ‘Sheena’ or ‘Wonder Woman’ or ‘Supergirl’ or ‘Lara.’ I could climb that big tree over there. See?” There is a full moon. The moonlight makes your beautiful eyes look almost surreal. You put your arms around my neck and say “I love you Andy.”

Copyright © 2017 AMS

[a9127]

Went overseas on business recently. Have read so much about other’s experiences with escorts decided to try it myself. While I was there, I met this incredibly beautiful girl in a bar and took her back to my hotel room for a night of wild, unprotected, amazing sex.

The next morning, when I woke up, she was gone. A few days later my cock became inflamed and started to itch. By the next day it had turned black and looked infected.

The first doctor I went to said “Very, very, bad. Cock will need to be cut off!”

Thought to myself, “No way! I need to get a second opinion.”

Went to see another doctor. He said “That is absolutely the worst case I’ve ever seen. We must cut your cock off right now!”

Again, I didn’t like that diagnosis either, so I went to see a third doctor.

After a thorough examination, the third doctor said “Not a problem. Take two asprin. Wait a day. Cock will fall off all by itself."

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Continued from the story “Meeting Her Parents”…

“I love you too Bobbi.”

The night is warm and the beautiful moonlight makes everything seem magical. Your parents’ live way out in the country so there’s not anyone else around for miles. And they long ago went to bed. So it’s like the two of us are the only people on earth.

We kiss and make out for the longest time. I can feel your hard little cock as your body presses up against mine. I get down on my knees and unzip your jeans. I use my tongue to lick up and down your shaft, occasionally taking all of you in my mouth. I slide your jeans off, then your panties and top. You hold my head tightly as I suck you ever so slowly. Then I reach around and gently work my finger into you so I can massage your prostate as I continue sucking and teasing you. “Jesus God Andy, I’ve never felt anything like that before. Oh Fuck!”

Stopping for a moment I work my way up and down both of your thighs. You have long muscular legs and your skin is so silky. You kneel down and run your hands all over me. “God you’re so strong, Andy.” I kiss your tummy and your breasts, licking and gently biting your hard nipples. I think you have an amazing body. Just perfect, Bobbi.

We go at each other like this for quite a while. You work your way down and suck my cock. You run your tongue around the head. It feels great. Stopping, you look up at me and say breathlessly “I want you to take me from behind Andy.”

We stand up together and walk over to a nearby tree. You lean your head back and I kiss you on the neck. Then our mouths meet. While we kiss I feel your ass with one hand while jerking you off slowly with the other. You just moan and say “Oh God Andy…”

Gradually I work my fingers inside you while continuing to slowly stroke your cock. You instinctively bend over using your arms to support yourself against the tree and spread your legs. I kiss your beautiful ass as I keep stroking your cock which is now dripping precum.

Standing up I use both hands to steady myself as I enter you from behind. You gasp slightly. It’s hardly the first time I’ve been inside you but I think you were surprised at how good it actually felt. I remember the time you told me how much it hurt with a former partner and how rough they were. The last thing I’d ever do is hurt you Bobbi. I want this to be an amazing experience for you baby.

You continue to lean up against the tree for support as I fuck you. You are still very tight and I feel like I am going to cum. I start stroking your cock faster and faster and I can feel the two of us getting close. Between the beautiful warm evening, and the increasing love we feel for each other there is something extra special about tonight.

We cum at the same time. There is the indescribable feeling of release then waves of pleasure. You steady yourself against the tree until I’m through ejaculating then after I pull out we both sit there together leaning against the tree. You reach over and hold my hand. We are both covered in dirt and sweat and cum. I’m not sure if I’ve ever felt like this with anybody--ever. You look over at me and just smile.

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