A Real Small Problem

c7o

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As I started to drive home I was thinking, I rode to the clinic in a van, now I am driving home in my own new car. When I came to the clinic, I was no more than a boy in a man’s body. Now no one can say that I am not a man.
All the way home my nerves were on edge, what will my Mom think of me now. My life long friend, Debbie might not like me any longer. Debbie & I had been only friends, nothing more. I would like for us to be more than just friends, but the new me might not be what she wants.
I only had 4 days before I needed to go to college. I do not know what Debbie has set up for me for a dorm room. I had not been home for 3 months, a lot had happened in the last three months, my life was going to be completely different.
I did not see anyone when I pulled into the drive. As soon as I parked, I hurried into the house to find Mom. I called for Mom as soon as I got into the house, when she came out of the bath room, she stopped & just looked at me. Finally she said, Tom you have changed so much, are you OK?
I told Mom that I felt great & I hoped that I looked OK. Mom said that I looked great, it just that I had changed so much.
Mom told me she needed to call Debbie, as she had promised to call her as soon as I had arrived. I was really nervous. I told Mom that I would use the bath room, while she called Debbie. In a few minutes, I could hear two people talking, so Debbie must be here. My stomach was a ball of nerves, when I walked down the hallway.
I could hear Mom telling Debbie that I had changed, that I had grew into a man over the summer. I heard Mom tell Debbie that Tom will explain it all to her, just be ready for a big change.
It was now or never, so I walked into the living room, where they were. Debbie jumped up to hug me, she just stopped, looked me up & down my body, then I saw her smile at me. The silence was killing me, so I asked Debbie, do you like what you see.
Then Debbie said that she was just shocked seeing how I had changed. I walked forward towards her as I asked, do I get a hug. Debbie looked so sexy in her shorts & a tee shirt, my dick was trying to get hard. It felt so good when Debbie put her arms around me, kissed me & told me she had missed me. My dick seemed to have a mind of it’s own, was pushing against Debbie. Debbie whispered in my ear, that something else had grown over the summer, it must like what it sees.
I whispered to Debbie that I loved the way she looked, but something seems different about you, you look so sexy.
Mom broke the silence when she said, Tom you need to show Debbie your new car & I think you need to tell Debbie all about your summer. You both have a lot to talk about, take Debbie for a ride.
Debbie stepped back as she said, she had a lot to tell me also, we only had 4 days to plan for college.
Then Debbie said that she needed to tell her mother where she was going, give her 15 minutes, come over to her house, so her Mom could see the new Tom. I had not thought about Debbie’s mother, she was almost like my second mother to me. Our mothers had both taken care of each other’s kid, when a baby sitter was needed. Debbie’s mother had been divorced for a long time, so both of our mothers had been without a man in the house for a while. Our mothers treated each other almost like they were sisters.
I guess Debbie & I, had felt almost like brother & sister to each other. I was not sure that I could still think of Debbie as my sister, I wanted something more.
Mom said before I go next door, she wanted to tell me that Debbie’s mother knew where I had been all summer. Mom said that she had to talk to someone, about not seeing that I had not been developing correctly. & she hoped that I did not mind that.
I gave Mom a big hug, told her not to worry, she was great mother & that I loved her. Mom said, before I went next door, take things slow with Debbie, I saw how you hugged each other & the look in each others eyes.
 

c7o

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Next door, I just walked in the back door like had 100’s of time before, but it felt different this time, maybe I should have knocked first. Both Debbie & her Mom were sitting at the table talking. Debbie told her Mom, see I told you, Tom is a real hunk of a guy now. Debbie’s mother got up from the table, gave me a long hug, as she whispered, Tom take it slow, you & Debbie are meant for each other, just do not hurt each other. She gave me a kiss as she told us to go talk, tell each other everything, & that she loved us both.
As we got out to the car, I told Debbie lets put the top down, it is a nice day. I asked her where she would like to go? Debbie said lets get a coke & fries at the local café, then drive out to the state park, we can sit & talk there. We stopped, got the coke & fries, headed out to the park, it was only 10 minute drive. We found a quiet spot in the park, under a shade tree, parked so we could talk.
Debbie wanted me to tell her where I had been all summer. I told her it was kind of a private matter, it was hard to discuss with her. .
Debbie told me that I was her best friend, that I could tell her anything, she would understand. So I figured I had better start at the beginning, with my small problem. I asked her she ever wondered why I never had a beard or other features of my body, that the other guys had.
Debbie did not seem to understand where I was trying to go with this. So I just started by telling her, that I had never started puberty, so nothing developed that should, including down below.
I told her that Mom’s boy friend, Don got me an appointment with a doctor who had a clinic for this sort of a problem. I had been at the clinic all summer taking experimental hormone treatments. You can see over the summer I developed as much in 3 months as most guys take years to do.
Debbie asked, did you develop down below also? I told her that I had gained a lot, maybe too much. She said what do you mean, maybe too much.
I told Debbie that the doctors were worried, that maybe the hormone treatments were too large, because I gained more than the other patients. The drug company that was running the tests, gave me this car, a full scholarship & money every month. I guess they were worried that I might sue them or something.
I guess Debbie was wondering how I had changed, as she was looking down at my lower body, so I changed the conversation. I asked her what she had to tell me.
Debbie said she would start with what she did this summer. I have not seen my Father for over 10 years, since my parent’s divorce. I got a letter from my father’s lawyer, Mom & I had to go out to New York City to see the lawyer. My Father had been killed in a car accident, in his will he left everything he had to me. The estate was quite large, so I am set up pretty good for my life.
Since I had the money, I decided to give myself something that I have wanted since puberty. I have always thought my boobs were small, so I gave myself a boob job. Tom, I thought you would notice & say something.
I said, when you hugged me I thought you felt different, but I did not want to say anything. But I will say now, that you are very pretty & dressed in short shorts & a tight tee shirt, you are one sexy lady.
Debbie now said that we need to talk about college, where are going to live, classes, & activities. Debbie said that she could not get a dorm room for either one of us, but that she had found a real nice large apartment close to school. It has 4 bedrooms, she found two other girls for two of the bedrooms & Tom the other bedroom is yours.
I asked Debbie, how can it work with 3 gals & 1 guy in the same apartment? Debbie said she had talked to the other girls, explained the deal to them. Both said we were all adults & would make it work.
Debbie said she wanted to try out for the cheerleader squad, the other two girls are also trying out & Tom, I signed you up for the tryouts too. Debbie said there would be 8 girls & 4 guys on the squad, it should be a lot of fun.
 

c7o

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I told Debbie that I would love to do what you want, but there is no way that I can wear the tight pants that the guys need to wear on the cheer leader squad. Debbie did not seem to understand why, I could not wear them. I guess I need to explain to you, Debbie the bulge in the pants would cause problems & be embarrassing.
Debbie looked at me & said, it can not be that big to cause problems. Tom let me see.
Debbie, I think that is a bad idea, but I will, if that is what you want. I looked around to see if we had company, I did not see anyone, so I started to loosen my belt. I dropped my pants, then my under shorts, then I turned towards Debbie.
Debbie looked, without saying anything for a little bit, then she said, Tom you are huge, but I want you on the cheerleader squad with us, we will have to think of something.
I put my pants back on & asked Debbie if she thought we could ever be more than just best friends.
She looked at me, then slowly her eyes dropped, before she said anything. Tom we have been best friends all of our life & I hope will be best friends, always. Let’s give ourself, one year, dating other people to be sure, because I never want anything to stop us from being friends. Please give me one year, I will give you one year, then ask me again. If I say yes I want it to be forever, please be patient for both of us.
Then she smiled & said, Tom, can we be just friends with benefits, for now, I want to see if that big thing will even fit in me, but let’s wait until we go to school, so we can have a bed & lots of time.
Now let’s go home get our mothers, go out to eat for supper
 
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c7o

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Debbie had given me a list of things, that she thought that I would need for my room, as I had not seen the room. So I had went shopping at the mall, bought the items needed. I saw a shop selling high dollar sport clothes, so I went in, started looking around. I did not see a clerk, was about to leave, when this nice looking older lady walked out of the rear of the store.
She asked if she could help me, I told her it was kind of personal, did she have a male clerk. She told me that she owned the store, was the only full time person during the day. She then said, that she had probably heard most things already. So please tell me your problem & we will try to solve it.
I started by telling her that I was starting college next week & I was going to try out for the cheerleader squad. The pants are tight, I am afraid that I would have an embarrassing bulge showing.
The lady smiled, looked down at my pants, while saying that she might be able to help me. She led me to a counter towards the rear of the store, with all kinds of supporters on it. She looked at me, then looked thru the supporters until she found one that she thought might work.
I asked how it would hide me, she said it was soft elastic material & would not chafe me. She handed it to me, told me to try it on, there was dressing room in the rear. When I had it on, she would see how it worked. When I got in the dressing room, I stripped, looked at the supporter. It had a pouch to hold my balls tight, then there was insert along the right leg to put my dick thru to hold along my leg, to help hide. I had trouble getting my dick thru the insert, when I did, the head of my dick stuck out the bottom. I started laughing looking at myself in the mirror.
The lady heard me & asked if there was a problem. I told her, yes there is a small problem. She said let me see, as she opened the door. I turned around, then she saw the head of my dick sticking out along my leg. She looked at it, finally said that looks like a big problem.
She said the company makes supporter to size, but they are not cheap. She said each one would cost about $125.00, we would need to measure, for the size.
I told her the cost was OK, but how was we going to measure. She looked at me as she said, that she would lock the store, get a tape measure & that she would do it. As she left I took the supporter off, now naked, I was not sure this would work. The lady was middle aged, but looked great & was going to measure my dick.
When she came back, she looked at my naked body & said oh my, I have not seen a naked guy in a long time, you look so great. She kneeled down in front of me to measure, I could see down the front of her blouse, as she started to measure. I told her, that she better hurry to measure my limp dick, having a pretty lady handle my dick, it was not going to stay limp very long. She hurried measured the length & around my dick. As she looked at my dick, she said that I was bigger soft, that most guys were hard. You are almost 9” by 6”, how much bigger do you get?
I guess looking at my dick close, was too much temptation for her, she started kissing the head of my dick. As I started to grow, I could hear her, start to breath faster. She then got up & said lets go in my office, I have a big couch in there, I want that dick in me. As we walked to her office she was taking her blouse off, then the bra dropped behind her. When we got in her office she pulled her pants & briefs down in one motion. When she turned around, she had nice boobs, sagged a little, but her nipples were large. The only other lady I had ever seen naked was Betty, she shaved her pussy, this pretty lady was hairy, quite different. I told her that I did not even know her name, she told me it was Linda, as she laid down on the cough & spread her legs apart. She said that she had put up a sign, saying gone to lunch, so she did not have a lot of time.
Linda said she had a big dildo that she used regularly, so she hoped she could take all of me. Linda was in a hurry & she said, she wanted it now. When I put my dick against her pussy, she was really wet, I could feel hot pussy lips, when she shoved towards me. Linda was really horny, she wanted me bad, so I was not about to hold back. As I started to push in, Linda started bucking her hips, most of my dick was in, but a couple inches or so left. I could feel a restriction on the head my dick.
Linda was having trouble breathing as she asked, are you all in? I told her no, 2 or 3” more. She said you are bigger than my dildo.
Linda said fuck me hard, but before you cum, I want to feel your big balls banging against my pussy, now stud get with it, I do not have too long. When a lady says she wants it hard & fast, a guy has to give it to her, so I did. As I was fucking her I was moving from side to side, trying to make more room. I could feel something giving away, as my balls started bouncing off her pussy. Linda was really getting loud, she hollered is that all you got stud. So I pushed her legs over my shoulder & gave her all I had, when I did Linda seemed to lose it. She was bucking & tightening her pussy around my dick, I could not hold back, I shot my biggest load ever.
When I started to pull out, cum started oozing out around my dick onto the sofa, Linda reached down with her fingers got some, put to her mouth to taste. She said you taste good.
I started to find my clothes, as Linda wiped her pussy of cum. Linda asked how many supporters, did I want. I told her 6, she said that she would just order a dozen, have them overnighted to her house. Linda told me she had a good friend, who would love my dick. If you will come by my house tomorrow evening, have supper with them & spend the night with us two ladies, the supporters are on me.
I got her address, promised to be there at 6:30, I was really starting to enjoy this new me.






 

c7o

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That was quite a shopping trip to the mall, got what I needed, met a very hot horny older lady. Maybe, was going to get what I needed to allow me to try out for the cheerleaders like Debbie wants.
en I got home, there was a message on the home phone from a doctor near the college, wanting me to call for an appointment as soon as I arrived at college. Another message from Debbie, wanting me to call her.
Before I could call her, she had heard me come home, she just came over to see me. I was sitting at my computer, when she walked in, short shorts, tee shirt, no bra, with her nipples showing thru her shirt. Debbie sits on my lap, gives me a big kiss with a lot of tongue. When she pulls away, Debbie can feel my dick getting hard, reaches down starts playing with it thru my pants.
I ask Debbie, what has gotten into her, she says nothing yet, but I hope that changes. Debbie told me that she had always looked at me as her best friend, nothing more. Ever since you came home, things have changed, then I saw that big dick of yours, I can not stop thinking about it, wondering if it will fit in me. I have been so horny, my pussy is so wet, I do not want to wait until Sunday night to have sex, then Debbie asked, where is your mother.
I told Debbie, that our mothers had went to a party at my mother’s boyfriend’s house. Don had asked one of his friends over to meet your mother.
When I told Debbie that, she stood up, pulled her tee shirt over her head, showing me her great boobs, with nipples hard, standing straight out. Then she pulled her shorts down, she had no panties on, so her very inviting bare pussy was starring me in the face. Debbie asked if I liked what I saw?
As I stood up, I put my arms around Debbie, kissed her, then told her that I had been dreaming of seeing her naked most of my life. Debbie asked, why did I not tell her how I felt. I told Debbie that she had always been beautiful & I looked like a kid, I was afraid that I would make her mad & she would not hang out with me. She was really the only good friend that I had, while in school.
Debbie took my hand, let’s go to your bed room, I want to fuck that big cock. When we got to my bedroom, Debbie pulled my tee shirt off, yanked my shorts & my undies down in one shot. Then Debbie told me to lay back on the bed, she wanted on top, she knew that b[g cock was going to hurt, so she wanted to be in control.
My cock could not have been any harder, it was standing straight up, oozing precum like a big fountain. I tried to kiss her, she told me to just lay back & enjoy, that she just wanted see if she could fuck that big cock.
Debbie stood over me, bent her knees until her pussy touched the head of my cock. I could feel the heat from her pussy, I wanted to raise my hips to feel more of that great pussy, but I just laid there waiting. Debbie took both hands, pulled her pussy lips apart, while moving her hips around. I could feel the head of my cock trying to get in as Debbie pushed down. I could feel her pussy starting to stretch. Debbie moaned as the head of my cock went in a couple of inches. Debbie stopped as she said, your dick is so big, it feels like I am sitting on a log.
It was really hard for me to hold still, with my dream girl sitting on my cock. Debbie started moving her hips, adding weight on my dick, if I had not been so hard my dick would have bent in the middle. Debbie’s pussy was so tight, then she started to tremble, her pussy was trying to squeeze even tighter on my dick. I could not help myself, I started to fuck her, as she was putting weight on me. A few strokes & Debbie started yelling just fuck me. Debbie was too tight to use very long strokes, but I was moving my dick from side to side as I stroked, trying to enlarge her pussy, to make it easier to get deeper.
I started fucking harder with each stroke, getting a little deeper with each stroke. Debbie started a strong orgasm, when she did I grabbed her hips, pulled her butt down on me as I pushed up. When my dick went all the way in, I started cumming, I pulled Debbie tight against me to keep my dick as deep as possible, as I moved my dick around in her pussy, this was driving Debbie crazy.
Debbie went almost limp on top of me, her boobs resting on my chest. Debbie whispered to me that was the best sex that she had ever had, Tom, you are going ruin having sex with any other guy.
 

c7o

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Debbie asked, do we have time to do it again before our mothers come home? I told her, that we had time, how would you like it? Let’s try doggie style & see if I can take that big dick, but go easy I am going to be so sore tomorrow.
With all my cum leaking out of Debbie’s pussy, we sure did not need any more lube. Debbie laid over the end of the bed, it was just the right height for me standing up, behind her. I put the tip of my dick against her pussy, put my hands on her hips, pulled her back as I pushed in. I went about half way in, started to slowing fuck her pussy, trying to go a little deeper each time. Debbie was still so tight, so I started moving from side to side, up & down as I went in & out. Slowly I could feel, that I was making more room for my dick. When I had about two inches left, I could feel the end of my dick hitting something, stopping me.
Debbie said, she thought I was hitting her cervix, no one had ever done that before, go easy. Slowly I pulled Debbie back against me, as I held still. I could feel her opening up as I pulled her back. Then I was all the way in, she was so tight, that it almost hurt.
Debbie looked back at me & said, Tom keep it all the way in & fuck me, I feel so full. I started fucking her, using short strokes, keeping the head of my dick past her cervix. Debbie’s whole body started to tremble, her pussy squeezing my dick. Debbie started screaming, Tom fuck me harder I have never felt like this before. Still using short strokes, I started pulling Debbie, back hard against me, every time. Debbie was in continuous orgasm, a few more strokes of my dick, I could feel my cum starting to pump out. I pulled Debbie back, pushed against her hard, trying to get deeper. Debbie was screaming, I can feel you squirting into me. I just held Debbie against me, until I started going limp.
I pulled out, sat on bed next to Debbie, before she got up she reached over to kiss my dick & then said, Tom, your dick makes me feel so good. When she got up, I held her, in my arms. I told Debbie that I had ordered some special supporters, & was to go to her house the next evening to pick them up, so I could not see her then.
Debbie said that was OK, as she was going to one of the new roommates house, was to meet the other roommate there. Then Debbie told me that I needed to keep Sat. night free, the other roommates wanted to meet us for supper, to get to know you. We then heard my Mom’s car pull into the drive, Debbie got up quick, said she would go out the back door. She ran out naked, holding her shorts & tee shirt, trying to put them on as she ran. She hollered back that she would call in a few minutes.
 

c7o

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In a few minutes Debbie called, she was laughing & excited, when I answered. I wondered what was
going on, Debbie said as she was running between the houses on the alley, the neighbor behind our house was carrying out the garbage. The neighbor told me as I was running, my boobs bouncing, that he would bring the garbage out every night if I would run naked.
Then Debbie said, we have been good friends for a long time, after tonight it was going to be hard to stay, just friends. Then Debbie said she would call me Sat. afternoon & tell me what time she would be over so we could go meet our roommates.
Then Debbie said she was going to bed, Tom when I get up in the morning, I will be thinking of your big dick, because I know I will be sore, walking bowlegged, good night.
After Debbie hung up, I was thinking, after tonight, things between us would never be the same as before. I hope it will be for the better.
When I woke up Friday morning, mom was cooking breakfast. This was the next to last day before I left for college, so I was going to spend most of the day with Mom. As we ate breakfast, Mom asked, what I was doing at lunch time. I told her I planned to spend the day with her, but I had evening plans.
Then Mom said, that she wants me to have lunch with Don & her. Mom said, Don had asked her to marry him last night & she had said yes, Don has something he would like you to do, for him.
Don was taking us to a nice restaurant, so I needed to wear a suit, I hoped the suit the drug company bought, fits. We still had 1-1/2 hours before we needed to go, so I took a shower, was sitting on the bed, I decided to call Debbie. When Debbie answered, I asked how she felt this morning?
Debbie said, she was sore, but she was really happy we got the first time out of the way. Now we both knew, we could make each other happy.
I told Debbie, Mom was getting married. She already knew, her Mom had told her, I forgot she was there last night. So Debbie how did your Mom like her date? She said that he was really nice & they had another date Sat. night.
I told Debbie that I needed to get dressed, to go lunch with Don & Mom. I told Debbie to have fun with our future roommates, tell them hello, for me. I am looking forward to seeing them.
[t1] As I was looking in the mirror, I was naked, it looks like my dick as grown a little more, maybe just the way it is hanging. I will find out next week when I have to see this new doctor. The clinic found the doctor for me, a doctor that teaches part time at the college, also has her own practice. I never had a woman doctor before, not sure how I will handle that. The Doctor’s nurse left a message that I should come to the Doctor’s office at 4:30, Monday afternoon.
But now I had better hurry up, get dressed for our lunch date. Mom hollered up the stairs, are you ready, we do not want to late. When I came down the stairs, Mom was waiting, I had not seen her dressed up for a long time. I told her that she looked great, really sexy for a guy’s Mom.
The drive to the restaurant only took 10 minutes, we were a couple minutes late, when we walked in the door. Before the waiter could get to us, to seat us, Don walked up to get us. Don led us to a booth towards the rear, a beautiful young woman was already seated there. When Don introduced the young woman as his daughter, Becky. I looked at Mom, you should have told me Don had a beautiful daughter. Mom sat opposite Becky, Don next to Mom that left me next to Becky. As I sat down, Becky gave me her hand to greet me, then leaned over, kissed me on the cheek, welcomed me to her family.
I guess we were going to be brother & sister by marriage.
We all ordered, as we waited, Mom explained that she had asked Becky to be her Maid of honor. Then started to talk. He said, that Mom & he had talked, they wanted to make their wedding a family thing. Then he asked me if I would be his best man. The only answer that I could give, was big yes, after all it was my Mom’s wedding.
When we finished lunch, Don asked if I could take Becky home. Don said that they were going to look at houses this afternoon. They wanted to sell both of their houses, buy a house together, that they could call their own, less memories that way.
So I led Becky out to my Mustang, when I helped her in, I could not help but notice that Becky had great legs, as her dress pulled up. When she raised her butt to pull it down, I got a great view. As I walked around the rear of the car, I tried to rearrange my dick, so it did not show. As I was getting in, Becky looked at me, looks like you liked the view, you got. A very awkward moment, I tried to change the subject. I told Becky I needed to be somewhere at 7:00PM, but the rest of the afternoon was her’s, if she wanted.
Becky asked if we could just ride around, talk, get to know each other better. Becky said she was in premed at the state college, which was a two hour drive from here, but only 30 minutes from where I was going to go to college. She wanted to be a doctor like her Dad. I told her I was hoping to get into computer programming.
Becky said, that her Dad had told her a little about your difficult child hood, that he had helped to get you in to a clinic that might help me. She looked at me, asked did it help? I told Becky that is very hard to talk to her about this.
Becky looked at me and said, Tom, we are not going to be real brother & sister, but I have to start sharing my Dad & you, your Mom. So I would like for us to be able to talk to each other, like family that neither of us have ever had.
So I started to tell her of my childhood, of being teased, of never having a date. I told her about my best friend Debbie. Then Mom met her father, he had offered to try to help me. This last summer, my entire life had changed, when I went to the clinic.
Debbie wanted to know what the clinic was like & what medicine that I had been given?
I told Becky, it was sort of a sex clinic for guys, I was given experimental medicine in shots, then as a gel. All of the guys there had not developed fully, but I was the only guy there, who had not started puberty. For me when the medicine was given to me, I started puberty in overdrive. I told Becky, that I had a doctor’s appointment with a lady doctor, who also teaches part time. When I told Becky the doctor’s name, she said that doctor teaches one of my premed classes.
Becky looked at me as she said, you know sometimes experimental drugs have side effects. Tom I hope you will call me after your doctor appointment, I would like to know how you are doing.
Please give me your phone, I will put my cell number in your phone. I gave her my phone as I told her that it was getting late, I needed to take her home. When we pulled into her drive, I started to get out, to get her door, Becky reached over stopped me from getting out, she gave me a kiss on the lips, as she got out, Tom please call me, I hope we can be good friends.
As I drove to a house, where I needed to please two older ladies, my mind was wandering all over the place. The last few days had been very different, very exciting, but mentally tiring.








[t1]