Lessons Learned

Story Info
She needed a favor from her gay friend.
4.2k words
4.39
79.7k
14
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
curious2c
curious2c
2,499 Followers

Melissa's story:

The dream came again. Actually it was that nightmare all over. I relived that night that date had gone bad. I had gone out with that monster on a blind date. I hardly knew the girl that set us up on the date, just acquaintances. He looked sharp and quite handsome. His eyes were piercing, and his manner was that of one used to controlling.

The date started out innocently enough. He took me to dinner, ordering for me as well as himself. I didn't mention to him that I disliked all that red meat. I wanted to get to know him a little bit before I made any judgments.

After dinner we had gone to that bar. We danced a bit, and I let him touch me in some fairly intimate places. He was bold, yet soft and gentle. I trusted him to behave. His touches grew more familiar as the night went on. We kissed at one point. His tongue was insistent, as his attitude had become.

Even then, I was not worried. I figured he was trying to see how far he could go on this first date. I never realized how far he would push things until it was too late. Offering to walk me to my door I let him into my secure apartment complex. He followed me to my door, and as I unlocked it he stepped in close.

He wants a kiss, my first thought. He came up to me and leaned in. His lips were hard on mine, crushing them. His tongue was sharp and pushed into my mouth. His hands were on my breasts. I tried to stop him. He was strong and fast. I found myself in my room, on the couch. My dress was falling off of my body, as he got rougher with me.

I still was trying to understand what was happening to me. He was my date. He had been so nice and masculine earlier. How could he be doing this to me? Had I given off a signal to him that I wanted him to be rough and take me?

While I tried to make sense of what was happening, he had gotten all of my clothes off. Naked under his body I felt his hands probing me. My nipples were hard, even though I was not interested in having sex with him. His other hand was down low, fingers in me and soon...far too soon I was wet down there.

I felt him undressing. His hot hard cock was soon thrust into me as he rutted. He cared nothing for my comfort. His intent was on him alone. His mouth was on my nipples. Teeth nipping at them as his thrusting became more and more forceful.

I felt his hot cum pouring into my poor abused pussy. I had no protection, and he was bare also. Not only could I get pregnant, he might have an STD. I was frightened as to what would happen next. His actions so far had proven to me that I had made a mistake in thinking I was safe with him.

Afterward...after taking my anal virginity. After his forcing me to lick and suck his cock until he came in my mouth. After gagging and choking me with his cock ramming down my throat. He left. I lay there for hours before finally getting the strength to get up.

I felt so dirty and unclean. I went and showered. Later I called into work claiming I was ill. I was ill...in ways I wanted to forget. Sex had always been a beautiful thing for me and then this had happened. I never had been in this situation before. It always happened to other women.

I never reported the rape. He had not threatened me in anyway except that look he had given me as he left my apartment. That look told me in no certain terms, if I reported him he would be back.

Months went by. I gradually got over my fears. I saw a shrink and she was able to help me over some of the harder feelings I had. Soon I was almost back to normal...what ever that was. I had a neighbor two doors down that had been helpful to me. I had cried on his shoulder quite a few times.

John was a gay man who had been my neighbor for years. He was always there to lend a shoulder, give a hand, and just be a friend to me. At different times I had thoughts of him and I in bed together. Always it came back to his being gay. That stopped me from trying anything with him.

He had never told me outright he was gay. I had seen a man staying with him for the first two years I had known him. They seemed to be very close and a couple of times, after they had been out partying I had watched them struggle to the door of their apartment, arms around each other.

He was handsome and nice. Shy, yet very knowledgeable about women. I thought his interest in women was weird considering his choice of lifestyle. We became friends and often were out together as buddies. I used to tell him all my secrets like he was a girlfriend. I loved him as a friend for sure and regretted not being able to take our relationship to the next level.

One day, as we talked I realized that I had not had sex for over a year. I was frustrated and horny. I was also afraid of going out with a man. I still had those nightmares of that night. Still, I had needs. Masturbating was not cutting it and I wanted to get fucked. By a man. I just didn't know if I would be able to find a man whom I could or would trust enough to have sex with.

I decided that John might have a friend who he knew could be trusted to fill my needs. I lightly mentioned it to him in our conversation. I was not expecting his reaction at all. His look, at first, was shocked. Then I saw something indefinable in his eyes. He hesitated for a bit, starting to say something several times then stopping.

Finally he agreed to try to find someone for me. His words were there but his attitude was like he didn't want to do this at all. I knew something was bothering him so I sought to reassure him that I needed to know if I was over that terrible night.

"John, you don't have to do this for me. I just want to find out if I can go on. If I am over that...night."

"Melissa, I will do it for you. I-I-...are you sure about this? I mean...don't you know someone already that you trust to do this for you?"

"You are the only one I trust John. You and I can't...so I thought you might know someone you would trust to...well...be gentle and understanding."

"We can't? Why not us? I mean, well, we have known each other for several years. You have been my best friend and I yours. Why not us?"

"Oh sweetie, I know you would do this for me but I can't ask you to change just to help me out. I want a man to fuck me. To have sex with me and do things that a man can do for a woman. I also want him to be understanding of my past and be very patient with me too. You would be my first choice if you were not...if you could...I just can't impose on you in that way John."

John's side:

I had known Melissa for quite some time. She was a vibrant and friendly lady. Her beauty was from within and she was a very sexually appealing person. Her friendship with me had been reserved, more like I was a girlfriend than a 'man' friend. Until today I had never realized she thought I was gay. It had never come up in conversation between us.

I am not sure where she got the idea I was gay. Perhaps when my cousin Ted had been living with me. We had been close as brothers for years. Ted was what one could call a 'flaming' gay man. I had let him stay with me when his dad had kicked I him out of the house.

Ted stayed with me until he met a guy and they were now together. Ted was happy and I was happy for him. His father had been harsh with him over his choice to be gay, as if it were a choice for Ted to begin with.

After Mel's rape I had been there for her. When I found out what had happened to her and what the jerk had done to her I was furious. I had wanted to ask her out so many times. I just could never find the right words.

I had found that jerk one night and he admitted to having taken her. After I got done with him I left him in a pile on the street. I hoped I hadn't killed him, but if he died I didn't really care all that much. He had hurt someone I loved very deeply.

I was there for Melissa as she went to her therapist and worked through all the feelings she had about that whole rape. She had confessed to me that she hadn't reported it and by the time she had thought about it enough to do that she realized that it was too late.

I had held her as she cried. I had been there to listen to her talk about other men and past loves of hers. I had been her confidant and 'girlfriend' throughout all this time. Now she had asked me to find her an understanding and gentle man to have sex with her.

Cruel world I live in. I love this woman and she thinks I am gay, that I don't like women in that way. Here I stand, loving everything about her and wanting her like no other, and I can't touch her like I want to.

I agreed to try to find someone for her, knowing that the search will break my heart. How could one offer the one he loved to another? How could I not have the backbone to tell her how I feel?

I know why. Because just being near her has always been enough. I figured that someday she would see me for who and what I was and we would be in love together.

I had dreams of us living as man and wife. Dreams that were about to be destroyed because she thought I was gay. I loved her more than as a friend and was afraid of losing her forever by telling her that.

I lived day to day for the next week. I never really tried to find anyone for Melissa. I was troubled by my fears and her request of me. I wanted to tell her. I wanted to be that man for her, forever.

About the middle of the second week Melissa asked me if I had any luck in finding her a solution to her problem. Knowing that I was losing my love if I did but feeling I had no other choice I told her I would by the following weekend for sure.

I talked to a few friends and after seeing a picture of her they were interested very much in going out with her. I held them at bay by not directly asking them. More like showing a picture of a girlfriend around. They were jealous of me, if they had only known what our relationship really was like.

On Friday I finally made my decision. It was the hardest choice I had ever made up until now. I had to do it for her I told myself. Over and over I told myself I had no choice in the matter now. I was truly going to be the friend she needed.

"Hi John. Had any luck in finding me a man?"

She was in good spirits today and being a bit smart-assed. I knew she was expecting me to come through for her. I only hoped my choice would be the right one for her. It was breaking my heart and I was a bit choked up in telling her about her date for Saturday night.

"Yeah. I found a guy for you. He will be gentle and understanding. I talked to him several times about you. He knows quite a bit about you. I hope that you don't mind if I told him about...things."

"Mind? Well John, I trust you. I know you would not hurt me or allow anyone else to hurt me either. What does he look like? Tall like you? Come on, give me something to work with here."

"Well, he is tall like me. His weight is around 180, no fat. He works out regularly and he is pretty healthy. He isn't gay, so you can rest easy about that too."

"When does he want to go out with me then?"

"He said he would pick you up around seven tomorrow night. Are you sure about this Melissa? I mean, this is how your last date started and all. I think you can trust him, but even I can't guarantee what will happen."

"Oh John, I know you wouldn't set me up with a jerk. I trust you and your judgment."

The next morning I got a call from the man I had picked out.

"Can't make that date tonight John. Looks like you are going to have to take her out man. Lucky dog you. I have to fly to L.A. this afternoon for a session. Sorry. Have fun."

I was upset. He was leaving me no choice but to face Melissa with my cowardice. What would I do now?

I debated just calling her, but she would have come right over after my telling her about her date canceling out on her. Then she would feel bad because she would think he was dumping her for her not for the real reason. I was in a quandary for hours. Then I suddenly realized that it was almost time for her date to start.

I showered and dressed up fairly nice. I walked over to her door on shaky legs. My greatest fear was about to come to a head. What would she say? What would she do? I almost turned and went back to my apartment. Something made me stay where I was.


I rang her bell. Waiting nervously for her to answer I almost ran. Still something kept me there. A little voice in my ear saying 'be a man stupid'.

Melissa opened her door. Her look of surprise was complete. I could see her looking over my shoulder for a man. The man who was taking her out for dinner and a fuck. When she didn't see him she looked at me confusion in her eyes.

"He was a no show?"

"Ummm...no."

"No? Then where is...you? You are taking me out? But...I thought...John, you are gay! You can't...I can't expect...Oh damn!"

"Melissa, please listen. I need to tell you something. I...uh...that is to say, you...well..."

"No, it's all right John. You don't have to do this. I shouldn't have asked you to do this for me. It was very unfair of me to ask you to find me a date. I'm sorry. So sorry."

Tears in her eyes she closed her door to me. I was stunned and very afraid. Afraid for her and her pain I had caused her by my bumbling. I walked a long slow walk back to my apartment. Then, getting to my door I got mad with myself. Angry and upset I turned and stomped back to her door.

Pounding on it I waited. Soon she answered, face wet with tears. She looked surprised at me. I calmed myself down.

"Melissa I need to tell you something. You may not like it at all. I am angry with myself for not telling you this a long time ago."

"John, please don't be angry with me. I never meant to hurt you. I know that being gay is still not a..."

"Melissa, first of all lets get this gay thing straightened out. I am not, nor ever have been gay. I am straight. My cousin stayed with me...He was gay. His father had kicked him out of his house so he came to live with me."

"But, I thought you were gay. Why didn't you tell me this then? Why have you let me think you were gay all this time?"

Stepping into her apartment I closed the door behind me. I could see a shadow of fear in her eyes. I went to her sofa and sat down. She followed and sat on the chair across from me.

"Melissa, I have not told you because I was unaware you thought I was gay. I was afraid that if I asked you out you would refuse me...it would change things between us and I wouldn't get to visit and be with you as often."

"You let me think you were just a friend to be near me? Are you kidding? You aren't gay? I told you...you know things about...Oh God!"

"Melissa, please don't be angry with me. I have lo...loved you for quite a while now. I have been torn up trying to find the courage to tell you. Then...well...your rape and the following days of pain you were suffering...I couldn't bring myself to tell you. You needed me as a friend. I was there for you because I loved you."

"You love me? You love me even after the things I told you about the other men? The rape? I asked you to find me someone to fuck me...and you tried. You did try didn't you?"

"Yes, I tried. He cancelled out, had to fly to L.A. He forced me into telling you about my secret. I am sorry Melissa. I never meant to hurt you in any way. I have really messed up things now."

I got up and left. She was crying as I closed the door and went home. I sat in my dark living room for most of the night. I felt so low, so damned lost. I had chased away the love of my life and she hadn't known my feelings until last night. I had really blown it for good now.

Melissa's story:

As John left I began to think over the last years. His revelation to me about his love for me had stunned and shocked me. I was still trying to imagine him as not being gay. He was a very handsome man and I had wanted him before this. I had a lot to think about.

His expression of love for me had been very unexpected too. I had my best friend in life express his love for me and all I had done is cry. He must have left thinking I was a first class bitch. What a mess I had made of things.

I was up most of the night as I thought about John's confession and us. I decided that in the morning I would put him to the test. If he were gay and just trying to be a friend in order to help me out I had to know.

I dressed to be a sexually available woman. I put on my shortest one-piece dress and only thigh-high stockings. Heels made up the finish to my intent. This morning would be telling. I would find out the truth about John and I.

As I walked to his door I realized I had not thought of the rape at all this night. I had just been thinking about a man I wanted and who apparently wanted me but had been afraid to tell me. I decided that I would have to be the huntress. I would have to come on strong and stay strong.

John's story:

As dawn crowned over the city and the light drifted into my eyes I remembered last night and the disastrous results. I made myself some coffee and toast wondering about how things would be now. I had left her crying. I had hurt her deeply. I had messed up.

There was a knock at my door a bit later. Stepping out of the shower I slipped a towel around me and went to answer it. I expected a buddy of mine who usually showed up about that time to talk his latest conquest from the night before.

"Mike this isn't a...Melissa? Oh...excuse me...I thought it was a friend of mine."

"We need to talk. I didn't get any sleep last night and you look like you didn't either."

"Umm...come in...I'll get dressed. There is coffee in the kitchen. You know where the cups are."

Dressing as fast as I could I wondered what she was thinking. She seemed so serious. I was afraid of what she was going to say. I was pulling on my jeans when she just walked into the bedroom.

"Whew! Nice ass!"

"What?"

"You heard me...nice ass!"

"Umm...I'll be out in a minute Mel..."

"No, you'll be here for a while. You have a promise to live up to buster!"

"Uh...I don't understand. We were going to talk. I..."

"Talk is the last thing on my mind. You have been holding out on me for several years. I want some of what you got. I have wanted you forever. I am going to have you now, no more waiting or wishing."

I was stunned. Melissa had changed into a tigress ready to pounce on her prey...me. I was still struggling with buttoning my jeans when she shoved me onto my bed. Her hands quickly made short work of removing my jeans. My underwear followed. Her eyes were on my hardening member. I saw her lick her lips as she looked into my eyes.

"I have waited a long time for this. You have a long day ahead of you so just relax for now. I want to be in charge for the time being."

"Uh...whatever you want Melissa. You are in charge."

"Good! Now that we understand each other...get that shirt off. Pronto!"

As I pulled off my shirt I saw her stripping. She was wearing a short one-piece dress that flew off and landed in the corner. Underneath she was only wearing heels and stockings. Her well-trimmed pussy was glistening in the morning light as she crawled onto my bed up between my legs.

Her hands were on my hardness and soon her lips followed. Her technique was incredible and she soon had me ready to explode. She backed off just before I lost it letting me down to earth before starting again.

I reached out and caressed her hair as she took all of me into her mouth. She moved around a bit and soon was straddled over my head. I could see her lips were wet with desire as she lowered her pussy down to my waiting tongue.

So many feelings were cascading around me. I was lost in my explorations of her when she had her first orgasm. Her knees crushed around my head and I almost couldn't breath at all. As she let loose I could hear her moaning and my cock began to throb.

Her talented oral ministrations were achieving their intent. I soon began to cum. Her pussy was still in my face so I began to lovingly and lightly lick and taste her juices as she swallowed mine.

curious2c
curious2c
2,499 Followers
12