Monica

I met Monica a couple of months ago at her workplace, a massage parlor downtown. When she is working she goes by the name of Cherry. I came in for a massage, hoping for more, and we bonded instantly. Mostly we talked, but she gave me a great massage after an amazing BJ and I was in heaven. She gave me her phone number and we went out that weekend and really vibed. I was amazed because there is quite a gap in our ages -- she is 26 and I am a young 71. The next week I went to see Cherry at the massage parlor again, something about seeing her in a skimpy dress in that environment turned me on. I liked knowing that she fucked other men but that I was special. This time we spent almost the whole hour fucking. I am on the small side and she said she liked that, said the guys with bigger dicks hurt her and tired her out. She said she liked the way I felt inside her and that not many men gave her orgasms. I was quickly catching feelings for her.

We continued to see each other in and out of the parlor -- she liked when I came to see her at work. She said it gave her a break from fucking strangers who did not know what they were doing. Sometimes we had sex, sometimes we just talked. She would tell me about her day, about the guys who came to see her, how much they paid her, and the weird shit some of them wanted. Many of the guys would not last more than 30 seconds inside her -- she said they were easy money! One guy offered her $1000 to fuck her bare and cum inside her pussy but she refused -- she is not stupid and values her health. And she is not on birth control.

Usually I see her during the day when she is not so busy -- I never want to replace a customer -- but today the time slipped away from me and I really wanted to see her so I came in the evening. Cherry (Monica) is a petite at 4'11" and 95 lbs with gorgeous B cup natural breasts. She is mixed Asian and the most beautiful woman I have ever seen, no exceptions. If a customer ever asks for a lineup at the parlor he always picks Cherry. She is so small and fragile looking I always worry that a customer will be too rough and hurt her. But Cherry says she always stays in control of the session and takes good care of herself. We spent a wonderful hour together that evening with a lot of sex and some talking. As I was leaving the parlor she reached up on her tiptoes and gave me a big hug in front of the glass exit door.

As I hugged Cherry goodby I was facing the door and saw a man coming in. He was a big man, about 35 years old, well over six and a half feet tall, and weighing more than 250 lbs. Not fat but sturdy and muscular. The kind of guy you just know has a huge dick. As he ducked slightly to clear the doorway I understood immediately that he was her next customer. She had not seen him yet as she was facing away from the door. When we stopped hugging she turned around and saw him. She winced in anticipation as she realized what her next hour would be like. I got sick to my stomach thinking about what was about to happen to Cherry and realizing there was nothing I could do about it.

Being her sweet self, Cherry took his hand in hers -- she could hold on to only part of his huge hand with her tiny fingers -- and lead him into the massage room. I took one last look as I started to leave -- her head was level with the middle of his chest and that was with her heals on. The size contrast was extreme as they walked into the room and shut the door. I just stood there, frozen, imagining what was going to happen, it was as though I could see and hear through the door.

She would get him settled, telling him to get undressed and lay on the table, and then she would leave the room for a few minutes. As I stood there I saw her leave the room -- she saw me standing there and looked at me with a scared but determined expression on her face and I realized how much I loved her. After a minute or two she walked back into the room with the usual tray that held oil, hot towels, lube, and a condom.

As she entered the room I imagined him standing there naked, facing the door. His penis was flaccid but still larger than mine when it is fully erect. She shuddered as she told him to lay on his stomach. She was wearing a cute, short dress with no underwear that showed off her tiny body, nice ass, and perfect boobs. She squirted some oil into her hand, stood at the head of the table, and started massaging his massive shoulders. As she worked her way down his back his right hand reached out and grabbed her ass -- his hand was gargantuan, he easily held her whole butt with one hand. As she bent over his head to reach farther down his back her breasts brushed his head, she could not really help that contact and it was a plus for most customers. She was not sure how he would respond but she knew he could not get any bigger than he already was. He made a guttural noise that sounded like he was enjoying himself.

She massaged as far down his back as she could reach and then walked around the table and climbed up the side, moving his legs apart a little and sitting between them. She continued the massage, working on his lower back, his glutes, and down his legs. She massaged between his legs and brushed his balls as she did for all her customers to make sure they were maximally stimulated so she would be in a good position to negotiate services when they flipped. Somehow she doubted that he needed the extra stimulation but she could not see his dick because he was laying on it and she wanted to make sure.

After about 15 minutes of massage she climbed off the table, shuddered, took a deep breath, and told him to turn over. He was a little engorged, not fully erect by any means, but she could see he had a monster dick and was scared to think of how long and thick it would be when it was fully hard. She tried to put his size out of her mind as she massaged his arms and chest and then asked him if he wanted a hand job -- she knew there was no way he would fit in her mouth or pussy. He looked at her with hungry eyes and said in a deep, bass voice, "I want to fuck you!" She shuddered again. This was the point when she would normally tell a customer that he was too big for her and have one of the other girls take over. Only she was working by herself tonight, the other girls had gone home. He looked so determined and intense when he said those words she was afraid to tell him no so she just said she would see what she could do.

As I stood outside the massage parlor front door, frozen by what I had seen, I imagined what was going on inside the room with the man and Cherry. I imagined her trying to fit his huge dick in her mouth to give him a BJ. Even with opening her mouth as wide as she could she would be able to fit only the very tip in her mouth so she would manually stimulate him to get him hard. I imagined Cherry on her back with him on top, her head buried under his chest as he forced his huge dick into her tiny pussy. As he pushed harder no one could hear her cries of pain -- he was just too damn big! I imagined him sinking his 12" dick deep in her tiny pussy, pumping away. I tried to imagine what she felt like buried, suffocating beneath his huge body, his dick repeatedly slamming her so hard that each time it hit bottom she cried out. Through the wall I could see Cherry totally covered by this huge man, barely able to breathe. I just cried as I stood there knowing there was nothing I could do to change the course of events. I felt helpless.

What was actually going on in the room was different from what I imagined. His dick was massively thick and 12" long -- far bigger than any she had seen, and she had seen a lot. He had wanted to do her bare but she had refused. Of course he brought his own XXXL rubber just in case, hers would never fit. As she rolled it down his dick, her tiny hands looked even smaller next to his enormous dick. She was petrified and fascinated at the same time. She surreptitiously measured his erect unit with her forearm -- they were almost the same length. As she applied lube, lots of lube, to his dick and her pussy, Cherry grimaced, not knowing exactly how this was going to work. He gently lifted her and put her on her back, sideways on the table with her pussy at the edge. He lifted her legs in the air. The large man stood facing her, stooping a little so his cock was at the same height as her pussy. He was surprisingly gentle for such a big man and he smelled good too, clean and fresh -- she relaxed just a little as he smiled at her.

As he started gently rubbing his penis on her clit, Cherry started to get excited and wet. After a few minutes of rubbing he started probing her pussy with his massive staff. It went in a little and then a little more, slowly deeper and deeper with each stroke. Cherry did not believe what was happening, his massive dick was inside of her -- not all the way, of course, but it felt good. She relaxed a little more. He started pumping in and out, only the first third of his dick entering her but that was as big as many of her customers' entire dicks -- it felt good and she started rubbing her clit to enhance her pleasure.

Ever so slowly he went deeper -- anyone watching would wonder how that huge dick fit into her tiny body. If you looked carefully, each time he entered her you could see the faint outline of his dick raising the skin on her tight tummy. In and out, up and down, she was getting wetter. He pulled out and asked her in his deep voice to get on her stomach for doggy. She was dripping wet by this point and willingly complied. She lay with her face on the table and her butt in the air. He stood on the table, squatting, towering over her, and entered her from behind. In this position he could easily go deeper inside her. Each time he stroked she felt his hot unit go deeper and deeper inside her tiny pussy. He reached under her and held her breasts with his hands as he increased the length of his strokes. Her nipples hardened and she felt rhythmic contractions rocking her body. He felt her vagina repeatedly clamp down hard on his penis and release, making him move more quickly -- he had never been stimulated like this before.

The man wanted to see her face when he came so he pulled out again and flipped her over, a little more roughly this time. She spread her legs and held them over her head as she waited for him to enter her again. He was not gentle about getting on top and going inside her. As he thrust inside her she could feel his bottom rib on her mouth -- his head was miles above her. He was pumping deep and fast now, his weight crushing her and the table banging on the floor. Involuntarily the rhythmic contractions began again. He was full out on top of her dwarfing her tiny body and she was riding the wave.

I was still standing outside and when I heard rhythmic banging coming from the room I could not stand it anymore. I walked past the masseuse standing in the hallway, straight toward the room Cherry and the man were in -- I had to do something, I had to save her. The masseuse saw where I was going and started yelling, "You cannot go..." but it was too late. I opened the door and burst into the room to see exactly what I had feared: The man on top of Cherry thrusting his massive dick into her tiny body.

I could barely see Cherry underneath him. "Get off of her!" I yelled and he stopped, noticing me for the first time. Cherry managed to look at me from under his chest and gave me a strange, satisfied smile. The guy just looked disgusted with me and started fucking her again, a little more slowly this time. He lifted his body until he was kneeling between her legs, pushing her hips up in the air, and kept thrusting, taking his cock all the way out between thrusts. From my position I saw just how big his cock was and I could not believe the whole thing was fitting into my Monica's tiny, sweet pussy.

She looked at me and said in a blissed out voice, "He fucks me so much better than you ever did, he makes me feel so satisfied." After a few more strokes she went on, "I always wondered what a really big dick would feel like inside me but I was too afraid to try." She made the sweetest noises as he continued to fuck her and then she had an orgasm. I could tell by the change in her breathing, the change in the sounds she made, and the enormous smile on the face of the man with his dick deep inside her. I knew the walls of her vagina were squeezing his penis tightly -- I had experienced that with Cherry only one time -- it felt amazing and made me cum before I knew what was happening.

I just stood there as they fucked, feeling the tears welling up in my eyes. Cherry looked at me and smiled sadly. I felt like a pathetic, worthless piece of shit. I knew she would never be satisfied with me again if she ever even allowed me in her sweet pussy after her experience with this man. I felt a pain in my stomach and started to cry silently. At the same time, I felt an excitement in my loins that I did not understand. I got a tingling feeling in my groin and started to get hard. I did not know what was going on, I was feeling like shit, ashamed and crying, and at the same time getting uncomfortably hard. I loved Monica/Cherry and it moved me to see her so happy and satisfied.

As I unzipped my pants Cherry smiled her sad smile at me and said, "You are so small and pathetic." I looked at my hard cock and then looked at his as it went in and out of her. I knew I was pathetic, my cock was not even half the size of his, and I was totally humiliated. Cherry called me over to them and had me stare at his cock close up as it penetrated her tiny pussy, in and out, in and out. As I started crying for real, the tears streaming down my cheeks, I realized that I was stroking myself. It felt good in a sick kind of way. I imagined how a guy with a micro penis must feel when he enters a woman and she asks if he is in yet.

Cherry told the man to stop and I figured it was all over, she had had enough, she was hurting and wanted him to stop -- I only hoped he would pay attention to her and not continue to force himself on her. He looked at her questioningly and pulled out. Now that I could see the full length and girth of his penis I was in disbelief. No wonder she wanted him to stop. When she took the condom off his penis I figured she would finish him off with a handy. I went into shock when she told him to enter her again -- bare. I never believed my little Monica would do something so reckless. He looked at her for a moment, got a shit-eating grin on his face, and flipped her on her back and sideways on the table so he could go back to fucking her in standing missionary.

Cherry told me to stand right next to him and I watched as his bare penis slowly entered her tiny, wet vagina. I was torn, terror and disbelieve on one side, and total stimulation -- this was the hottest thing I had ever seen -- on the other. He started pumping harder, faster, and deeper -- he was balls deep inside her now as she moaned and rubbed her clit. She was getting louder and louder and he was breathing hard, running out of breath. Cherry told him she wanted him on top of her and he quickly flipped her around and got on top of her. He pinned her legs next to her head, his entire weight on her tiny body. I could barely see her head and did not know how she was able to breathe. She was screaming. He was pumping for all he was worth, his guttural sounds getting louder and louder.

I continued to stroke, as though it was me giving her this amazing bounty of pleasure. They both reached a crescendo in unison as he slammed into her with the full weight of his massive body. The table was creaking and banging as it hit the wall and I knew everyone in the building could hear what was going on. As they continued I wondered what little Cherry was feeling. After a couple of minutes he slowed, lifted himself off of her with his hands, and continued, gently going in and out of her. He kept this up for a bit, winding down, and then pulled out and rolled off of her so he was laying beside her.

She kept her legs spread and told me to come around and look at her pussy. I reluctantly did as she requested and gagged as I watched his load of cum start pouring out of her vagina. Not only was he huge, but he produced massive amounts of cum. The man with his still engorged cock exposed, looked at my penis and started to laugh. Cherry started laughing with him. I hated myself, I felt so small, so incompetent, and so humiliated. They kept laughing together, as though at a private joke. By this time I was crying full out and did not know what to do so I just stood there watching as they started making out.

Eventually the man left, holding her close and kissing her passionately on the way out. After he left I just looked at her. I was totally wrung out, emotionally drained, tears dried on my cheeks. Monica -- I still wanted to think of her as my girlfriend despite the pain -- said, "You can make love with me if you want -- I do not think I will have any more customers." She was trying to be sweet but she made it sound as though I was just another customer. She was still filled with his seed -- I could see it dripping down her leg. And she looked very content. I desperately wanted her but I felt so rejected.

She walked over to me and held me close, putting my hand on her pussy so I could feel his cum still dripping out of her and I got hard. She lay on the table for me, smiling a little sadly feeling sorry for me. She moved her legs apart a little. I got on top of her and put my penis inside her dripping pussy. I had never fucked her bare but that seemed to be OK. She did not spread her legs for me but she did not resist me either, she just lay there like a limp rag doll. I imagined how she treated a new customer she did not particularly like and just had to put up with.

I slid into her effortlessly and felt as though I was going to throw up as I felt his hot cum surround my penis. Cherry held me tightly but still just lay there as though she had no interest in what was going on. My whole body began to shake -- I was hurting so badly deep, deep inside, I just wanted to die. I felt sick as I started going through the motions, knowing she was not wet for me but filled with his cum. I tasted vomit in the back of my throat as I mechanically moved in and out. When I finally came she pulled away as though she did not want me inside her any longer than necessary.

I dressed and left, crying softly, walking into the dark night with drizzle and fog outside, not sure if I would ever see Monica again.