My three phases of being a cuckold...Part 2. Watching your woman

Part 2. If you read my part 1 it explains how I first hand learned that my cock was just average.....Now that I had experienced big cocks first hand I was on the road to forming my role in any future relationship I would have with a women. Gary and Gene continued to use my mouth and ass at their convenience for the year or so even though they had steady girlfriends. I also started dating a super hot young girl that lived a few houses down. It was all pretty innocent and involved some heavy petting and feeling up. Gary asked if I had scored yet and apprised him of my progress or should I say lack of. He told me his new girlfriend Joanne was about my age and was still a virgin. They had engaged in oral sex and masturbation but she was afraid of his big cock. He told me his parents were going out on Friday and he planned to take Joanne’s virginity. He also said that I could hide in his closet and watch if I wanted so I would know what to do with my girlfriend when the time came.

I was really excited that I would finally get see a girl being fucked, and a virgin at that. Gary and I planned it so that I would spend the night at his house and watch from the closet. His parents let at around 7:00 pm and he said Joanne was going to sneak out of her house and show up at his house around 8:30 pm. Gary then informed me that he would last longer when fucking her if he had already cum once. He said it would be nice if I sucked on his big dick before Joanne got there. I was ready to do anything to watch him so I pulled his pants down and went to work on his huge member. He came pretty quick and shot a big load in my mouth. Sure enough around 8:30 Joanne showed up as I hid in the closet. The closet had louvered slats so I could see out clearly and since it was dark in the closet no one could see me hiding.

Gary and Joanne started making out and after a few minutes were down to just their underwear. When he pulled her panties off I got the biggest hard on of my life – there was the pinkest, wettest, pussy surrounded by black curly hair that I had ever seen. I quietly pulled my cock out and began slow stocking myself. Joanne pulled Gary’s big hard dick out of his briefs and said “I cannot believe how huge this thing is – I have seen my Dad when he got out of the shower and his looks tiny next to yours.” Gary said “Thanks now why don’t you suck on me for a bit while I try to get your sweet pussy loosened up.” Joanne went to work sucking and licking his cock. Gary had taken out the jar of Vaseline that I knew so well and began applying it to her pussy. He started working his fingers inside her pussy and it was having the effect on her he expected. She was moaning loudly and sucking even harder on his cock. After he had worked 3 fingers into he said “I think it is time we try to slide just the head of my cock into you – you would like that wouldn’t’ you?” Joanne was so hot she just moaned an “Oh yea.”

I could not believe it I was about to see her lose her virginity to my good friend. Wow. Gary spread her legs really wide and I could see the combination of pussy juice and Vaseline coated her vagina. He greased up his huge cock and began rubbing it around the entrance to her pussy. She was breathing heavy and moaning with the anticipation being taken. Slowly Gary pushed the mushroom shaped head into her tiny little hole. She held her breath and her eyes went wide. He pushed a little harder and finally the big cockhead made it was home inside her. Joanne made a loud grunting sound like you do when taking a cuckolds brownie and then her whole body stiffened. Gary was telling her to relax and he would give her a bit more – she said she couldn’t relax so Gary taking matters into his own hands rammed the rest of his thick cock into Joanne’s love tunnel. She screamed as he hymen broke and told Gary to stop and stay still for a minute. I am sure he felt bad for hurting her but he also needed to release his load of sperm so he laid there barely moving his cock in and out of her – maybe an inch or so.

Pretty soon Joanne started moving her hips in unimister with his short strokes and rotating her hips. Gary could sense that she was finally relaxing and began to pull his cock out further each stroke. I on the other hand has a death grip on my cock and was stroking it slowly as not to cum to soon. Joanne was now breathing hard and moaning. She told him to go a little faster which he did. Pretty soon she was really moaning and saying “God this feels so good, I can feel the head of you cock rubbing the inside of my pussy and the shaft is so thick….fuck me hard now...I love this!” He proceeded to give he all he had. Joanne screamed “Oh my God I am cumming...I am cumming so hard I can’t believe it …. It feels like I ma pissing but is cum I swear.” I could not only see the fluid leaking out and running onto her thighs but I could hear the sloshing of her wet pussy. This was making Gary hotter as well and he announced that he was going to fill her pussy up. He slammed her hard one last time and just held inside her as his seed flowed right into her pussy.

They lay there and held each other for ten minutes or so while I finished myself off in the closet. Joanne let out a moan of disappointment when he pulled his now soft cock out of her and a flood of sperm leaked out of her stretched wet used pussy. She said she had to get back home before her parents realized she was gone but wanted to do this again as soon as they could. Gary kissed her deeply and said “Sure, lets meet tomorrow at the park.” With that Joanne left. When Gary came back to his room I was already out of the closed and my limp dick was just hanging there. He asked “So what did you think of me fucking her? Her pussy was so tight my cock is almost raw” I told him “I could not believe how hot that was and how she could take that huge cock of his first time like that!” He said her pussy was so wet and sticky he thought she would explode. He then asked me “Do you want to taste he pussy on my cock? There is a lot of her juice mixed with my cum on me” I was still so hot I leaned over and took his limp cock, coated with dried pussy juice and cum and sucked it for all it was worth. He got hard again but was too tired to cum. He made me promise I would let him watch me fuck my girlfriend with the time came and I said “Sure!”

I became obsessed with the image of Gary and Joanne fucking and it sped up my conquest of Michelle, my neighborhood girlfriend. My parents were divorced and during the summer my Mom worked so I had the house pretty much to myself. Michelle and I had gone past the petting state and were now getting each other off with our hand and mouths. One afternoon, during on of our oral sex sessions, I convinced Michelle to let me run the head of my cock around the opening of her pussy while I stroked it. I said it would be fun to get us both off this way and I would come on the outside of her pussy. She was turned on and agreed as long as I promised not to put it in her – she was not ready for that yet. I swore I would only rub it on the outside. I took my hard cock in my hand and got between her wide spread legs and started rubbing nice and slow along the folds of her wet pussy. She was moaning how good it felt and was grabbing at my ass. Soon she started moaning and wiggling her hips just like Joanne did. She then took my hard cock in her hand and started rubbing it on herself, and then she moved it right to the wet opening and started pushing the head into her. I was so fucking hot there was nothing I could do but push my cock all the way insider her. This was my first time and I was in heaven. It felt so wet and warm and I loved it.

I started pumping in and out of her just like Gary did with Joanne. I was really getting off on this until I sensed that while Michelle was enjoying this she did not scream, moan, or squirt her juices like Joanne did. I am sorry but I am selfish and just needed to have my first orgasm inside a pussy. When it hit me I came really hard – much better than jacking off – I could not believe what I had just did, it was fantastic. Michelle held me tight while I came in her and said how good it felt as well. You know how it is with first loves – your heart is always deeply in it and now so was my cock. Michelle said it was great and that since my Mom worked she would try and sneak over more often so we could play. This was a great day – however a cloud would soon rain on my beautiful girlfriend.

I saw Gary later that day and told him what had happened with Michelle. He was excited for me but also mad that I did not let him watch like he did for me. I explained I had not planned on going all-the-way and that she unexpectedly put my cock in her pussy. He asked if she red like Joanne did and I said “No, and she did not moan or squirt like Joanne either.” Gary said “All girls are different and maybe Joanne was just a wild one.” I told him that Michelle want to come over and play some more so I would let him know when the next session was. He made me promise to do exactly that.

Michelle surprised me the next day when she showed up unannounced at my front door. It was our first meeting since “we did it” and although a bit awkward we made out and professed our love for each other. We of course ended up in my bedroom and again had great sex. Michelle was more relaxed and I got her off orally before fucking her with my cock. We kissed and said goodbye for the afternoon. Gary stopped by later and was upset that we had sex again and I did not invite him to watch. He said to call her and see if she could come by Friday at 2:00 pm for some fun and he would be there also. Michelle answered the phone when I called and said it was sweet of me to invite her over and that she was sorry for showing up today unannounced but felt a stirring between her legs that really needed taking care of.

I told her I would tend to that stirring again on Friday if she wanted and she of course said “Absolutely.”

It was set. Gary knew she was coming over Friday at 2 pm and he would hide to watch as I had with him. The logistics in my room made it more difficult to watch because I had a solid wood door. We decided to take my Mom’s full length dressing mirror and position it on the side of the bed and leave the closet door slightly open giving Gary a full view of us in the mirrors reflection.

When Friday came we got everything ready and sure enough right at 2 pm Michelle was at my door. She looked hot. She is 5’2 weights 110 with long black silky hair and a great tight little body. We kissed and talked for a few minutes and then headed to my room. With Gary securely in the closet, we lay on the bed and began the dance of lovers. It was a little strange knowing Gary was watching but in some way made it more exciting. Here was a 16 year old boy getting ready to have sex with his 15 year old girlfriend and his 18 year old friend was in the closet watching it all happen. In an matter of 10 minutes both Michelle and I had our clothes off and were making out stroking each other sex organs. She was really wet and this time wanted to get down to screwing immediately. I was hard as a rock and got into position between her legs. She was breathing hard and tilted her hips upward, grabbed my hard cock and slid it in. This was so fucking hot. She was moving her hips to the rhythm of my pumping and begging me “ push it in farther, ram it all the way in baby I love this.” I in turn was pushing it in as far as I could and doing everything I could to make it good for Michelle. Knowing Gary was watching and listening made me a little self conscious but the felling was so good I just kept pumping away on the woman who gave her all to me. I was so excited that I came really hard and just held in her. Michelle was still rotating her hip in a circular motion like she wanted more of my cock. She said “Are you done babe? My pussy feels so good and wet l need to you to do it to me again….you want to don’t you?” I of course said “Of course I do baby I just need a few minutes to recover and I will fuck you like never before.”

I was shocked when I saw the closet door open and out came a naked Gary with his huge cock in his hand saying “Hey Michelle that was so hot. Ken let me watch you guys cause I let him watch me fuck Joanne to show him how to Do-it! I don’t think you need to wait for Ken to get his cock hard when you have a big cock like mine ready to go.” Michelle stared in awe at his big dick and finally said” Ken I cannot believe you let someone watch us make love like that without telling me. You are lucky I am still really turned on or I would be furious with you.” Gary then said that after watching me with Michelle he now knows why she doesn’t scream and squirt like Joanne. Ken you really need to fuck her hard and deep. Let me show you how to fuck a woman right!” With that he walked over to my precious girlfriend and began rubbing her wet sperm soaked pussy with his fingers. He then took her hand and put it on his huge cock. Michelle could not believe how much bigger it was than mine. She started moving her hand up and down on it squeezing tighter and tighter. Gary asked her “How does that big cock feel in you little hand baby?” Michelle said “Big hard and warm” Gary asked her if she was ready to feel a real cock in her and she just moaned a “Ummmmmmmmm…..”

Gary got in position between her legs, which were really spread wide, and began rubbing his huge cockhead against her slit. Just like she did with me my darling girlfriend grabbed his cock from him and began pushing it in her tight little pussy. Gary needed no encouragement and began applying pressure to her pussy. Michelle gave a load grunt and said “Oh my god this big cock feels wonderful in me….push it in real hard” He pulled out a little and then let her have it all. Just like Joanne she moaned and screamed about how it was rubbing the inside of her tight pussy and that this is how she needed to be fucked. Gary was truly a master cocksman with a huge tool. He held her legs up and pounded her unmercifully. Michelle screamed that she was going to come and begged Gary to push it in real deep and hold it there while she shot her cream all over his big cock. Gary did as asked and she went into orgasmic spasms like I have never witnessed – even more intense than Joanne’s. Michelle just lay there with her mouth open, barley breathing, and her eyes glassy. Gary said to me”Ken that is how you make your girlfriend cum bro.” He then told Michelle it was his turn to get off and started slow humping her. She was really enjoying his deep slow thrusts and you hear the juices leaking out of her pussy being pushed in and out. Michelle told me “I love you Ken but this is most fantastic fuck I have ever had….I love his huge cock and my girlfriends were all wrong when they said size doesn’t matter…it does and I need ‘em BIG.” I just sat there with my own 6” hard cock in my hand jacking off as I watched Gary service my sweet 15 year old girlfriend. She was moaning again and said” I can’t believe I am going to cum again on his big cock…oh my god its cumming….oh oh oh” and sure enough she started to spasm on his cock as she held him tight and pushed her tongue into his open mouth. You could tell Gary loved taking my girl right in front of me and would now make her his sex toy. Gary picked up the pace and finally I saw his balls tighten like I had so many times before and he unloaded his man seed into my precious girl. Michelle held him tight and said “Shoot your cum deep inside me, it feels fucking great, your cock gets even bigger when you are cumming and I love it…..keep cumming in me please, fill me up, mix your cum with Ken’s…..I love this.”

After several minutes of deep soul kissing and hugging Gary finally pulled his semi hard cock from my baby’s pussy. It was dripping with their and my cum and made a kind of pop slush noise as it slipped out. My beautiful Michelle’s pussy was stretched wide open and was very red. It took almost a full 2 minutes before Gary’s sperm started leaking out her stretched pussy. I am sure that is because his cock was buried so deep in her when he came. Michelle just laid with her legs spread, looking more satisfied than I had ever seen her. The cum was really starting to run out of her stretched out pussy when Gary said ”You know Michelle, Ken used to suck my and Genes cock all the time and loves swallowing my cum. Do you want him to clean our cum out of your pussy?” Michelle looked at me as if to say – please say he is just kidding. I just shrugged my shoulders as I slowly stroked my hard cock. Michelle asked Gary when the last time I had sucked him off and he said two weeks ago. She looked at me and asked ”So at the same time you and I were making love you were sucking Gary’s big dick and swallowing his load?” I was really embarrassed and never thought Gary he would divulge our secret. There was no sense in lying, Michelle had just cum all over Gary’s cock and was now probably going to let him fuck her whenever he wanted so I came clean. I said “Yes I did. It is not like I am gay. I have no desire to kiss men or suck on small dicks it is just that Gary and Gene have the kind of cock I wish I had and I felt like it was my duty to service them.” She asked “Did you feel like it was your duty to get fucked by that huge pole as well?” I said “In the back of my mind when I saw that you did not react to my fucking the way Joanne reacted to Gary’s big cock that in time you would need to experience fucking a real man with a huge cock. I did not set this up for that it just happened….I am really sorry.”

Michelle looked at me and then at Gary and said “Well your duty doesn’t end with sucking Gary’s big cock so get over here and clean out my cum filled pussy. Since I now know you like the taste of his cum I will make sure you get all you can – from my pussy of course.” I started licking the cum out her while she and Gary made out. I was torn because I knew she would be fucking him and hopefully me, and that my secret was out. I really loved her and wanted her to be happy. Michelle did keep fucking me and made me invite Gary over whenever he was available. We broke up when she went off to college but Gary and I still talk about what a hot piece of ass she was. As I said earlier I now knew what a “real fucking” was and that it took a big hard cock to make a woman really scream. This pattern repeated itself with several of my super hot girlfriends. They all loved my tongue and Gary’s huge cock. I finally met an married the woman of my dreams and that story is next…….