Friend Ass Me for a Big Favor

I had known Judy for five years or so. We were good friends despite her being ten years older than me. I knew she had an eighteen year old son (Pete) who I hadn't met and a husband (Jim) who I had met three or four times. I was thirty-one at the time of this story and had just split up from my long-term boyfriend. I thought Judy's invite for the two of us to have lunch together might be to comfort me in my time of need.

We had a lovely lunch in a classy restaurant that I had never been to. She listened to my moans about my ex with great patience and made a few suggestions about how and where I could meet a new man. I could tell that she wanted to say or ask me something before she said she had a favor to ask me.

"You probably don't know that Pete is off to college next week and I wondered if I could ask a huge favor of you."

I said I would be delighted to help and asked what she wanted. She said that she felt that Pete should ask me, as the favor was more for him than me. I was slightly surprised but said "no problem". I asked when I could meet him, as I couldn't do it that afternoon. We arranged for me to go round to her house on the Saturday evening. It all seemed a bit formal but I looked forward to a nice meal and evening with Judy, Jim and Pete. So that we could all enjoy some wine (Jim loves quality wines) they offered me a bed for the night.

When I arrived it was Pete who opened the door to me. I was stunned that he was a strongly built young man standing every bit of 6 foot 3. He gave me a lovely smile and welcomed me in taking my coat. Jim was in good form and we had a great meal. There were wines to go with all three courses and they were all lovely. As we sat drinking coffee and more wine after the meal the phone rang. It was Jim's father who said that a pipe had burst and was asking Jim to go over and help. Judy quickly said she would go with Jim particularly as he had had too much to drink to drive. They said they would stay over as it was over an hours drive away.

I offered to leave but Judy said she was sure Pete would look after me and anyway he had not had the chance to ask me the favor he wanted from me. Pete seemed very comfortable with this and poured me another glass of wine.

I asked Pete whether he would be leaving a girlfriend behind when he went 200 miles away to college. With regret he said that he didn't have a girlfriend to leave behind. He said that he had had two girlfriends but neither relationship had come to anything. He didn't seem to be referring to longevity so I guessed he was referring to sexual activity. I told him that going to college was the perfect place to make new friends and develop new relationships. He looked very uncertain and I asked him why he was doubtful.

"All my friends have had long term girlfriends and they are confident around girls. I am afraid that girls at college will expect me to be more experienced... you know... "

"Do you mean that you are concerned that girls will realize that you are a virgin and that that would put them off?"

I realized that I had been rather blunt in voicing my assumption. He seemed unable to answer my question but this only strengthened my assumption. I went through all the arguments about why being a virgin was not a limitation but was in fact an advantage. I didn't believe any of them and wondered whether I sounded unconvincing. Changing my line I decided to try and build his confidence by complimenting his appearance. Stupidly I worded things as how attractive I found his big strong build and wonderful body. The good wine had slightly loosened my tongue.

He asked me when I had lost my virginity and I thought it diplomatic to lie and say that I had been a similar age as he was now. He asked me about my boyfriends and how quickly our relationships had turned physical. I wouldn't choose to admit all of the truth in this story and I certainly wasn't going to admit it to Pete. Pete clearly knew that I had just broken up from my boyfriend. He quizzed me why it had broken up and I said it was for the usual reasons. I explained these were usually down to money or sex. I had backed myself into a corner, as he wanted to know more, much more. He was a little quiet as he said,

"He must be blind and stupid to break up with you if it was because of sex. You are.... you are.... "

I couldn't believe that his words nearly reduced me to tears. This was completely out of the blue but had obviously hit a very raw nerve. I might have been a little slow but it suddenly hit me that the question he might be trying to ask me was to relieve him of his virginity. Had Judy set this up? She had certainly been very keen for me to consider Pete's request. She knew that my libido had always been extremely high and that I wasn't getting any action. Had she also set up the story of the water leak to ensure Pete and I had the full run of the house? It was hard to process all this but when I thought about sleeping with this stunning virgin the processing stopped abruptly. I had friends who kept a score of men they had slept with. I fully admit that when I ran out of fingers and toes to count them on I started counting only the virgins. It had been around seven years since the last one but I had not forgotten the intense excitement.

I didn't know what to say to this gorgeous young man as he watched my confusion. I would not have trusted my voice even if I had known what to say. I offered him both my hands and he took them to enable me to lead him, without a word, out of the lounge and up the stairs. My heart was beating out of my chest as it had done when I was a teenager anticipating having sex. I loved the way he stood in front of me looking scared but very aroused. Being just over five feet tall Pete loomed over me and I had to reach up to unbutton his shirt. He helped me by slipping in off his shoulders before standing up tall again. His chest was huge and as smooth as a baby's bottom. I had never experienced a totally hairless chest and his seemed to be radiant almost shiny. I wanted to lick it, kiss it and suck on his perky nipples. All this would have to wait until I had unpacked the real prize. I have to admit to loving the male organ, or as I always call them 'joysticks'. I had experienced many of them and enjoyed all of them except one or two attached to complete pricks. Pete's trousers were loose fitting but did little to dampen my enthusiasm as they tented out towards me. Impatiently I pulled his underwear down with his trousers. He was stepping out of them as I stood back waiting to enjoy the view. When he did finally straighten up I was delighted to see an erection that was more than in proportion to the rest of his huge frame. His pubic hair was very short jet black and tightly curled. I knew his cock was big but I didn't realize how big until I wrapped both my hands around it and still had two or three inches crying out to be taken in my mouth. I say my hands were wrapped round the monster but they did not go all the way round as it was too thick.

I had resisted taking the huge almost purple head into my mouth as I suspected my mouth would be quickly filled. I had decided that it was almost certainly better to ensure that Pete had his first orgasm before penetration took place but I was far from ready for it yet. My experience of virgins or very inexperienced lovers (a specialization of mine) was that they fell into two main categories. Firstly there were those that however they had their first orgasm they were happy with that or were unable to go again. The second were those that were much better lovers after they had cum the first time. I was hopeful and reasonably certain that Pete was in the second category.

"You have the most wonderful body and I want to enjoy it to the maximum but right now I would love it if you would undress me."

Between us I was naked in less than 30 seconds. It felt great as he seemed to love drinking in the sight of my body and his excitement was very obvious. My nipples had risen to the occasion and my pussy was moistening up nicely. We were still standing as I placed his fingers on my warm pussy. I used my fingers to show him how to rub my pussy and clit. He was enthusiastic but clearly not experienced. The enthusiasm was enough to get my motor running. His erection looked angry enough to explode without any assistance. I had enjoyed one lover who always experienced his first orgasm without either of us touching his joystick. I was much too excited about Pete's cock to allow this to happen. I wanted to slow things down so that we could both anticipate and enjoy his first orgasm with me.

He allowed me to take gentle control and we were soon lying naked next to each other on the big bed. With more experienced lovers I would have insisted that they went down on me so that I was not only ready to be fucked but was desperate for it. Given this particular situation: faced by a gorgeous young virgin with a huge joystick, me being very ready was never going to be a problem. I decided to give him a tour round the female body. He got the message immediately and explored every new part of my body with an enthusiasm that was intoxicating. He was gentle, rather too gentle at times as he ran his hands up towards my ass and my pussy. His caress of the cheeks of my ass felt wonderful. He seemed completely happy to play with them without trying to explore towards my very sensitive anus. He watched my reaction as he knelt to take both of my boobs and erect nipples in his hands. I nearly showed him how he could better arouse my nipples but decided to let him find out for himself. As much as I loved his inexperienced exploration I wanted him to find my now excited but rather neglected pussy. For the second time I not only guided his hands to my pussy but briefly showed his fingers ways to excite me. In this position his magnificent joystick was a joy to behold. I wanted to hold it, suck it, tease it and conquer it. I told him to lie back as I now wanted to explore his beautiful body. He seemed very happy with this. Close up his cock was simply stunning. The prospect of being penetrated by it was awesome but I knew it would be much more enjoyable for me if he didn't explode within seconds.

I wanted to play but suspected that he was already very close to losing control. I knelt next to him such that I could offer him a nipple to chew on. I love my nipples being played with when my boobs are hanging in this position. I reached down past his cock to hold his full firm balls. I wasn't sure whether it was because of his age or whether it was just the way he was built that they were fuller and firmer than any I had held for a very long time. His hips pushed up to increase the contact and possibly to try and bring my arm in contact with his shaft. After exploring his balls I held them in one hand as I ran a single finger the length of the vein that ran the length of his shaft. He shivered violently as I did this and I wondered if he was going to explode immediately. I wanted everything. I wanted to feel him explode as I sucked him. I wanted to see him cum as my hands played with his cock or balls. I wanted to know whether a touch of his ass would make him lose control. I had to choose one, as I knew he would not last long.

"Can I.... can I....?"

"Are you asking whether you can put your cock in my pussy, fuck me, the answer is yes I would like that? I think that if you did that right now it might be over rather quickly. Trust me I want you to fuck me as much as you want to fuck me. Let me just relieve the pressure in your balls so that we can both enjoy the fucking when you are a little less excitable."

There was a flash of disappointment before he realized that I was offering a win/win situation or more a cum/cum situation. Then the offer I was making him registered fully and his smile was beautiful. I knew then that of all the options available to me the one I wanted was very simple. I wanted to watch this boy with the beautiful cock loose all control as my hands did the work. I wanted to watch his face his body and this cock as he enjoyed an orgasm. I watched his face as one hand played with his balls and my other played with his cock. Both my hands were super gentle. He did reach between my legs and found my excited pussy with one of his hands. Studying him as I was, I knew he was going to cum at the same time, as he knew it. His balls tightened, his body tensed and when the first squirt starting passing through his rock-hard shaft I felt the force of it. The first rope was huge and hit the headboard above his head leaving a trail across his face and his whole body. He squirted half a dozen or more times with much less force but plenty of volume. Even then more oozed out as the tension left his body. The expressions on his face were a picture of helplessness, excitement, happiness and finally contentment. In that fleeting moment it was hard to imagine him enjoying any more sex for days.

Although I was still very excited there was a slight feeling of anti-climax as the monster cock softened to more normal dimensions. I felt happy for him and wanted to give him a cuddle. This however was not going to satisfy the fire that was burning throughout my body but particularly between my legs. I think I am strange as I love masturbating and giving head to men but am not a great lover of the cum they produce. Pete was covered in it so I was quite happy when he disappeared to the bathroom to tidy himself up. I was ready and eager to move to the next phase by the time he returned with a clean cock that was showing signs that he would need little encouragement. As inexperienced as he was someone or something had clearly suggested that oral sex was a good way to get a woman ready to be fucked. I returned to a kneeling position but now with my pussy hovering above his face as my mouth found the firm head of his cock. Even as far off fully erect as it was it required me to open my mouth wide. The silky skin felt wonderful against my tongue. He didn't need asking as he pulled my pussy down and his lips and tongue found their target. Being on top allowed me to maneuver myself to ensure I received maximum benefit from his enthusiastic efforts. As for my efforts to arouse the slightly sleepy giant I need not have worried. Oh what it must be like to be a teenage boy. His size was soon back to its impressive best but there was just a hint that he was not quite as hard as before. This allowed me to indulge myself without feeling guilty about teasing Pete. His bum cheeks felt great in my hands as I spread them and pushed them up to let me take as many inches of his cock into my mouth as I felt comfortable with. Now as I gently fucked him with my mouth I started to explore right to the heart of his cheeks. When I found the crinkled skin he drew in a deep breath but fell short of comment or protest. I certainly had his attention and the hardening of his cock told me more than any words could.

He was more than ready and as for me I was desperate to experience the penetration I had been fantasizing about since I had first laid eyes upon his joystick. We didn't need words to check that this was not only what we both wanted but also that we wanted it immediately. I was just a little nervous that I might find him too big to be comfortable and was therefore happy to be in control by remaining on top. My pussy was soaking but I did ensure that at least the head of his cock was suitably lubricated. Again we held each other's gaze as this time my lower lips were stretched beautifully before two or three inches pushed through the tight barrier. His face was a mixture or concern, relief and excitement as I felt ever ridge of his erection as it opened me up spectacularly. It took many gentle thrusts before his cock was able to visits places that had rarely and eventually never been visited before. Suddenly I remembered that this was not all about me. This was Pete's first time and as such I wanted to make it unforgettable for him. His body was tense as I took hold of his hands and brought them up to my boobs. Ridiculously I asked him if he was okay. This relaxed him and maybe me as we both laughed.

His hands played with my nipples as I fucked him firmly but not violently. His arousal was building and his hips started to match my thrusting. He was stretching me beautifully and I am sure he was repositioning half of my insides. I stopped moving letting him take over and set the pace. He let go of my boobs and gripped my hips thrusting up much more aggressively. It was exactly what I needed and almost straight away I knew nothing would stop me cumming. Now we fucked each other with a degree of abandonment that could never last long. It didn't as I screamed out that I wanted him to fuck me really hard. His inexperience was now not important. What were important were his urgent need and his huge cock. I felt like a rag doll being thrown around as my orgasm ripped through me and his ripped through him. I have had orgasms that have left me more satisfied but never ones that were as violent or as long lived. We were both exhausted when our bodies finally settled down. I collapsed forward with my head on his chest / shoulder and his arms held me tightly. It was still not late but a short doze together soon turned into settling down for the night. He wrapped his huge frame around me.

It was me that woke during the night from a happy dream that involved an alien with a huge cock. There was no alien around but a huge semi-erect cock was only inches away from where I wanted to feel it again. Pete was fast asleep but this only added to my excitement. I returned to the bed having raided his parents bedside unit in a successful search for lube. I was excited with a pussy ready for action but I was tender from the earlier action and knew that huge amounts of lube were going to be necessary if I was going to be comfortable being fucked again. I was determined to give him the best head I could. He either didn't wake or if he did he was happy to pretend he was still asleep for three or four minutes. I was happy either way.

It was a much more confident young man who finally woke and asked me what was my favorite sexual position. I joked "any position with a beautiful cock like yours in my pussy." I added that I loved rear entry before worrying that he would think I was asking for anal sex. I love anal sex but there was no way that his monster would ever fit up my ass. I explained that I found being fucked in the pussy from behind was great because penetration was deeper and it left my clit very accessible. As I started to explain this I realized that it was quite ridiculous given that deeper penetration was not exactly a top priority for Pete's partners. The scary idea of Pete deflowering a young student using rear entry flashed through my mind and I decided that showing him a position that was more virgin friendly was probably kinder.

I always think that the position I showed him was a very intimate one. I lay flat on my back and got him to lie on his side and back facing me so that he could enter me from under my bent legs. My back was not raised off the bed and while his legs were at 90 degrees to my body he was able to bend at the waist to lie alongside me. In this position we were both able to be relaxed and have access to most of each other's bodies. I talked to him about how I liked to have my boobs played with. He also spent time working on my clit. As wet and excited as I was the lube was a godsend. I was very thankful that the relaxed position allowed us to enjoy gentle fucking as lube or not I could have got sore very easily. This time it was slow lovemaking rather than just sex. I showed him how to excite my body with his hands and used mine on his gorgeous body. I didn't think I would climax again but I did slowly build and when he announced that he was going to explode I was only a few seconds behind him. It was not an exceptional orgasm but was very pleasant and we were both asleep within minutes. Pete and I shared an early shower. I was sore from the earlier activity but he was very keen for more action. We were both very happy for his beautiful cock to stretch my lips as I knelt in front of him. The head of his cock was big but I was just able to use my tongue to play with it. I was delighted when my hands felt his balls contract and his head expand just before he filled my mouth with his cum. Even after everything his cock was still heavy as I washed it and he washed my pussy.