4 comments/ 167814 views/ 68 favorites Ray's Tale / Tail By: Belgarion10 I first met Ray on holiday, but my 20 year old girlfriend Donna had known him for almost 15 years, since she was a little girl because he used to be one of her dad's best friends. Ray and her father weren't quite so close anymore, but he still dropped into Donna's house now and again, usually at Christmas time and birthdays. Donna hadn't seen him for several months when we ran into him, while we were on holiday in Spain. He was with his girlfriend, as he had separated from his wife sometime ago and when he recognized Donna he invited us to have a drink with him which we did. We spent the entire evening with them and we had a nice evening. We didn't see much of him for the remainder of the holiday apart from one day on the beach. He sat with us for a little while and we chatted and had a drink in the beach bar, but after a while he had to return to his girlfriend and after that we didn't see him at all until we returned to England. He dropped in to see Donna's dad a couple of weeks after the holiday, and mentioned to Donna as he was leaving that he and his girlfriend Anne were going out uptown that weekend if Donna and I wanted to meet up with them for a drink. Donna had got on really well with Anne, so he thought it might for nice for them both. So that weekend we all met up but unfortunately Anne couldn't make it. Ray was with a couple of his buddies instead and apologized for not letting us know, but told us that we were welcome to hang around with them for the night. It was a good night actually, we drifted from bar to bar and ended up in a nightclub dancing the night away. Ray's friends drifted off at the end of the night, leaving just the three of us waiting for a taxi. We were standing there for what felt like forever, so when a taxi did finally turn up Ray offered us to come and stay the night at his house. He was divorced and lived on his own at the moment as Anne wasn't ready to move in yet, so he had a guest room and a spare bed. Donna was okay with it and was freezing cold from waiting for so long for a cab, so we went with it. One of Ray's friends had been eying Donna up all night and flirting quite heavily with her even though she had made it quite obvious she wasn't interested because the guy was really fat - in fact he wasn't very good looking at all. However, I could tell that Donna quite fancied Ray as she was very responsive to his jokes and her body language made it even more obvious, especially as she became more and more drunk towards the end of the night. At first I thought it was because she was friends with him and had known him a long time, but by the end of the night it was clear that she had an attraction towards him. In the taxi, she leaned against him, putting her head on his shoulder as she said how tired she was. She had a thigh-length denim skirt on with a low cut cream-coloured top and I clearly saw Ray look down her top quite slyly as she lay against him. He also put his hand on her knee, but again I didn't really think much about it because of their almost uncle/niece relationship. When we got back to Ray's house though, things changed pretty quickly. As if Donna wasn't drunk enough already, Ray brought us some more drinks and as we lounged around in his front room, the conversation turned to sex - as it always does when you have that potent mix of men plus women plus alcohol. At first we were talking about the holiday but then Ray commented on how good Donna had looked in her bikini on the beach and how she had grown into a fine looking woman since he had first known her as a little girl. Donna was blushing but obviously enjoying the attention. I should point out that at this stage, Donna had been with a couple of other guys besides me, but we weren't in anything remotely resembling a 'swinging lifestyle' or even an open relationship. Donna had had a little affair with her boss at a shop, which I had found out about. When she realized that the thought of her with someone else had turned me on, she had slept with a buddy of mine after a drunken night out, which was the first time I got see her with someone else. Then after that, she screwed an old boyfriend from school who she had never got to sleep with back when she was going out him. Both those times were one-offs and hadn't been particularly memorable, or as good as her initial affair. Despite these little affairs we were still really in love, so I really never expected anything to happen that night with Ray. But it did. Ray revealed to us that he used to be really envious of Donna's father, because when he was younger he used to fancy her mother. Donna thought this was hilarious but her attitude changed when he told Donna how much she looked like a younger version of her mum. I should probably explain what Donna looks like at this point. She is an English rose type, with straight dark hair to just past her shoulders, pale skin and bright blue eyes completing an innocent looking and very pretty face. She is just over five feet tall and very petite with 34B breasts and a lovely figure. Donna's figure was very similar to her mother's, roughly the same height and build, but Ray said that he thought that from what he saw on the beach, Donna probably had a slightly better body. Then it all went weird. I was in Ray's kitchen getting another beer from his fridge when he wandered in to talk to me. "I bet Donna is really great in bed?" he asked, quite casually, and that's how we ended up talking about sex for the rest of the night. We both walked back into the living room and the conversation carried on from there. Ray was trying to embarrass Donna by saying things like "Paul tells me you're a great fuck," along with other dirty things like that but Donna just kept giggling as he got more and more suggestive. The conversation swung to mainly Ray bragging about his various conquests, which was obviously the reason why his marriage had failed. After a little while I went for more drinks and a toilet break and when I returned Ray was shirtless. Even though Ray was a much older guy, in his late 40s, he was really buff. Quite tall, very muscular and tanned, Ray was certainly a good-looking guy, regardless of age. Donna was now sitting with Ray, and she was feeling his chest and biceps as he flexed his muscles for her, giggling like a little girl as she did so. Donna was only nineteen and wasn't all that mature even for that age. She was complimenting him on his body and I saw his hand drop onto her leg and begin stroking up and down her thigh. As they leaned in close to each other I thought "They're going to kiss" and started to wonder what the hell was going on, seeing as they had this avuncular relationship. They didn't kiss though. At least not just then. I was drunk and really tired and when I said so, Ray got up and showed us to the spare bedroom. I got undressed and climbed into bed. Donna stripped to her black bra and knickers and joined me, but after a few minutes she said she needed to go pee and skipped out of the room. I lay on my own there for a little while before hearing voices from the landing which I went to investigate. Donna was standing at the doorway to the bathroom in her just her underwear, talking to Ray who was washing his face in the sink. He was just wearing a tight pair of briefs and his package was quite prominent. He looked huge, almost like he had something stuffed down there. Seeing them standing semi-naked right next to each other, I think it was then I realized that something might be about to happen. Feeling a bit inadequate I put my trousers back on and when I came back out of the guest room, Donna was following Ray into the other bedroom. I decided to give them a little time to get friendly and went downstairs for another drink. When I did return things hadn't progressed as far as I thought they might but they were progressing. I heard music and peeked my head around the door to see them both sitting upright on the bed, leaning against the headboard, both still in their underwear. Ray had his arm around her shoulder and Donna had one of her legs hooked over his. They looked very comfortable together and when they saw me Ray told me to go get them both a drink and I could join them. There was a chaise lounge next to the bed so when I came back I flopped out on that and enjoyed listening to some CDs with them for a little while. It was warm in Ray's house and I was very relaxed and dozing in and out of sleep. Both of Donna's bra straps had fallen off her shoulders, so she was displaying a good amount of her modest breasts without any of her pink nipple or aureola actually coming into view. I found that quite arousing, my relatively inexperienced, pretty and petite nineteen year old girlfriend almost completely exposed in front of the imposing, very masculine and much older Ray. They were still talking about sex and Ray was still showing off while he did so. Donna's hands kept rubbing his chest muscles or his arms or thighs as they spoke. I could tell she was feeling a little horny. It was the silly little things that turned me on like Donna pulling her bra straps up over shoulders, only for Ray to slip them back off, making her giggle. Ray's arm was still around her shoulder, and the hand that dangled down would sometimes stroke the upper part of her breast as they talked, and occasionally the other hand would drift over to her thigh, sliding up towards her groin but never actually straying too far. The situation was like a bomb - armed and ready to explode. It just needed someone to prime it, so I lit the fuse. I waited for an opportunity in the conversation and then joined in with a little revelation about my seemingly innocent girlfriend. Ray was saying something about he liked slutty women, so I piped in that Donna could be slutty when she wanted to. I saw Donna's eyes widen but I carried on and explained to Ray that she wasn't as naive as she appeared. I told him briefly about her little affair with her boss and how I had also shared her with a friend after a drunken night out. Ray looked at Donna with a slightly surprised expression, but she only shrugged and took a long swig of the drink I had brought her. Ray asked if he was in with a chance tonight, in a joking type of way and Donna replied teasingly "Maybe," with a naughty smile. Ray seemed to get really excited at that and looked at me for encouragement. I waved at him to go ahead and that was the start of it. The hand that was around Donna's shoulder slipped south and into Donna's bra, feeling her breast and she did nothing to stop him as he asked her if it was true what I had said. Donna nodded dumbly as he pushed her bra down a little, bringing her breasts fully into view for the first time. Donna's breasts were smallish - a 34B - but they were lovely and firm and perfectly shaped, pert and high with medium sized pale pink nipples. They kept talking as I lay there watching with my eyes half-closed. The hand that Ray had been rubbing up and down Donna's leg was now finally straying across the crotch of her black panties, gently stroking and rubbing her mound. Ray had earlier been bragging that he was well-endowed but he warned Donna that his cock was really big and that she should be careful, but all that did was to provoke Donna into slipping a hand down his ridged belly and into his pants. As she did that Ray did the same with his hand, pushing it under the waistband of her panties and down to her pussy. After a few moments I saw Donna's eyes widen again and she muttered something along the lines of "What the?" as she felt the size of his penis. As Ray laughed gently, Donna pulled his pants down and the biggest cock I had ever seen popped out into view. I had never seen anything like it. With my beer-addled eyes it seemed like it was as long and as thick as my forearm, but Ray gave me the exact size when he answered Donna's question as to his size and told her it was nine inches long. "It's a real cock that, isn't it?" he said. Donna just nodded as she took it in her hand, which only covered half of the length of the shaft. I was still stunned. I had only seen the likes before in porn movies, and to see something like that in reality was difficult to believe. His dick was hardening rapidly as Donna started to slide her hand up and down. It was much thicker along the shaft, fatter in the middle and drawing to a point almost at the end. Her fingers barely fitted all the way around it at its thickest point. She waved it around and leaned forward to look at it closer. While she held it pointing upwards towards the ceiling, Ray moved his hands behind her and expertly unclasped her bra. I don't even think Donna noticed it as it fell away, so distracted was she at the thing she held in her hand. Her pert little breasts fell free and wobbled slightly as she tugged up and down on Ray's now massive cock. Donna looked over at me with an incredulous expression on her face as she stroked Ray's giant manhood. I smiled at her and she turned her attention back to Ray. At that moment, if I had touched myself I would have cum myself. I was that horny watching the scene unfolding in front of me. Donna gasped that it was "massive" and then shifted her position on the bed, so that unfortunately her back blocked my view and I must have gently dozed off with the copious amounts of alcohol I had consumed because the next time I looked over at them, a now completely naked Ray was sitting opposite my topless girlfriend. She was still playing with his erection as he reached a hand forward to pull down the front of her panties and then his head ducked to look down at her dark, hairy bush. Because she was dark-haired, her pubic hair was dark and thick, making it difficult for her to shave completely, so she would just trim it into a neat and tidy triangle. Something was said which I couldn't hear and there was some giggling and laughter between them but Donna didn't resist as he tugged down her panties, slipping them off her feet and making them both naked. I knew he was going to fuck her then and I was intrigued at what exactly would happen, so I just sat there on the chaise lounge and watched. Donna laid back on the bed with her legs apart and Ray lay down on his side next to her. They were talking quietly to each other and Ray's hand casually slid down her body, stroking first her nipples before moving down over her flat stomach to her hairy pussy. Ray asked her how many cocks 'this' had had inside it, while he stroked her labia and clit, making Donna tremble slightly and when she replied 'a few' he asked her if it had one as big as 'this,' indicating to his now fully-erect cock. Donna didn't speak, she just shook her head. They started to kiss and as Ray began to finger her, I noticed how Donna's leg, the one nearest me, was shaking, presumably with excitement though it may have been with nervousness. They kissed and played with each other for a while and then Ray made me jump when he suddenly sat up and rolled over, swinging his legs off the bed to sit up right in front of me. It was a while since he had last spoken to me, in fact I thought he had forgotten about me but he obviously hadn't. "She wants fucking, mate," he said, "Do you want to make yourself scarce for a bit?" I nodded. The guy was just such a presence that I felt a little intimated by his confidence. The way he was sitting upright, but resting back on his arms made his huge cock stand straight upwards. I recall looking at how far up his abdomen it sat, the tip resting a good inch or so above his belly button. I snatched my eyes away before he thought I was gay for looking. As I got up and left Ray suggested I go to bed in the spare room as I looked tired. I walked out, looking over my shoulder at Donna. She was still laid on her back and her eyes followed me as I left but she didn't say a word. I pulled the door shut, leaving it slightly ajar deliberately. I thought Ray might get up and close it properly so I didn't wait around on the landing outside. I went into the bedroom and climbed under the duvet. Ray was right, I was tired but there was no way I could sleep knowing that my girlfriend was going to be having sex in the room next door. Especially with that monster of a cock. I lay there in the dark for a little while, straining my ears to try and hear something from the adjacent bedroom. At first I only heard quiet voices and giggles but within a short time the noises disappeared, apart from a creaking sound, which I presumed to be their bed. When I heard Donna begin to moan, I decided to find out if I had left the door open enough to see what they were doing. I climbed out of bed and still wearing only my boxer shorts I walked across the landing towards the bathroom, so I could pretend I was going to pee should I get caught. Luckily I had left the door ajar just enough to see inside, so on my way past I peeked through the gap and saw Tony on top of Donna, grinding slowly between her legs which were wrapped around his back. The sight was entrancing and I stood there watching for a little while before Ray suddenly got up off the bed, causing me to dash into the bathroom. I made myself have a pee, and when I finished Ray was waiting outside the door, stark naked. His erection had wilted, his dick still longer than mine even when soft, and I felt a bit of disappointment that he had cum so quickly. I had been enjoying watching my little girlfriend with this huge guy. Ray didn't say anything as he walked past me into the bathroom, and when the door closed I entered the bedroom where Donna was still laying on the bed. Her legs were still open slightly, enough for me to see how wet she was. Her pussy lips were pink and puffy and her pubes were wet and sticky but I couldn't tell if it was with cum or just sweat. Her face and upper chest were flushed pink with excitement as I sat next to her on the bed and asked her if she was enjoying herself. Her eyes opened to look at me but before she could reply they moved past me to look at Ray who had stepped back into the room. He was stroking his cock back to erection again and when he saw me, he motioned with his hand to move. "You can have your turn in bit mate," he told me. "I haven't finished with her yet." "I thought you'd done?" I said as I shifted back to the chaise lounge. Ray just smiled and explained that he'd only gone to the toilet for a piss. "I'm no five minute wonder," he laughed, "I haven't cum yet, although she has, haven't you?" Donna just stared dumbly at him as he got back between her legs and with one hand, he slipped his cock into her again. Donna's legs resumed their previous position behind his back and they began to kiss as Ray's buttocks began to lift and pump into my girlfriend once more. This time Ray didn't tell me to get out or anything, and I tried to remain as invisible and quiet as possible, so they might forget I was there. Donna face was the wrong side of Ray's head from me, so I couldn't see her face but I could hear her gasping when Ray pushed himself right into her. After a short while, Ray lifted himself up, and quite roughly turned Donna over on to her front. He moved her legs apart and lay back down on top of her to fuck her from behind. Donna grunted as his pumps became more urgent and when he pulled her up onto all fours, she let out a deep animal groan as he shoved himself fully into her so that his groin thudded against her backside with every thrust. I watched them in silence, the only noise in the room was the slap-slap-slap of Ray's balls against Donna's pussy and her increasing grunts as Ray drove his full length in and out of her. Before too long, Donna's breaths grew closer together and finally her back arched, her dark hair falling back as her head raised upwards and she screamed out loud and came. Ray held his hands on her shoulders, impaling her right onto him until her orgasm subsided and her muscles relaxed. Donna tried to flop forwards onto the bed, looking exhausted, but Ray pulled her back towards him. Ray's Tale / Tail "No, you don't. It's my turn now." He looked at me. "Don't worry mate," he said, "I haven't got anything," and he shoved himself back into her. This time there wasn't any finesse or anything, he just savagely pounded her from behind, bringing yet more groans and grunts as he manhandled my pretty, petite girlfriend. Sweat was dripping off her face, and her facial expression was screwed up in a mixture of pain and pleasure. I really wanted to tell him to not cum inside her because I wanted to fuck her afterwards and I didn't fancy screwing a pussy full of another man's cum. However, it was too late. Ray hammered into Donna one last time and shouted "Oh fuck!" as he shot his load into her. When he finally released his grip on her hips, Donna slumped onto the bed, looking tired and maybe a little relieved. "Your turn now kid," Ray said with an arrogant smile as he wandered out of the room to clean himself up. I looked at my girlfriend, and she must have felt my stare because she opened her eyes and smiled rather weakly at me. I asked her again if she enjoyed that and she nodded dreamily. I was absolutely dying to cum, and so I began to unbuckle my jeans to see how Donna would react. She just looked at me and smiled, so I quickly dropped my jeans and shorts and as Donna rolled on to her back and opened her legs I practically dived on top of her. It was quite a shock at first, how wet she was. Her pussy felt cool and slimy with Ray's cum, and she also felt quite loose which wasn't surprising considering the size of the tool which had been ramming her just a few minutes before. Ray was a hard act to follow, so I had to give it to her as hard as I could, even though I knew I wouldn't last long. Just as I started to screw her, Ray walked back into the room. "Go on then sonny," he said in encouragement, patting me on the back as he walked past. My concentration broken for a moment, I looked over at Ray as he sat down on the chaise lounge where I had been a few minutes ago. He was still naked but had a fresh can of beer in his hand. His dick hung down between his legs, flaccid now but still bigger than mine was when fully erect. When he saw me looking, he urged me to get on with it. "Are you going to fuck the girl, or what?" I resumed pumping into Donna as hard as I could, and felt her hands on my arse, pulling me deeper into her, though I couldn't hope to go anywhere near as deep as Ray. When I first started screwing Donna I was close to cumming, but with Ray watching I was finding it hard to reach orgasm. I kept pumping as hard as I could, but after several minutes I started to tire. Ray saw me flagging, and egged me on further. "Come on kid, give it to her properly!" I was low on energy, so I broke away for a second and moved Donna onto her hands and knees, using the time to also take a breather. After a few moments, I re-entered her from behind and started to screw her, but Ray butted in again, just as I started to find a rhythm. "You're never going to make her cum like that," he laughed at me, "Fuck her properly!" I couldn't believe he was laughing at me! The smirk on his face had a really strong effect, eliciting both anger and humiliation and yet at the same time in a strange way it seemed to turn me on. I really was screwing her as hard as I could, during which time Ray watched us, chuckling under his breath and shaking his head at my efforts. I sort of gave up and let myself cum. Ray had already spunked inside her, so I could have let myself shoot inside her but I preferred to pull out and cum on her backside so I did. Donna complained that she didn't want me to stop, moaning that she hadn't cum yet and I apologized, but she wasn't happy. I was quite offended and embarrassed by this, as it made me look a bit useless in front of Ray who was already laughing at me anyway. Again, this humiliation had the unexpected effect of turning me on somewhat as I went to the bathroom to clean up. I was feeling really tired now, despite splashing some cold water on my face, and I went back into the bedroom intending to collect Donna and go to bed to get some sleep. Donna had other plans however. Ray was sitting on the chaise lounge still where he was when I had left. But now Donna was kneeling on the floor between his feet, sucking his cock back to hardness. Ray looked at me and explained that she needed finishing off because I hadn't done the job properly. He had told Donna that if she got him hard again he would sort her out for me. I got dressed, watching her work on his cock for a few minutes until Ray got hard again. He didn't screw her straight away though, he grabbed her head by the hair and started to fuck her face quite roughly. I looked at Donna, slightly concerned for her but she actually seemed to be enjoying the rough treatment. She was whimpering moans of pleasure as he pulled her head up and down on his cock, so I didn't object to what he was doing. I just walked away, unable to watch anymore. A mixture of tiredness and resignation that I couldn't fulfil her needs like Ray could led me out into the other bedroom, where I laid down and fell asleep almost instantly. I wasn't sure how long I had been asleep when I was awoken by a banging noise and Donna moaning loudly. I listened for a little while, trying to go back to sleep but the noise only got louder and Donna was almost screaming, so I went back to the landing and looked through the door once more. Ray had Donna on her back near the edge of the bed. He was stood up, holding her legs spread obscenely wide, his hands around her ankles while he fucked her hard and fast. Donna's hands were gripping the bed sheets and she had a wanton look of passion on her face that I had never seen before. The headboard of the bed was thumping against the wall as he hammered into her, his stamina seeming unending. "Yes! Fuck me! Oh god, fuck me! Fuck me!" Donna growled at him in lustful tones and Ray obliged, drilling into her so that his groin banged against hers noisily. I watched silently until Donna came, her back arching as she wailed with her orgasm while Ray just kept pumping into her, and then I went back to the bed to try and get some sleep. The banging continued for a few minutes and then I heard Ray call out as he came. Finally silence returned and I slept the rest of the night through without waking. The following morning, I awoke alone and wandered into the bedroom where Donna and Ray were asleep together, under the blankets. I woke them both up and asked if they would like a coffee or anything, to which they both replied that would be great. When I returned back upstairs with a tray full of coffee mugs, they were at it again, this time in the spoons position under the covers. I was really hung over and felt quite ill, certainly not in any state to join in, so I left their coffees by the bed. Donna looked at me as I set the coffee down and mouthed the word 'Sorry' to me. I smiled at her and said it was okay then left. I went to the bathroom and had a quick shower and when I came back they were almost finished. The covers were thrown off the bed, and Ray was screwing her doggy style again. Donna looked at me where I was standing in the doorway as I watched them. "I'm sorry," she said again to me as Ray screwed her from behind. He was fucking her much slower and less rough than last night, probably because like me they felt delicate and fragile from all the alcohol we had consumed last night. She looked over her shoulder at Ray and sighed in pleasure, closing her eyes as she did so. "Fuck me," she said to him, "Oh god, yes, fuck me." She turned back to me. "I'm so sorry, it just feels so good." While he wasn't doing her as hard, Ray was screwing her steadily, pushing his full nine-inch length in and out of her. "Come here," Donna beckoned to me and as I walked up to her, she unbuttoned my jeans and pulled my cock out of my shorts. Ray carried on screwing her as she took me in her mouth and started to suck me. I got hard almost straightaway which surprised me considering my hangover state, and as I looked down at Donna I noticed that there was dried cum not only on her back, which was from me, but in her hair and on her face and cheek. It didn't take me long to cum, right in her mouth, which she swallowed down without comment and almost immediately afterwards Ray sped up his thrusts and came inside her pussy again. Without any further ado, he announced he was going in the shower. "She's a good fuck, your girlfriend," he said to me as he downed his coffee. "You want to hang on to her, mate." He left me and Donna alone and went to shower. I looked at her, laid there getting her breath back. "Did you enjoy that?" I asked her and she nodded, then started to apologize again, but I silenced her with a kiss. "It was so amazing watching you," I told her. "I can't believe you took his... thing. It's massive." "I know," Donna grinned, then admitted that she had been a bit scared the first time she saw it but once he managed to get it in, fear gave way to pleasure. She confessed that they had been at it all night, in fact she had lost count of how many times he had fucked her through the night. At one point she had woken up to find him on top of her, trying to get his cock in her once more while she was asleep. Maybe it was because Ray was an old family friend, or maybe he was just skilled at this sort of thing but there wasn't any awkwardness afterwards. He made us breakfast, and then in his relaxed manner he asked Donna if she might want to make this a regular thing. Donna surprised me by being equally at ease with her answer, telling him that she would love to but that it was up to me. I told them both that she could do whatever she wanted to - I didn't mind at all, in fact I had thoroughly enjoyed myself as well last night. So that was the start of it - Donna met up with Ray fairly regularly after that, once a week or sometimes every fortnight. It started with her going up to his house on a Monday night for a couple of hours, but then it turned into her staying overnight. Her family thought she was staying with me, but really she was getting a hard fucking by one of her dad's best friends! And that was why it ended. Ray suddenly decided that he felt uncomfortable sleeping with her because of that reason. It seemed a bit strange to me because he had been screwing her regularly for a couple of months when his guilty conscience suddenly kicked in, so I think the reason was really that he had got a bit bored, and probably had a new bit of stuff to start stuffing instead! Donna and I lasted for several more years, but from that day with Ray onwards, she never quite looked at me in the same way. She had become a bit of a slut for men with big cocks, and with my average endowment I just couldn't cut the mustard anymore. I know Ray eventually married Anna, and that Donna was cheeky enough to go to the wedding. I think she was jealous! I'm now married to a beautiful woman, and while I would love to see her in action with another guy I would never let her near a guy as well hung as Ray. Be careful what you let your girlfriend get up to!