Perhaps I should not have shown Jimmy the pictures, or perhaps having done so, I should not have told Ruth. That said, I had and I did. I wasn’t even thinking about that as the three of us sat on my bed, me with my back against the headboard, Ruth leaning back against me, and Jimmy facing us from the foot of the bed. I wasn’t thinking of it, but as it turns out, she most definitely was.
Ruth and I had a long distance relationship. She lived in Colorado, and I in a small town in Texas. We had met when she was visiting friends in my hometown. She had just turned 16 when we met, and I was 19.
I thought she was the most sensual, sultry, and sexy girl I had ever met. If it is true that a person can exude sex, she is that person. I, on the other hand, was extremely shy around girls, and had just had a bad break-up with a girlfriend. Ruth left me tongue-tied, and she knew it, and it seemed to amuse her. We started writing after she went back home, and calling each other on the phone. Her candid and straightforward attitude relaxed me and we shared a lot of our life experiences and fantasies. I learned the sexuality she exuded was not a tease or an act. For Ruth, sex was a casual thing that was enjoyable. If you are thinking slut I suppose you could be right, but that’s not a complete picture.
The pictures. A few months before I had visited Ruth in Colorado, and one day we had driven up into the mountains to visit some of the old mining towns. On the way back, we pulled off at a wide spot to look at the scenery and the river running beside the road. We walked down to the river and I took some pictures of Ruth standing on the rocks. She kept changing poses and the next thing I knew, she had rolled her tube top down to her waist. I was staring at the most perfect set of breasts I had ever seen. Okay, I had not seen many unless you count penthouse magazine, but these were perfect. I continued to snap away and she slowly peeled out of her clothes and there I was, taking pictures of perfection. She seemed totally comfortable being naked outside, and oblivious to the cars that would come by occasionally. I took in everything and snapped off pictures as fast as I could before she came to her senses. The roll ended and she picked up her clothes and walked naked to the car, riding nude until we got to her street, when she finally put her clothes back on. For the rest of my visit, I would find every opportunity to take more nudes of her, including some rather graphic pictures of her using her mother’s vibrator.
When I went to get the pictures developed, I was scared to death. I imagined the police screeching to a halt in front of our house and taking me away for trying to get obscene pictures developed. When the pictures came back and nothing was said, I was relieved and excited. Jimmy was my best friend, and somehow it seemed to be a good idea to show him the pictures of the girl from Colorado. Sitting on the bed, I had my arms around Ruth’s waist. We were all talking about something, but I can’t recall what. That’s when Ruth put her hands over mine and raised them so that I was holding her breasts.
I imagine the look on my face was pretty much the same as I was seeing on Jimmy’s face. It occurred to me that Ruth was wearing the exact same clothes as from that day in the mountains, and that it wasn’t a coincidence. Whatever conversation we were having came to a halt as I sat there with my hands on her breasts. I did what any young male would do, and begin to play with her breasts through her tube top. I couldn’t see Ruth’s face, but I could imagine the corners of her lips being turned up slightly and that confident look of sexuality she always seemed to have.
‘Do you want to see them for real’’ she asked, and I knew it wasn’t directed at me. I could see Jimmy nodding, and I felt her hands come over the top of mine and she pushed my hands and her top down to her waist together. ‘Don’t be shy, you can touch them if you like.’ Jimmy scooted closer and had his hands on her breasts in a flash. He put his thumb and forefinger around her nipples and squeezed her breasts with his hands while pinching her nipples. Ruth jumped and let out a gasp at his heavy-handed handling. ‘Sorry’, Jimmy mumbled. ‘No!’ Ruth replied, ‘I liked it, it just surprised me. Most boys try to be gentle. I like it better to have them worked over hard. You should see how hard I pinch when I’m getting myself off. Don’t worry about it. Be a man and show me how a man treats a girl’s boobs.’
That comment kind of nicked at me. I had always tried to be gentle and loving with her, and she had never complained or suggested I do otherwise. Plus, she was giving my best friend permission to continue mauling her breasts and implying she would enjoy it very much. There seemed nothing I could do about it, and Jimmy seemed more than happy to work her breasts over. I sat there with her leaning against me as she jerked, gasped, and moaned as he pinched and twisted her nipples and breasts for about 5 minutes. Ruth was breathing hard when he finally took his hands away. She made no attempt to cover up, but why would she’ She reached over her shoulder and directed my face to hers as she turned to me and kissed me before turning back to face Jimmy. ‘My turn, ‘ she said, ‘I’ve shown you mine, now show me yours.’
Jimmy looked uncertain, and then he smiled and lifted his shirt. I had to smile, and Ruth couldn’t help but giggle. ‘Okay, smart guy.’ I felt her moving and soon her fingers had her jeans unzipped and they, along with her panties, were sliding down her legs. Now naked, except for the tube top around her waist, Ruth leaned back into me and drew her knees slowly up to her chin before letting them fall to the side. I couldn’t see from my vantage point, but Jimmy was getting an eyeful and I knew exactly what he was seeing. Ruth had what I considered a perfect pussy.
Her pubic hair was naturally sparse, so the view Jimmy was getting was practically unimpeded. He seemed mesmerized, and started to reach his hand forward, only to have her legs snap together, catching it before he was able to reach his goal. ‘Uh-uh. If you want to touch mine, you have to let me see yours.’ I felt like I was a step behind. My girlfriend was naked in front of my best friend, had just let him have his way with her breasts, and was now demanding to see his cock. My heart was racing. Maybe if I had been thinking, I would have thought to put a stop to this before it went further. Maybe if I was thinking the word ‘touch’ would have jumped out at me. But I wasn’t thinking. I wasn’t going to object, and she knew I wasn’t going to object.
First, I’m just not that aggressive. Second, I had shared with her the rather embarrassing facts that even before I had had a serious girlfriend, one of the fantasies I had masturbated to the most were about my girlfriend fucking others. Third, I had told her I had found out a previous girlfriend had in fact cheated on me, and though I broke up with her, I had often masturbated thinking about her cheating on me. So, no, I wasn’t going to stop her. Jimmy hesitated not at all. HE hadn’t missed the word touch. He stood up and dropped his pants and there it was. To no ones surprise, he was rock hard. Ruth said, ‘Tim, changes places with Jimmy.’
I was on autopilot as I slid down to the foot of the bed, but did get a chuckle out of watching Jimmy try to maneuver with his pants around his knees. After a bit of struggle he was sitting against the headboard. Ruth had maneuvered herself around so that she was kneeling on the bed, facing him. She reached out her hand and wrapped her fingers around his cock, giving it a couple of strokes, bringing a small flow of pre-cum up to the head. After rubbing the pre-cum into his head, Ruth raised up off her haunches. ‘Okay, BIG boy, you’ve earned it. Touch whatever you want.’ I saw Jimmy’s hand snake between her legs and his fingers start to explore her pussy. I was not at all surprised by the wetness that drenched his fingers. I don’t think to this day, all these years later, that there has ever been a time I touched that pussy and didn’t find it slippery and wet. The girl just didn’t seem to have an off switch.
Jimmy continued to finger Ruth, and she stroked his cock slowly and firmly. Every now and then she would gasp or give him a word of encouragement. I don’t know how long this went on before I heard a soft moan and saw her shudder. It was a sound I knew well. My girlfriend had just cum on my best friend’s fingers. After a few more seconds, Ruth did a little spin, throwing her leg over Jimmy’s middle. She was now facing me with her pussy above Jimmy’s cock. The look on her face was a pure, sultry, lust as she slowly slid down, enveloping his cock in her soft wetness.
When she bottomed out, there was nothing to seen from my vantage point except Jimmy’s balls nestled against Ruth’s soft pubic hair. It was Jimmy’s turn to moan, and he did. Ruth just sat there, though I knew she was not really just sitting there. From experience, I knew she was flexing her muscles on Jimmy’s cock. Once Ruth was sure I wasn’t going to interrupt, she started fucking herself on Jimmy’s cock, raising herself up and down in a slow, methodical, rhythm. After a few pumps up and down Ruth rose up so that just the head was still between her pussy lips. ‘Look how big it is, Tim. It goes so deep and feels so good.’ She wasn’t saying it outright, but the implication was there. She was touching on my vulnerability. I’m just not that big.
I had read the research and I had measured myself and I knew I was smaller than average at 4’ inches. Still, I had never had complaints, and certainly not from her. Our sex was great. When it was clear to her I understood what she was saying and was not going to object, she started riding his cock again. I have to admit I was enjoying the show. After all, I was essentially watching a live sex show. When Ruth suggested it would be okay for me to take off all my clothes and jerk off watching them, I did without hesitation. I could have just unzipped and pulled it out, but honestly it never occurred to me. Ruth said get naked, and I did. After a few minutes of watching me jerk off while I watched her riding Jimmy’s cock, Ruth giggled and pulled off of Jimmy, leaning over to the nightstand and grabbing a pen. She straddled Jimmy, this time sitting with his cock in front of her and holding it against her belly. With the pen she drew a line on her belly. Hopping off, she crawled the short distance to the foot of the bed and pushed me back and straddled me the same way. I felt the pen against the head of my cock, but couldn’t see a thing. Ruth held her hand over he belly when she went back to Jimmy and kept it there as she positioned herself over him and slid down to the balls once again. Then she moved her hand to reveal what I knew would be there, two lines.
They seemed very far apart. She pointed to the lower one. ‘This is you.’ And then to the higher one. ‘And this is Jimmy.’ Leaning over to the nightstand again, this time without coming off his cock, she grabbed a ruler. Sitting back up, she positioned it against her belly. ‘Look for me and tell me how much difference there is’ By this point, I was no longer thinking, I was just doing what she told me to do. I leaned forward and as I did so her hand went to the back of my head, pulling me forward so that my face was inches away from where they were joined, and I was on my hands and knees. I felt extremely vulnerable, but I didn’t know why exactly. The two marks were exactly 3 1/8 inches apart and I said so. Ruth made me repeat it, louder, and then let me sit back down. Now it was time for the next act, it seems. Ruth twisted around so that she was facing Jimmy. I saw his hands go to her breasts, and I watched her ass pump up and down. ‘You know what I would love’ I haven’t had it in a long time. Jimmy, would you put me on my back, spread me wide and pound the shit out of my pussy’’
He wasn’t going to say no, and quickly they flipped over. After a moment to adjust, Jimmy was fucking her pussy hard and fast. ‘Don’t hold back. Slam fuck me. Hard as you can and even harder than that’ Jimmy obliged and pretty soon it looked like he was using everything he had to slam his cock home. The sound they made was more like the crack of a whip than a slapping sound. Ruth was making noises I had never heard, which is understandable since I had never dreamed of doing what Jimmy was doing. She started a chant of ‘Fuck me’ and he did. I had stopped jerking off. My cock was still hard as a rock, but I could do nothing but watch the blur of Jimmy’s cock sliding in and out of Ruth’s pussy. ‘I’m going to come!’ Jimmy said, and Ruth grabbed hold of his butt. ‘Cum inside me!’ Ruth screamed, and Jimmy let go with a loud groan that matched one coming from Ruth.
It felt like time stopped as they held that pose, with Jimmy pressed to the balls in Ruth, her legs splayed out as wide as they could be and both of them groaning through an epic orgasm. The whole image is burned into my brain still today, including the way Jimmy’s balls twitched as he emptied himself in my girlfriend. I had never fucked a girl like that, and I was pretty sure neither had Jimmy. After what seemed like forever had passed, Jimmy sort of collapsed on top of Ruth, and she stroked his back lightly while they kissed and cuddled. ‘You have to promise me something’, Ruth said, ‘Next time you will fuck me exactly like that, but in my ass.’ Jimmy quickly promised. Of course he would. Who wouldn’t’ I was shocked. Anal sex had come up in our sex talk, but Ruth had always seemed indifferent to it. At this point, things could have become uncomfortable. The sex was over, and rational thought was returning. Jimmy reluctantly rolled off of Ruth and pulled up his pants. ‘I reckon I should get home.’ he said. There really wasn’t anything else for him to say, and he left. There was lots for us to say. Ruth asked, ‘Are you okay’’ ‘Um. I think so. Not sure I will be later, but right now I guess I am.’ was all I could say. ‘You know I love you, baby.’ Ruth said. ‘It was just sex and I know it was your fantasy too.’ I couldn’t argue with that. ‘Was it as good as it sounded’’ ‘Oh my god it was amazing. Best sex I’ve had in months.
She must have noticed the wounded look on my face. ‘Baby, don’t be hurt. I love making love to you. This doesn’t change that. It’s like running. Some people are faster than others. Some people fuck better than others. Jimmy’s bigger and fucks better than you. I’m not being mean; it’s just the truth. Doesn’t mean you don’t do me good. It only means he does me better.’ Again, wasn’t much I could argue with. ‘What did you mean by next time, and since when do you want anal sex’’ ‘If you tell me no, then there won’t be a next time. But I do want to fuck him again if you will let me. Anal, that’s different. There’s this place. I don’t know how to explain it. If a guy is big enough to reach the place, then anal is the best sex of all. If he isn’t, then it’s just uncomfortable. Sorry, baby.’
As you can see, Ruth had a way of saying things that left no room to argue. I slid up next to her and cuddled her. If my cock had wilted at all, the touch of her skin brought it to full hardness. ‘So is it my turn now’’ She smiled, ‘Baby, my pussy needs a break after that pounding, but I would love for you to eat me right now.’ ‘But Jimmy just shot a load in you.’ ‘Don’t be a baby. Please’ I really need a soothing tongue down there. Its not like you haven’t eaten sperm before. She had to remind me. Another of my dark secrets I had told her. ‘Please baby’ Will you please go down there and eat all of Jimmy’s sperm out of my pussy’’
Like I said, there’s really no arguing with her. I slid down between her legs and used my tongue on her well-fucked pussy. As I lapped up the load and her juices she giggled softly. When I felt her shudder in orgasm, I felt good even though her orgasm gave me an extra large serving of Jimmy’s load. After I was done she asked me if I had a Magic Marker. I found one in a drawer, and she asked me if I would redo the lines on her belly. I shrugged and drew the lines, making a thick, black line about an inch long over each of the ink lines. I asked her why and what she said made me forget entirely that I had not cum myself. ‘Because, silly. I’m planning on fucking you a lot this week and I hope Jimmy to. When you are fucking me, I want you to remember how much deeper Jimmy fucks me so you can’t object when it’s his turn.’