Date: Thu, 14 Jan 2016 15:59:03 -0600 From: Jack Parke Subject: Rick and Bob (tt, mm, TG, TV, oral, anal) Rick and Bob/bi J Parke I've been an avid reader of the stories posted on Nifty for a number of years. This is truly a unique site and provides some great times form the wonderful stories that are uploaded to it. It also provides a venue for authors to publish their stories, which may never see the light of day anywhere else. I would urge you to consider making a donation at http://donate.nifty.org/donate.html so we can enjoy this site for a long time to cum. This story is pure fiction. It's about sex between teens, sex between adults but not with each other, and not across the age gap. It also has spanking play it in. If any of this bothers you, or it's not legal where you are, just hit the `delete' button and be gone! I love feedback so feel free to comment about the story and/or the writing style. I ignore all spam but love hearing constructive criticism from everyone! Let me know what you think... My name is Rick, I'm 15 years old and a sophomore in high school. I grew up in a normal family; mom, dad and a younger sister, Jen. Dad had a full time factory job as a supervisor and mom worked part time to help with the family's needs. But this story is about some strange things that happened to me the past few years. When I was in grade school, I was kind of a loner. I played with the boys on the playground at school; we played soccer, basketball and baseball during our lunch period and also in PE class. But after school, I kept to myself. I didn't have any real friends, just a few casual acquaintances. My athletic skill was wanting, I wasn't coordinated enough nor was I as competitive as the jocks were for the win. I was an average student, got mostly Cs and sort of "slid" through grade school. After I got out of there, I was enrolled in junior high, 6-7-8 grades. But this is where I want to "introduce" Bob into this story. Bob was the same age as me and we were classmates through grade school. Bob, or Bobby as many called him, was smaller than I was and rather thin. He had a long face and his hair was very dark, shoulder length. Thinking back now, I guess he was actually cute but at the time, I didn't see it. Bobby was smart, he was at the top of the class academically and excelled. A lot of the kids didn't like him because we reasoned he killed the "curve" when our teachers graded us. So even in grade school there were nerds! When we got into middle school, it was a confluence of 12 schools so there were a lot of new faces. My grade school class only contributed 8 boys, some had moved away and others to different schools. So in my first home room, I saw, and sat next to, Bobby. We hadn't talked much "back then" but I said "Hi" to him and he returned the greeting back. As we had 15 minutes before class, I asked "so what did you do over the summer?" "Nothing much, me and my two brothers went to the Grand Canyon on vacation" he said, "but it was a long trip driving and we're all glad to be home." "I didn't know you had two brothers, are they older or younger?" I asked. "They're both older, one is 16 and the other is 18. John is in high school and Evan is going to the local junior college here in town. So what did you do this vacation, did you go anywhere?" "Not much, I went camping and fishing with my family. Dad loves the outdoor tent stuff so we took a one week trip to the national park and got a huge tent and we camped. It was a pain, my little sister Jen is a brat and scared all the fish away!" That's about all I remember of our "first" conversation. The year got started and we shared a US History class and the teacher had us triple up and do a few projects, I made sure to include Bobby in my group as our grades were better for it. Things went on about the same over the next year also and then after 7th grade, Bobby's dad was killed in an industrial accident and they moved away. As I think back now, I remember starting to wonder about Bobby, he didn't seem to grow as much as I was growing, he kept to himself and I think I was only at his house four or five times, and only for a project. But I remember he acted sort of effeminate and our conversations stuck to the matter at hand and never into sports or whatever he was into doing; basically we never got past being just academia acquaintances. I remember I was racing into puberty and found all sorts of "new" things to do! My 3½ inch cock, which later grew to a nice 5 inch cock was cut and was the most fun thing I had ever discovered! I had a couple of school buddies and we exchanged notes on what we were doing, albeit all made up, and what we'd like to do to "her"! Or her. Or her!! And then one day towards the end of my last year in middle school, dad came home and announced he was being promoted and we were moving. We moved of all places, to London for a year. Holy cow, did that open my eyes to a plethora of things in humanity! I went to an "American school" so my education was on track with what the kids in the US were doing but we also had a lot of UK kids share the classes with us. I met up with a few of them and we used to run around together, and get the Bobbies after us too! One time we wandered into the SOHO district and did I get an education! Gays are very fluid in London and are accepted, not like in the USA. I got to see what I learned were men in drag, prostitutes, pretty well whatever I might have wanted to see. We talked to a young girl and asked why she was there, she informed me, by taking my hand and putting it down the front of her shorts, that she was a shemale and that's how she supported herself. I was springing a boner about then and she asked how much money I had, so we decided £5 was enough and I got my first blow job! It didn't take her long, after all I had seen, I was primed and ready! After she was done, she said "thanks Yank, I hang around here and maybe you'd like to try my pussy next time? Just £10!" We left and I never saw here again but it made a strong impression on me. I wasn't gay but I had just shot my load of cum into another boy; I liked girls but the shemale had made an impression on me and began to question my feelings towards the gay or "other" parts of our society. After a year had passed, my dad was transferred back to the US, only in a bigger city but still in the Midwest. I enrolled in a high school that had close to 900 kids and was like a little city amongst itself. I had the usual classes and found myself a little popular since I had spent a year in the UK. But one day as I was walking to a class, I noticed someone that I thought I knew but couldn't place. It was a cute, short girl, light colored hair you could tell was dyed but still not too hard to look at. She saw me and smiled but then looked away. I didn't think too much of it for a few days until I found we shared a social studies class. The girl's name was Bobi and during a lab one day, I went up to her and introduced myself to her. "Hi Bobi, my name is..." she cut me off saying, "Rick"; my mouth dropped open and started at her. "Do I know you? I mean, you know my name!" "Rick, my name was Bob or Bobby, back in grade and middle school. We did a few projects back then. A lot has happened to me the past couple of years; it's just nice to see someone I know. You were always nice to me when the others picked on me and I don't have any friends here at all." I was dumbfounded and just stared at her! Finally I found my mouth start to form some words and said "what happened to you?" I was almost stuttering but got out, "would you tell me?" "Yes, can you come home with me after school?" and I replied I would. I called my mom and told her I was going to meet up with an old friend from the old place and she said fine and to be home around six for dinner. After school, I got on the same bus as Bobi and rode to her stop but I stayed away from her, I didn't want anyone to know I was with "HER"! The bus dropped the two of us off and away it went. She looked me in the eye and said "I'm not going to bite! You don't have to be afraid of me!" We walked to her home, a very nice place, way above the style or luxury I lived in. We went in and she got us both a soda and we sat at the kitchen table, facing each other. She could see the questions on my face and began by explaining all that happened. She said that after her dad was killed, there was a `substantial' (later learned it was multi million) damage payment made to her mom for their safety and well being. She went on to say "you can also see I'm a girl too. Or at least I live as a girl now. When I was born, I was a boy and I have `boy equipment' but I know, in my heart, I'm a girl so that's how I live now. Mom was upset but we talked about this and she said she had some knowledge of boy/girl `confusion' and allowed me to lead this life. She used to take me shopping and she helped me pick out pretty clothes and we had a lot of fun!" She continued, "After we moved here a couple of years ago, both my brothers were in college and my mom said that she would invite `her' sister out for a visit. I was sort of shocked, I didn't know she had a sister, I had heard she had a brother." "Mom's sister, Salvatore is, or was, actually her brother at birth. I never met him as a child, mom explained that he began to dress as a woman and has lived that way for a long time and loved the entire life style as being a woman. Anyway, a couple of weeks later, `Aunt' Sally flew out for three weeks and it was the first time I ever met `her'. I always knew of her but we never met, even at any family gatherings. I guess the rest of the family wasn't as accepting as my mom was of her `sister lifestyle'. Anyway, Aunt Sally was very nice to me and we had a lot of deep discussions of what I was going through and she explained about the changes I would be going through." "So what happened, how did you become a girl? Did you just start wearing girl stuff, I can see you have boobies, and they are nice, (with a big grin) but did you just switch one Monday morning?" "No, it's not like that. Mom took me to a psychiatrist downtown that specializes in gender issues. She wrote a prescription for hormones to help start me growing breasts, which took close to a year to get to my smallish C cups I have today. I still have my penis and it works just like yours does, it gets hard and I can make it shoot off, just like you do. But I love being "Bobi" and love being a girl." I just sat there, looking at her. She had a tear run down her cheek and I leaned over and took it on my thumb, drying her face. She then asked "can I ask you to not tell anyone that I used to be `Bob'? I don't mix with the school groups, I keep to myself and my school work. Mom has a academic coach working with me and I plan on going to college but not sure what I want to major in but I don't date, I'm scared I'd get found out that I'm a `queer boy in drag' and that'd ruin me." "Mom has been talking to a lawyer about my gender, I don't have any `official government IDs' as yet but if I want to drive, I'll have to state gender when I get a driver's license." "Bobi, I'm not going to say anything to any of them. I've known you for several years, we sort of grew up together and you sure did help me with my school work stuff `cause you're so damn smart!" She gave me a huge grin and reached across the table and took my hands into her hands and I have to admit, that gave me some `stirrings' in my crotch. I took a good look at her, she was cute, maybe 5'6", 100 pound if she was soaking wet, nice tits and a very nice round ass. Just about then, her mom walked in the door and I got `THE LOOK' from her! "Mom, this is Rick, we went to grade and middle school together. Do you remember we used to get together and work on some of those assignments back then?" "Yes, how are you Rick?" I could tell she was working things out in her head and Bobi was bubbling on about having a real friend! "I'm fine Mrs. Blakely, I saw Bobi the other day and she looked like someone I knew and we finally talked today. She told me about what she has been going through and it doesn't matter to me; as long as she helps me with my school work, I'm cool with whatever she wants to do." The three of us sat around and talked for a couple of hours, I told her about living in London and she asked what all I had seen! I didn't tell her about the shemale that blew me but did mention how fascinated I was with the SOHO district and she grinned ear to ear so I was sure she knew I had done some `exploration' while I was there. It was getting close for me to go home and she offered to drive me and we all jumped in her car and she drove me home. Bobi and I decided to be friends in school and that ended my day. As time went along, Bobi and I worked together on a few projects and she helped me with my grades. As this was a huge high school, none of the coaches were looking for someone like me to play any sports so the jocks left me alone, Bobi kept to herself and I continued in my `loner' personality from when I was young. The `word' going around was that we, Bobi and I, were a couple and everyone left us alone. But I'll never forget our first kiss! We had been assigned to write a story for English and since I had lived in London, we decided to use that as the premise of our story. I went home with her one Friday afternoon after clearing it with mom. Bobi got us sodas and we sat around in her family room, trying to decide on what stories we were going to tell. We finally decided to tell my story on going to the American school and have Brit students in the class amongst us and the funny things that developed from that. We were sitting side by side at the table as I was making notes and she asked me a question about something and our faces were real close. She was looking me right in the eyes and we just sort of leaned over and tenderly kissed each other. She broke the kiss and pulled back about a foot, still not saying anything but looking me in my eyes, I took my hand and pulled her back towards me and kissed her again, only a little more aggressively. I felt her lips part and knew what was going to happen, I wasn't an expert at kissing but I had kissed a few girls in the past and knew what a French kiss was. I felt her tongue on my lip and opened my mouth, inviting it in. We kissed for several minutes with our tongues battling each other and exploring our mouths. Bobi broke the kiss and she said "I've wanted to do that for the past couple of months. I hope it didn't freak you out" and that's when I realized I had just kissed a guy! I also realized I was as hard as a rock too. "Thank you Rick, I needed that. I don't have a boyfriend and I consider you my boyfriend, if you want a girlfriend. I hope you can accept me as a girl, can you?" "Yeah Bobi, I can. I know I sure did enjoy the kiss, hell, I got hard from it!" She laughed and said "can I ask you a question?" I nodded yes and she said "have you had sex with a girl yet?" My face got as red as a firetruck! She started to giggle and her eyes told me she knew the answer. "Who was it? Did you date her? Where did you meet her?" I finally told her it was a girl in the American school and we had oral sex. I didn't tell her it was a shemale and that I had paid her for it either! The next few months, we became boy/girl friend with each other. We went to the school games, dances and school parties together; held hands like young kids do and enjoyed each other's company. Bobi's mom was happy we were together and I began to spend more and more time with Bobi. Finally one day my mom asked what was going on and I told her I had met a girl and liked her. She said if we were at a function and her parents were there, that I was to introduce her to them and I agreed. I was a little worried, I didn't know if she knew Bobi was actually Bob, or if she even remembered. I was really surprised that my brat sister, Jen really liked Bobi and pestered us to take her with us when we went out. It was in March that Mrs. Blakely had planned to make a trip for a week to visit her other sister over family matters. She called her `sis' Sally to come and stay with her but Sally suggested Bobi fly to her house and stay there. It was spring break and it would be a fun time for her to see where her `aunt' lived. Bobi and I didn't want to be apart but finally Bobi's mom decided to see if I wanted to go with her! I was up for it, so was Aunt Sally, who knew the story between us, but I had to work on my mom. Aunt Sally lived in New York and Bobi's mom talked to my mother and told her it would be a good educational experience for both of us kids and that her sister would ride herd on the both of us; mom agreed and I packed my bag and away we went! Aunt Sally picked us up at JFK and whisked us away to her condo. I had seen a few pictures of Aunt Sally, she was about 5'8", maybe 120 pounds, nice tits, fantastic ass and long dark hair. She was a very good looking woman, even to a 15 year old, she was HOT! Aunt Sally was LOADED and it showed, the condo had to cost a fortune, it was a four bedroom 2500 square foot place with a restaurant, gym, pool, room service staff for whatever you might want, basically a self contained city within the city. As soon as we got there, she had the doorman take the bags up to her apartment and took us to the restaurant as it was close to dinner time. I wasn't too hungry but Bobi ate the hell out of a NY Strip steak! As I sat there eating, I realized it was three guys that were going to be together for a week and started to feel my groin stir awake! When we got upstairs, we were shown to our bedrooms which shared a `jack and jill' bath and I understood that this might be a monumental opportunity for the two of us! We got unpacked and met Aunt Sally in the living room and had a desert of pie and ice cream plus sodas. Aunt Sally had a scotch or two and got very mellow. Then she dropped the bombshell and asked "have you two had sex yet?" My mouth dropped and Bobi grinned ear to ear! I began to stutter and all I got out was a "no" and Bobi started giggling! "Aunt Sally, you scared Rick to death! We've done a lot of kissing and he's played with my boobies and I liked it!" Then the second bombshell... "Well you've got an adjoining bathroom and I don't plan on going into either of your bedrooms while you're here. You do what you want to do! There's lube, toys, most anything you want in the bed table in each bedroom so enjoy yourselves" and with that, she said she was tired and was going to bed, and, `poof' and she was gone! I was sitting on the couch next to Bobi, overlooking Central Park and looked deep in Bobi's eyes and smiled, she leaned over and we began kissing. The view overlooking Central Park was beautiful and very romantic and as we were kissing I began to rub her tities, I could feel her nipples getting hard, as was my cock. She suddenly jumped up and pulled me by the hand and led me to her bedroom and sat me on the bed. She did a strip tease for me, slowly taking off her clothes. When she was naked, her cock was sticking straight out and this was the first time I'd seen it. It was a little smaller than mine, maybe 4 inches long and very thin. We had been chaste with each other at home, other than her rubbing me a little and me feeling her tits, nothing had occurred. But now I was presented with a hard cock! "You know, this is the first time I've seen you naked, you do have a nice cock!" "No Rick, it's not a cock. Us girls call it our `clit', it's kind of the same thing that real women have. It feels good, like a woman's clit does, and when a woman has an orgasm, she has a lot of fluids come out of her pussy and when I cum, I have cum fluids that comes out of my clit!" Bobi came up to me and started pulling my shirt off, over my head. My mouth was at the perfect level to take her nipples in my mouth so I placed my hands on her hips and drew her close to me, allowing me to suckle on her nipples and caressing her nice bottom. This caused her hard clit to touch my stomach and I could feel it was wet and sticky with precum! She then got on her knees and took my shoes and socks off, then rose up before me and started unbuckling my belt. Then she opened my waist button, lowered my zipper and had me push up so she could pull my pants and underpants off. I sat there with a hardon half way to Jersey and it was leaking precum like crazy. Next she had me stand and she turned the bed down, lay down and led me to lie beside her. We started to make out like crazy and she started stroking my cock. I told her to stop, I was going to shoot and she did. I kissed my way down her neck to her tits again and sucked on them and at the same time, stroking her clit with my hand. She held my head and directed it from side to side, all the time moaning. I think it was right then that I realized what I had to do next and kissed my way down the rest of the way and kissed down to her clit. She didn't have any pubic hair, it was as bare as a baby's butt. I kissed the end of her clit and slowly took it in my mouth and she shook like she was having a seizure. I ran my mouth up and down, paying special attention to her glans with my tongue as I fondly recalled the blow job I had in London and how good it felt! I was stroking her balls with one hand and rubbing her bottom, her legs were raised and wrapped around my back and neck. My mouth was very wet and spittle was leaking down her clit, over her balls onto her perineum region. I took a finger and got it wet and put it on her boi pussy, pushing a little and the finger went in to the first knuckle. "Oh my gawwwwdddd Ricccckkk, I'mmmm gooonnnaaaa cummmmm..." I felt her clithead swell and she jerked a couple of times and then froze and she shot a strong load of cum in my mouth! I don't know what told me to do it but I swirled her juice around in my mouth on her clit and as she shot more, swallowing what I was unable to have room for in my mouth. She finally started to shrink in my mouth and she pulled me up beside her and gave me as deep a kiss as I've ever had in my life! She broke the kiss and looked me in the eyes and said "I love you Rick, I wasn't sure for a long time but I know I love you so very much." "I love you too Bobi, we are a perfect couple and I want to be with you forever!" "Baby, lay back and let me return the favor you just gave me. I laid back and Bobi kissed her way down my body but not before paying special attention to my nipples, which I found rather sensitive and it felt good. She made her way down and slowly gave me a blow job that almost made me pass out as I shot my load in her mouth. She came up beside me, gave me a peck on the cheek and we fell asleep holding on to each other. The next morning, we made our way to the kitchen in our bathrobes and found Aunt Sally making breakfast. We sat round the table, ate scrambled eggs and sausage, toast, coffee for Aunt Sal and juice for Bobi and I. she asked if we both slept well and the both of us blushed and it told her all she needed to know! After breakfast, Aunt Sally told us she had plans for us and to get a shower, and we'd do some sightseeing. We walked back to our room(s) and realized the shower was big enough for both of us so we jumped in, showered and got dressed and ready to go. We had a fantastic day, Aunt Sally took us to see all sorts of things I've only heard of. We had a leisurely lunch and ended the afternoon with a walk in Central Park. The entire time, Aunt Sally sounded like a guided tour director, pointing out things to see and told us she had tickets for a couple of days later to a Broadway show! On the way back we stopped in the restaurant and I had a piece of cow that would normally feed a platoon of Marines! And then we went back up to her apartment. Aunt Sal told us to get in our bathrobes and we'd try something new. When we returned, Aunt Sally gave us a cup of what looked to be coffee, I've had coffee before but it was only so-so to me but this was really tasty. It was a rich blend with a shot of good bourbon in it; we sipped it and sat on the floor in a circle, talking. "I know you two finally `met up' last night and have discovered each other but I want to give you a little instruction on other things you can do. Have either of you ever fucked anyone or been fucked?" I went beet red but Bobi said "no, but Rick put his finger in me last night and it felt beyond anything I've ever felt in my life!" "Sweetheart, that's great!" then looking at me, "Rick, you need to be very careful when you fuck your girlfriend. You can do a lot of damage to her `pussy' but if you're careful, she'll love everything you do for her. I've been fucked a million times and I love taking a nice cock in my pussy, it makes me feel so much like the real woman that I am!" She stood up and went to a drawer and came back with a small velvet bag with several items inside it. She sat back down, opened the bag and pulled out a smallish, thin dildo. "This is what you should start with, you get it well lubed with the KY jelly and after you get a nice dollop of jelly in her pussy, you push this in real slow." She looked directly into Bobi's eyes and continued, "it will hurt a little when it first goes in but your man will help you by stroking your clit." I know I had a questioned look on my face and she said "Rick, Bobi's cock is her clit, women have clits and they feel real good when played with and especially when you kiss them. You push this dildo in and out, real slow and she'll relax. As long as you take the time, she'll be ready for you. How big is your cock? Here, pull your robe apart!" My face went red but she pulled my robe apart and exposed my now hard cock, "Baby, you're going to need the second dildo in you before this guy fucks you, it's large!!" She continued, picking up a second dildo, "Rick, get this one lubed up and work it in, but only after she is comfortable with this smaller one. Take your time and I swear to you, she'll be ready to take your cock and you can breed her. And sweetheart," looking into Bobi's eyes, "you take this one and while you're sucking his cock to get him ready, you put this in him and he'll love you for it, just make sure it's well coated with lube and you should get a finger lubed up and put it in first. It's the best way to make love!" She was holding up a slim, curved item with a small bulb on the end of it. She told us it would massage my prostate. Then looking at me she said "and Rick, there's no reason she shouldn't put her clit in you, it's a lot smaller than yours and I swear, you'll enjoy having her pussy juice in your bottom!" (more blushing!!) While all this was going on, we had had two more coffees and it was close to midnight. Aunt Sally told us it was time for bed but as she got up, she looked us both in the eyes and told us "feel free to play with the dildos but don't actually do any fucking. I have a plan to make that first time the most romantic time either of you will ever have in your lives! Oh, I have to take care of some business tomorrow so I'll be gone all day. Enjoy yourselves but stay here, don't try to go out on your own. I'll be home around 4 and Bobi, you and I need to do something special, just between us girls! Then tomorrow night we are going to an off-Broadway play with my special friend Bill... goodnight!" Bobi and I walked to her bedroom and I was asleep on my feet. The three shots of bourbon had hit me like a ton of bricks. I lay down beside her, we kissed each other and both fell sound asleep. The next morning, we got up, walked to the kitchen and found a note for us to call room service and order our breakfast, and we did. It was delivered rather quickly so we sat and ate and chatted about what we were going to do all day. "Bobi, I love you and think I really want to have `real' sex with you. Why don't we take a shower and get out the toys your aunt said are there and experiment?" "Sounds great Rick, I'm excited to have you `pop my cherry' and hope it's soon! I've talked to some of the girls at school and they've asked me if we've fucked yet and I told them no, but hoped it would be soon. Most all of them have been `bred' by their boyfriends and I want to be like them!" We went upstairs, showered and flew into the bed! Bobi found the dildos, lube, a long slender curved one with a small bulb on it (for me) and we spent the afternoon experimenting with how they worked. When I put the small dildo in Bobi the first time, she said it hurt and to pull it out! I jerked it out real quick and she said to put some lube on my finger and put it in real slow. I did and she seemed to relax and it went in without giving her any pain. Then when I put in the dildo, I had a lot of lube on it, and pushed it in real slow. As the dildo head popped through her sphincter, she said to stop and let her get used to it, and I did. When she said she was ready, she told me to push it in real slow, and I did. It didn't take long and she wanted the slightly bigger one so I repeated what I had done with the small dildo and it didn't take long and she said she was going to cum. I immediately lowered my mouth on her clit and she shot a load of gurl jism in my mouth. Then she got the slim one and did the same to me, when she hit my prostate, I shot a load of cum in her mouth, I damn nigh drowned her! We finally quit playing around 3 and watched some TV for a while and then as expected, the door opened around 4 and in walked Aunt Sally with a man I had not seen before. She introduced him as her `friend' Bill and said he was taking us to the Broadway show tonight. Bill was a good looking guy, smartly dressed in a suit. He stood close to 6 foot, maybe 200-210 pounds and what looked to be good shape. He had dark hair and the start of a 5 o'clock shadow that looked good on him. Let me put it to you this way, I wouldn't have messed with him, he looked like he could handle himself and I would rather have him on my side! We sat around for a few minutes and chatted, Bill told us he was a stock broker on Wall Street and enjoyed the theatre and found a show he felt teenagers would enjoy. Suddenly, Aunt Sally jumped up and said "Bobi, come with me!" took her hand and poof, they were gone. Bill and I talked about sports, the football Giants v Jets, and I was able to talk with him, he was about as much a sports fan as I was, not much but enough to talk to a client about the subject. Aunt Sally and Bobi were gone for close to an hour and then Bobi came back in a robe and told me come with her, she said Aunt Sally wanted us to get ready to go out as we would be having an early dinner. I joined her and asked "What were you and Aunt Sally doing?" "It's a woman's secret but I got to see her bed, it's huge! It's bigger than king size, it's round and her bedroom is beautiful. We took our showers, got dressed and joined Bill and Aunt Sally in her living room. Bill had a car waiting for us, we went to a steak house and had a great meal and after that to the Broadway show. It was a fun show, all about the bleachers in Wrigley Field and I really enjoyed it. After that, we headed back to the condo and got there around 9:30 and went up to the apartment. Aunt Sally poured everyone a drink and we sat around and talked about the show. Then she changed the course of the conversation saying "Bobi, as I told you earlier, we are going to make this the most memorable experience of your sex life you'll ever have! Bill and I are going to introduce you both to some new things and hope you enjoy what you see and what happens." Saying that, she stood and took Bill by the hand and indicated for us to follow, and we did, to her palatial bedroom. A side note here, I had noticed one thing, the entire evening, Aunt Sally had behaved like my little sis Jen did, she was a consummate, but fun, brat. She poked fun at Bill and us also, nothing really cutting but just little short verbal jabs about anything and everything. I found it funny, she was putting on quite she `floor show' and we had a fun time. As we entered the bedroom, Bill asked us to sit on the edge of the bed and said he had some `business' to take care of. "Sally, get that chair from your dressing table and put it right here!", indicating where he was standing. "Now, get that hairbrush off your dressing table and bring it to me!" "Oh no Bill, are you going to spank me? In front of the kids? Oh please Bill don't do that, it will hurt!" "Sally, you have been a brat all evening and you are going to pay for what you have done. These kids need to learn there are consequences for their actions and they are going to see how it's handled; maybe if Bobi gets snippy, Rick might need to handle things for himself too!" I was too excited to blush, my cock was straining in my pants. Bill had Aunt Sally stand before him and he pulled her pants down to the floor, followed by her lace panties and we could see her bottom. Then he told her to remove her blouse, "spankings are given to naked, recalcitrant, naughty people!" "Oh please Bill, please don't make me get naked in front of the kids, it'll be too embarrassing!" "Nonsense Baby, you don't have anything the both of them haven't seen by now!" And with that, off came the rest of Aunt Sally's clothes. Then he turned her sideways to us and slowly pulled her over his lap. I noticed that Aunt Sally's clit was sticking straight out so she was excited. Bill began to spank her, it was apparent to me from the few spankings I'd received as a kid, this wasn't really a punishment spanking. When his hand would fall on her bum, she would let out a small `whimper' but nothing much else. He spanked her for a while and then stopped and stroked her bottom which allowed her time to recover. Then he leaned over and grabbed the hairbrush and I knew the real spanking was about to start! Aunt Sally's bottom was pink as Bill raised the hairbrush and as it struck "SMAACKK", Aunt Sally yelped "AAIIIIEEEE, That hurt! Please don't do that again" only to be followed by "CRRAAACKKK". "YYEEOOOWWWWW, PLEASE NO MORE, THAT HURRRTTTTTTT..." Bill responded "Baby, you know a spanking has to hurt to be good and this is going to be good so hang on, you're going to pay for being a brat all night!" Bill spanked her for close to 15 minutes; he would spank her with the hairbrush then stop for a minute and stroke her bottom, then start all over again. Aunt Sally was crying real tears, we could see them go down her cheeks and fall from her nose to the floor. While all this was going on, I was holding Bobi as close as I could and began to stroke her crotch as I could feel her clit growing. I was as hard as I had ever been in my life and we began deep French kissing while we heard Aunt Sally take her spanking. My hand was inside her slipover shirt and she simply took it off and unfastened her bra. She also pulled my shirt up and off and we both unfastened our pants. By the time the spanking was over, we were both almost totally naked and Bill was the only one with clothes on. Bill helped her up off his lap and had her kneel in front of the chair where he sat. She knew exactly what was expected of her, Aunt Sally unfastened his pants, allowing his hard cock to stand out. Aunt Sally began to suck on Bill's cock and it was apparent he was really enjoying what she was doing. Bobi and I were no longer watching but what we were hearing was so exciting I felt we would both cum soon. Bill stood up and when he did, his cock fell from Aunt Sally's mouth. He told her "get the special cushion, I'm going to breed you tonight. You've been a total brat and this will be part of your punishment!" "In front of the kids?" Bill smacked her ass and it was a hard swat, I could see the outline of his hand on her ass cheek. Aunt Sally got a cushion, about two feet wide and four feet long and it was apparent if she lay over the top of it, it would put her bottom in a raised position. Bill stepped forward and had her lie on it, there were Velcro strips to secure her legs apart and her arms at her side. "Rick, when a woman has been naughty, like Sally, sometimes it's necessary to `put them in their place' and that's what I'm going to do. I'd suggest you watch and maybe we can do a bit more when I'm done." By this time, both Bobi and I were totally naked and my cock was oozing precum, as was her clit. Bill got behind Aunt Sally, took a dollop of KY jelly and put it in and around her pussy. Then he lined up and with a quick push, ran his cock in her pussy. The only thing we hard was the sound of skin on skin and Aunt Sally moaning. By this time, I had my lubed finger in Bobi and knew this would be the night we would both lost our virginity. Bill was driving in and out of Aunt Sally and it wasn't long and he suddenly drove in as deep as he could and held his place. I could see his balls were drawn up and his ass cheeks were quivering. I could also hear Aunt Sally moaning and whimpering for him to `fuck her' and I saw her clit start pumping its white juice down the side of the cushion. Finally, he plunged forward and let out an "AAAIIIIIIIIII I'M CUMMMMMIIINNNNGGGGGGG" and I could see him shaking as he drove his jism into Aunt Sally's pussy! When Bill was done, he slowly withdrew and asked me to let Sally up, meaning to release her bondage strips holding her in place for her breeding. As I did, I could see the white cum leaking from her and I put my finger on it and ran it up and down. Aunt Sally jumped a little and then said "Oh my gawd, rub that for me!" As I did that, Bill dropped on his back on the bed, face up with a huge smile on his face. Aunt Sally pushed herself up, grabbed a towel and sat next to Bobi on the bed and hugged her. Bobi had tears in her eyes and asked "did that hurt? It looked like you both enjoyed it when he was fucking you. Did the spanking hurt? Oh Aunt Sally, I'm scared!!" "Quiet child, it was wonderful and I loved all of it, especially the spanking! Bill gave me an erotic spanking and you need to learn there is a fine line between pain and pleasure and that spanking was pure pleasure!" They continued to hug and then Aunt Sally put her lips on Bobi's and they enjoyed a deep kiss which made me get harder than I already was! She continued, "Bill is a gentle lover and so very kind to me. Please relax and let things happen, you remember what we talked about this afternoon?" Bobi gave an affirmative nod... "Let this go the way it needs to go and I promise you'll enjoy what is going to happen next!!" Bobi was sniffing her nose and I gave her some tissues and she blew her nose. Aunt Sally told me to come sit next to Bobi and give her a lover's kiss, which I did. I noticed Bill was up on an elbow, watching and taking in everything that was happening. I didn't know what was going to occur but I was sure hoping I was going to get to fuck Bobi! Both Bobi and I were hard, we had been kissing, fondling and I had kept my finger in Bobi's pussy for the past half hour. I could feel her `pussy muscles' holding my finger in place and I was ready to do more! "Bill, lay down..." Bill laid flat on the bed with his legs together... "Bobi, lay on top of Bill, facing him..." "I don't understand Aunt Sally, what do you want me to do?" I could see the fear in Bobi's eyes, I think she knew what was about to happen and she was terrified it was going to hurt. I know from some of our conversations that she said she had heard from her friends how much getting fucked would hurt. I leaned over and gave her a tender kiss and when we broke, I held her face in my hand and told her that I loved her and would never hurt her. She smiled back at me and said "I know you won't hurt me Rick, but please be gentle!" "Baby, Bill is going to cuddle you for what's about to happen. Rick is going to take your virginity but it will be easier if he enters you from the rear. So lie on Bill and allow him to help you with this." Bobi laid down on Bill, he gently held her to him and was whispering in her ear little things like `it's doing to be OK baby', `let this happen, you'll love it'... Once Aunt Sally had Bobi on top of Bill, she placed Bobi's legs on either side of Bill's legs; "Bill, spread your legs apart" and that caused Bobi's legs to be flayed very wide! Then she took my arm and led me to kneel between Bobi's wide spread legs. I knew I was about to lose my virginity and I was leaking precum like it was running out of a full open faucet! Aunt Sally produced a handful of KY and slowly stroked my 5 inch cock, placing it at the entrance to Bobi's boi pussy. I was ready to just `stab' it into her, but Aunt Sally held me back. She was whispering in my ear what to do... "Baby, rub your cockhead on her rosebud, take your time... Bobi, remember what I told you today, push like you're trying to take a bowel movement..." I noticed Bobi move a little and her pussy lips `winked' at me, I was so ready to enter her! My cockhead was at her pussy lips and they `winked', I pushed forward slightly and my head popped inside her! Bobi let out a `yelp', I had hurt her and I didn't want to do that! But she went quiet as Bill slowly stroked her back, whispering comforting platitudes in her ear. I stayed there with just my cockhead beyond her sphincter, allowing her to get used to its intrusion. Then she lifted her head from Bill's chest, turned and looking at me said "go ahead Rick, push it in but go slow." Aunt Sally still had my cock in her hand but she removed it and laid her hand flat against my abdomen, she put her other hand on my ass and very slowly allowed me to enter Bobi. It took four or five minutes for my cock to go in but I felt my balls resting against her as I bottomed out. Bobi had been gasping slightly, I knew to take my time and when I was all the way in, I said "Bobi, does it hurt?" "No baby, but just hold it there until I get used to you being inside me!" "I will sugar and I love you so very much!" "I love you too and thank you for taking my virginity and my cherry!!!" As she said that, I slowly began to pull back, being careful to not pull all the way out. When I was at the end, I waited for a minute and then slowly began the trip back to the bottom of her pussy. Once there, I waited a minute and then began the trek back to the start. The feelings I was getting from her pussy walls were indescribable, I could feel her tighten her pussy (I later learned she had been practicing `Kegel' exercises) and then relax it. I'm not sure how many times I went in and out slowly but I felt a `lump' in her pussy and recognized when my cockhead went past it, Bobi gasped but I could tell the gasp was a pleasure gasp! After five or six trips, she let out a gasp and then said, in a demanding tone, "FUCK ME RICK!!! FILL MY PUSSY WITH YOUR COCK!!! GIVE IT TO ME!!!" That's all it took and I began to fuck her in earnest. Every time I pushed forward, the feelings were growing so fast that I felt I was going to cum! Bobi was writhing on top of Bill, he was holding on to her for dear life! As I would lurch forward, I would let out a "UGGGHHHHHH", stop and repeat it again. I knew I was close but suddenly I heard Bobi... "OH SHIT, I'M GOING TO CUUUMMMMM... FUCCKKK MEEE RICCKKK... PPUUMMMPPP YOOUURRR SEEEEEDD IN MEEEEEE... OOHH MMYYY GGAAWWDDDD... II'MMM CCUUMMMMMIIINNNGGGG..." and Bobi shot her cum all over Bill's chest! And that's when I felt Aunt Sally insert the curved toy, it hit my prostate... I could feel Bobi's pussy walls massaging my cock and that's when I lost it... my cock felt like it grew two inches and then suddenly, "IIII'MMMM CCCCCUUMMMMMMIINNGGGGG" and I flooded her pussy with my cum. I wasn't counting but I think I deposed a gallon of my love juice inside her, I had never in my life felt anything as good as what had just happened!! I lay on her back, gently stroking her hips as my cock began to shrink. It fell out and I fell on my side, still holding her hips. Bobi lifted herself up from Bill's chest and lay, facing me, with Bill on her back side. Aunt Sally lay facing me so the four of us were lying on the bed, slowly fondling each other after this great event. I looked Bobi and told her "I love you baby, I want to be with you forever!" "Rick, we're young but I know I love you, you have been so good to me for the past few years and I love you for that. Please don't ever leave me!" I woke up the next morning after a totally sated rest, and saw my baby lying beside me on her back, softly breathing. I leaned over and kissed her softly on her lips and hey eyes opened and she smiled. I lifted myself up on my elbow and said "good morning love. How did you sleep?" "I slept better than I ever have. I love you so much, Rick. I want you to fuck me every chance you get!" I chuckled and pointed to the wide cushion Bill had used to fuck Aunt Sally, the two of them were up already and one of them had set the `magic cushion' on the bed, I wondered if it was a suggestion? "Want to give it a try?" "Are you going to spank me too? Please spank me, I want to see what Aunt Sally felt last night. But please don't spank me hard!" with that, Bobi got up on the cushion and lay down. "Please fasten the Velcro strips to hold me in place, I really want to feel what it feels like to get spanked. Well who was I to refuse that hot request? I got up, grabbed the `dreaded' hairbrush. I walked over next to where the cushion was and put her legs and arms in place. Then I began to pat her bottom, very lightly. But she lifted her head and told me to "get busy, do it right!" And again, who was I to refuse such a hot request. I began to land the hand smacks harder and harder on her bottom, I could see her bum getting pink and I knew she was feeling it. "Owww baby, that hurts. Please don't hit me so hard. Plllleassseee Baby, that hurrrssttttt." I ignored it and remembered what Bill had said to Aunt Sally so I responded with "Baby, a spanking has to hurt to be good and I'm going to make this a good one!" I spanked Bobi for quite a while, after my hand started to hurt, I picked up the hairbrush and Bobi really started crying and pleading with me to stop. She was getting louder and louder and I wondered if the entire building heard her! But finally I stopped and walked over to Aunt Sally's makeup table and grabbed a tube of Aloe Vera lotion and began to apply the cooling lotion to Bobi's red bottom. "Oh Rick that feels so good! Oh Rick, put some in my pussy. It needs to feel you again... Please hurry!!!" I put a dollop on my finger and plunged it into Bobi's pussy, then I coated my cock and lined up my cock with her pussy. As soon as my cockhead touched her pussy lips, I saw them `wink' at me and pushed forward. I entered her easily and waited but after just a few seconds, Bobi told me to plunge in. "Fuck me Rick... I want to feel you pump your seed in me!!!" I fucked her for less than two minutes and I lost control and pumped another huge load inside her! I couldn't believe how lucky I was, I had a loving girlfriend and a partner. As I withdrew, I released Bobi from the cushion and we heard applause from the bedroom door jamb where Bill and Aunt Sally were standing. They were in bathrobes and smiling like Cheshire cats! "Well, well, well, I see you two are up! And I see you found the cushion we left for you to try, we loved watching all you kids did!! But I see one thing we still need to do" Aunt Sally said as she walked towards the bed. I was kneeling on the bed and Bobi had gotten up and was standing next to me displaying a hard on (she hadn't cum during our tryst!). As Aunt Sally got there, she took my arm and forcefully `directed' me to lie on the cushion and very quickly fastened the Velcro strips, holding me in place! "Bobi, Rick," she paused, "Bill and I enjoy a very satisfying relationship but it is built on trust. And from time to time, both of us `mess up' and have to pay the piper for our actions. Rick, you just spanked Bobi for nothing she has done and that, young man, is inexcusable. So Bobi," handing her a leather paddle, "here's an implement you need to use on Rick's naughty behind! You need to turn his bum nice and red and then fair play says you need to breed him yourself!" I could feel my face getting beet red, I was as embarrassed as I had ever been in my life. But things were happening fast and all of a sudden a loud "CRACK" and I grimaced, I didn't make a sound, I was tougher than she was!!! I felt a strip of `fire' across my ass cheeks, it burned and hurt like hell! "CRACCK" again and I kept my teeth tightly locked, not emitting a sound. "PPOOOPP" and I yelped! "Damn it, that hurt!" I said. Bill sat down at my head and was massaging my neck, I heard him whisper "Son, you need this, it hurts but what follows is going to be the most absolute gift you'll ever receive when she's done working your ass over!" But damn it, it really hurt. My ass was on fire and I began to openly sob. But the spanking didn't end, Bobi kept on delivering those horrible swats on my bottom and then she moved to the back of my thighs! Holy shit, that REALLY hurt! And my legs were parted and she addressed the space between them and that was worse yet. It was finally over but I was still bawling my eyes out. I had NEVER been spanked like that in my life. My parents had spanked me a time or two growing up but it was two or three swats and then it was over. It hurt but nothing like this. Suddenly I felt something cool and recognized someone was applying a lotion to my obviously bruised, most probably bloody, bottom. (I checked later, not a bruise or cut!) I opened my eyes and Bill was gone, I couldn't see behind me but the application of lotion continued. Then I felt the application to go my balls and cock, it was a smaller hand so I knew it was Bobi applying the crème and she really knew how to make me feel good. Not a word was said and I felt her middle finger sink into my ass, I knew I was going to feel her 4 inch cock in my ass and I was going to lose my virginity to her. Fortunately for me, Bobi's cock was smaller than mine. The hormones she had taken had stopped her clit from growing past its 4 inch, ¾ inch thick size. She had a cut clit and I loved sucking it, it fit easily in my mouth. Still with nothing being said, I felt the head of her clit at my rosebud and she easily inserted it in. The pain level was minimal; it actually felt good when she pushed it forward. "Oh baby, that feels so good!!! Ram it in me, keep going, oh yeah, fuck me harder!" She did, she got into her rhythm and began to lunge forward after each retreat. And every time she went in, she massaged my prostate and I was loving that! I had just cum less than a half hour earlier when I fucked Bobi when she was on the cushion so I was just `along for the ride' until I heard her say "II'MMM CCUUUUMMMMMIIIINNNNGGGGGG!!!!" I felt her clit swell and then felt the warm flow of fluid in my bowel. She gave a few more lunges and deposited more and more of her juice, it was great. And then all of a sudden, I shot a load down the cushion, there had to be another gallon of my jism dribbling down that cushion! It felt so damn good. Suddenly, it was all over. Bobi pulled out, released me from my bindings and we laid side by side, kissed each other tenderly and fell asleep. We didn't sleep long and woke up, put on a couple of bathrobes we found and headed for the living room. We found Bill and Aunt Sally sitting there, both totally nude! Aunt Sally got up and put on an apron and led us to the kitchen and fixed us some breakfast. The clock showed us it was 1pm already, the entire morning had been used up! We spent the rest of the day playing with Bill and Sally (she had insisted we call her `Sally' and drop the `aunt'), we really had a fun time. Bobi told me that Sally had given her a douche the previous day, she said that the douche would clean out the pussy for a gurl's lover and she said it wouldn't hurt me to have one once in a while if we were going to swap fucks! A few days later, we got off the plane at Ohare and found Mrs. Bartlet and my parents standing by the luggage claim, all smiling like crazy. We all hugged, gathered our bags and headed for our respective cars. As we were going out, my dad had his hand on the back of my neck and chuckled and with a `knowing voice' said, "you dog you!" This all happened a long time ago. We both graduated from high school, Bobi at the top of our class and me making the upper 50% of the graduation class possible. Bobi went on to college, got her degree and then on to law school and took a prestigious job with a top Chicago law firm. Me? I went to trade school and became an electrician, rising to General Foreman on construction projects. During our vacation in New York, Bobi's mom's attorney found a genial Cook County judge who signed an order changing Bobi's legal gender from male to female which solved a lot of Bobi's concerns. We dated for many years and after Bobi got the job with the law firm, we married and are living the good life... the sex, spanking and loving is all great... and frequent!