Special Time of Life

by Tiffany Roberts

 

This is my story and it all begins many years ago at about the age of 6. First maybe I should tell you a little about myself.

My new name is Tiffany but originally it was Stephen. I was born in the upper Midwest of the US in a rather large metro area but our house was in the suburbs. My family was extremely normal and healthy but we had our little quirks. I was the youngest child of two with happily married parents. Being in a middle class family in an extremely normal family in an extremely normal neighborhood made it difficult for everyone to accept me for who I was but they all handled it better than I guess should have been expected.

Everything started to change in my life when I was about 6 years of age. This is when I started wearing my sister's cloths and having a blast doing it. My sister had this wonderful pair of patent leather red boots that were rather tall, coming up almost to my knees, with a 2-inch heel on them and I just fell in love with them as a child. I would routinely agree to do the dishes with my sister or whatever chores needed doing as long as she would let me wear her boots around her room and play games with me. I loved the feel of sliding my bare foot down into the tall boot, the soft feel of the nylon on the inside and sliding the zipper up to encase my legs. At this young of an age I felt so comfortable wearing them that I just didn't see anything wrong with it. To this day I have a boot and high heel fetish that seems like it can't be controlled. Almost every night for at least a year I would go into my sister's room in the evening, slip on her boots and play with the toys in her room. Luckily for me she loved the company and wanted someone to play with so it was never a problem. It was also never a problem with my parents because they never came in her room to see what I was wearing or what we were doing. As long as we weren't arguing, they weren't going to bother us. My sister's room was the only room on the second floor so it would have been out of their way to come visit us and with the way my dad crashed on the couch every night – surprise visits were rare at best even on the first floor.

After about a year I grew out of my sisters red boots but I grew into some of her other clothes. One weekend our parents were out of the house for an evening with friends and my sister was in charge of me (my brother must have been out of town) and I remember her dressing me up in her dresses and school uniforms. Even though she was several years older than I was - I was still able to wear her clothes even if they were a little big on me. She played dress up with me all evening and we played Barbie's on her bedroom floor between outfits. I loved playing with my sister and never saw a problem with it at all. Some of you may hope something sexual happened between she and I but nothing ever happened. Sorry but she just enjoyed having someone to play with in the evening and I enjoyed it also. She would dress me in my favorite dress of hers, a long pink floral cotton sundress that felt very tight against my waist and was heavenly to walk around the room in. She dressed me in one of her short skirts that she wore to a party and had me wear a pair of tights that made my legs feel very nice. I thoroughly enjoyed it when she dressed me in her dresses and skirts. I also enjoyed putting on her school uniform (Catholic School!) because it made me feel so much older. We had a blast together and laughed constantly.

When I turned 11 (my sister would have been 15) my sister decided she was to old for me to play with so I was kicked out of her social life pretty much and was forced to start playing alone. It just seemed normal for me to continue dressing up in her clothes and continued to play with her Barbie's but now I was doing it secretly in my own room and loved every minute of it. When I would be out with my friends I never mentioned any of this to them because I somehow knew they would never understand but I still loved doing it. I would rush home from school and if I didn't have baseball practice or my friends didn't want to play outside, I would just slip into my room and get dressed up. It was usually the same outfits over and over but occasionally I'd find clothes my sister was done with and I would steal them for my collection. I'd hide them in a trunk I had in my closet that had a wonderful lock on it that nobody else had a key for. I was safe with hiding my sister's clothes in there and nobody would ever find out.

The clothes I always went for were underwear, dresses, skirts, boots, heels of any type and swimsuits. I loved wearing my sister's stuff because she had wonderful taste but occasionally I'd steal something from a friend's house and they would never know. My friend John had a beautiful mom who was Vietnamese and she had wonderful taste in clothing. I would play in their basement occasionally with John and I would notice when his mom had clothes for the Salvation Army and I would usually steal something from the pile when I had a chance. I don't know why I enjoyed it so much but it was so much fun to dress up. On occasion I would perform a little theft at a local store and was extremely lucky to never be caught. I would never recommend this for anyone else but at times you are desperate for new panties or nylons and you can't find those just anywhere when you are a 12-year-old boy.

In the evenings when I dressed I would first put on a pair of panties and feel the soft satin material as it slid up my legs. Second would be a pair of panty hose. I was never able to find just a pair of stockings so I was stuck with panty hose. I'd carefully slide them up my legs, making sure not to snag them and slip them over the panties. I loved the way the nylons made my legs feel, soft, shinny and smooth. Usually the next step was a dress my sister had purchased for a dance she attended in the 8^th grade. It was a blue cotton dress that buttoned up the front and had fringe around the bottom. It came to just above my knees and felt wonderful over the nylons. I loved the feel of my ass as it slid under the dress because the nylons were so slick. It all felt very sexy. Last were my shoes and I had a pair of tall black boots I had found outside a thrift store. They were tall enough to come almost to my knees and were made of very soft leather. They must have been very expensive for someone but I never saw them in a catalog so I never knew exactly. I would push and work my foot into the boot until I was settled into the bottom and could feel the leather encase my legs and feet in a very comforting way. The 3 inch heals were a joy to walk on and I loved the way they made my body swivel when I walked around my room. I felt like a girl, acted like a girl and looked like a girl and it was wonderful.

When I turned 13 I guess I started to make the transition from dressing up to being sexually excited and often would masturbate while dressed in my feminine clothes. I loved dressing up, sliding into a long flowing dress and dancing to the music on my turntable while I played with my body. I'd sprawl out on the floor and masturbate while I felt my body in the clothes. I don't know why the connection was made but it was definitely made at about this age. At this point in my life I was probably dressing 5 times per week but would masturbate at least once per day and sometimes two or three times.

During this time I always found myself staring at the girls in class and could never take my eyes off a girl named Judy. I always thought of this as a sign that I had a crush on her but in reality it was her hair and clothes that I had a crush on. I always wanted to get my hands on her outfits and I loved the way she looked in them (I didn't go to Catholic School like my sister because money started getting tight). When the boys looked at her I became jealous because I wanted the attention. While I never made the connection that I was gay, many of my classmates would refer to me as the gay kid or make comments that I was a fag. I was always the smallest kid in my class and my long blonde hair, parted in the middle and feathered back made the guys joke that I was trying to look like Farrah Faucet. They would tease me about my hair but I loved the way it looked and it felt natural for me. I'd argue that I wasn't gay and that I liked the different girls but in reality I didn't have sexual feelings about anyone in particular. I was more sexually interested in my new clothes than in any person in particular.

When I turned 14 and was a freshman in high school, I still wore girl's clothes in private but it was getting really hard to find new outfits. I was still very small, only about 5'3 (I'm only 5'6 now) and was very thin at probably 85 pounds but I was having difficulty finding clothes that either fit me or that were in style. My sister had gotten pretty fat so her clothes no longer fit me plus her clothes were horribly ugly. My friend's mom who I would steal stuff from on occasion was buying some really ugly polyester clothes for some reason so all my sources dried up. I would still wear panties on a routine basis but finding dresses that were in style was getting really difficult to come by. I would routinely shop through the Spiegel's, Sears (they still had one back then!) and JC Penny catalogs for clothes I wished I could have but they were always out of reach. I would enjoy looking at each page and picking out one outfit on each page I wished I could have. Imagine the wardrobe you could have if this fantasy ever came true!

It should also be noted that while I was 14 I also decided it was time to rid my body of all hair. I don't know why I started doing it but for some reason I got the idea that body hair was a horrible thing for me so every week I would shave my entire body while I took a shower. I enjoyed the feeling of my skin much better after it was done but I never understood why I was doing it either. My sister and mom always had stuff laying in the shower so I guess it just became a normal thing for me. Nobody ever noticed that it was done because I didn't have much body hair to begin with and since none ever came in, they didn't have much to compare it to. My friends would tease me occasionally that I looked girly or like a kid but it really didn't bother me as much as I enjoyed the effects of my shaving. I can only guess today why I started. Maybe it was the hair poking out under my panties or through my nylons. Maybe it was the feel of my naked balls and penis. Don't know. I never stopped though – that's for sure.

During the summer I turned 15, my life completely changed from anything I knew and changed everything about me. I developed a friend named Spencer who lived a few blocks from my house and Spencer was a wonderful boy. He was new to my neighborhood (having moved from Denver to our city) and we met while shooting baskets at a court near our houses and from the first day we knew we would be great friends. Spencer was almost 17 and was quit a bit larger than me with a strong upper body plus he was very outgoing versus my quiet demeanor. Right away Spencer started talking up a storm and before I knew it we had plans to do something that evening. He decided we needed to go to the mall and play some video games and that it would be his treat since he didn't have anyone else to do things with and I was completely out of cash.

Spencer borrowed his parent's car and picked me up about 6:30 and we were on our way. It wasn't an overly exciting evening but it was right then that I noticed how beautiful of a person Spencer really was. He joked about everything and played very physically when we joked around and it seemed like everything he did was special in some way, somehow different than I had ever experienced. Spencer wore nylon soccer shorts and a T-shirt with sandals and I noticed how perfect his butt and legs were when he walked across the food court at the mall. Seeing the perfect roundness of his ass and the muscles in his legs was very exciting for me and something I had never before felt before then. I had never felt this way about anyone in my life but right then and there I felt like I was in love with him. It blew me away that I was feeling this way about a guy but it also felt so perfect at the same time. We joked around, shopped at a few different stores like the record store and the gag gift store and played tons of video games. When we went home it felt so right sitting in the car with him but I never said anything or did anything to express my feelings. I just knew he didn't feel the same way so it didn't matter.

After that evening whenever I dressed up I would always take extra care to look wonderful and would pretend my pillow was Spencer. I would imagine what it would be like feeling his body and what it would be like for him to kiss me and I could only imagine how wonderful it would feel. I decided I needed to lose a few pounds (not that I really needed to) to look better but I also was sure Spencer would never feel the same way about me. I was a mess thinking about him and knowing nothing was going to happen and yet I wanted it so bad.

A few weeks later Spencer asked me over to his house for the evening because his parents were going out of town for the night. I was supposed to sleep over so that his parents didn't make him go to his aunt's house for the night. I never understood why I had to be there for him to stay at home but I guess his parents trusted that I wasn't going to be doing anything wrong. I packed up my sleeping bag and packed a bag with my toothbrush and stuff and walked over to his house (only about 3 blocks away). For some reason I had left on a pair of baby blue satin panties I had stolen from a store and I must have done it either subconsciously or just completely by accident but either way there I was wearing them. I figured it wouldn't be a problem since I'd just be wearing my jean shorts all night. Even when I slept I figured I wouldn't be taking off any clothes so I just left them on and didn't turn around to change.

When I got to his house his parents were already gone and pizza was ordered and supposed to be delivered soon. He had rented a few movies for the evening and he was planning on playing some Atari games most of the evening. I had never played an Atari except at a department store so I was very excited about playing some games.

It wasn't long and Spencer and I were in a heated battle of tank wars when the pizza arrived so we decided to eat and watch a movie. He had rented Poltergeist and Tootsie and asked me which I wanted to see. Amazing. Here I was wearing women's underwear and he is wondering if I want to watch Tootsie. I decided to sound a little tough and said Poltergeist knowing it would probably scare me to death seeing that. Luckily it was still light outside but in his family room it was rather dark because of a porch covering all the windows plus drapes. I guess his parents enjoyed it being dark in there because that was the result. Spencer lay on the couch and I sat on the floor and we ate pizza, drank soda and watched the movie. I kept jumping for my life every time something scary occurred and Spencer routinely laughed at me and joked that I was a wimp. Sure I was a wimp but that was one scary movie. Whenever I hear the line "they're here" I still get a little creeped out.

After the movie we played a bunch of Atari games and I got pretty good at some of them but never was able to beat him. He must have played that thing constantly because no matter what I did he had a way of beating me at those games. It really wasn't fair but I loved playing them and I enjoyed sitting next to him on the floor.

After a while we got tired and decided we'd watch the second movie. Even though I loved dressing up in women's clothes I really didn't have much of an interest in watching this movie and Spencer joked about it a little but was very quick to point out it was his parents pick to watch on Sunday night when they returned. We watched for a while and got sort of bored so I figured now was a good time to go pee. I'd been drinking soda all evening and really had to go so I got up, excused myself and went to the bathroom down the hall. As was my usual routine I sat down on the toilet like a girl to pee and when I finished and stood up in walked Spencer. Here I am, completely naked from the waste down with a bald penis and balls, girl's baby blue underwear around my ankles (with my jean shorts) and this guy looking at me. I was horrified. Spencer looked at me, giggled and started telling me I had just missed a really funny part of the movie. I grabbed my shorts and underwear and pulled them up quickly, turning away from him hoping he wouldn't notice the shiny material or my bald penis. To my surprise Spencer ignored everything and went on to tell me about the scene I had just missed. I laughed at his story but wondered if he had noticed anything was different about me. I washed my hands and got out of the bathroom quickly hoping nothing would be different.

Spencer and I went out to the family room and continued watching the movie but the entire time I was really self-conscience about what had happened and what he had seen. Why did I wear the damn underwear and why didn't I just lock the bathroom door like everyone else in the world? I lay on the floor and Spencer lay on the floor also but at the other end of the couch and we watched for a while before he stopped the movie. Damn, here it comes.

"This movie sucks, wanna play some more games?" He asked.

"Sure" was all I could get out of my mouth. Could I be this lucky? Had he just completely missed my complete screw up? Was I not going to get my butt kicked?

We started playing Space Invaders and we sat right next to each other on the floor taking turns at shooting the aliens. When it was his turn it always seemed to take forever until he died but when it was my turn it seemed to take just a few minutes. After a few turns it was mine again and I was really doing well when Spencer leaned over and kissed me on the cheek. I ignored it for a second wondering what had just happened and then I turned to look at him during a break in the action and he gave me a quick kiss on the lips. Damn. What had just happened? After the kiss he pulled away, smiled and said, "I like your outfit."

"Thanks" was all I could respond and promptly turned two different shades of red while I continued playing. With my mind all screwed up wondering what this meant it didn't take long before my turn was over with. Spencer picked up his joystick and started playing and I watched him wondering what he was thinking. I looked at him in his tight jeans and loose Adidas T-shirt and worried about what he was thinking about. It didn't take long and he dropped his joystick, turned to me and kissed me on the lips again. This time he turned his head and started to slide his tongue into my mouth.

Was this really happening?

I gladly accepted his tongue into my mouth and sucked on it as he explored my mouth and played with my tongue. He moved closer and ran his hand up my leg and it didn't take long for me to have the hardest prick I'd ever experienced. I thought my shorts were going to burst I was so hard and butterflies were buzzing my stomach like I had never experienced before. I kissed him back as best I could and before long we were lying next to each other on the floor.

Spencer ran his hands the length of my body, rubbing me and gently putting weight on me while he climbed on top of me. I could feel that his cock was also really hard when it rubbed against my bare leg through his jeans. After a few minutes he pulled himself off of me and rolled onto his back right next to me. I lay right next to him, both of us looking at the ceiling fan above us wondering what had just happened.

"Can I see you in your panties?" he asked me and I came shooting back to reality.

"No way, you'll just make fun of me" I snapped back.

"No, I really liked them and it's how I finally knew you might like me the way I like you." Wow, Spencer Baxter had just told me he liked me in the same way I liked him. Damn this was a wonderful night. Could it get any better?

I blushed again a few different shades of red that I missed the first time and giggled that I couldn't do it. He begged a little and before I knew it I was standing in the room with Spencer kneeling next to me with my shorts at my ankles. I was very embarrassed as he stared at me with my prick straining to be released from my satin panties and my white T-shirt straining to cover all of it. He smiled at me and told me how sexy I looked and he asked if I liked wearing other girls' clothes.

I thought for a second and finally admitted that I on occasion enjoyed wearing some stuff. I was not ready to admit that I had a locker full of clothes at home and dressed almost every night. For some reason I figured if he knew this he would think I was a freak but if I said occasionally it would be okay.

He smiled really big and asked if I'd dress up for him. His older sister had left a bunch of clothes when she moved out and when the family moved to this house, they were stored in cabinets in their basement. If I wanted to try them on he'd love to see me in them. I giggled a little and shook my head okay. This was turning into one weird evening but I loved it.

I didn't know Spencer even had an older sister so we talked about her on the trip to the basement where I also found out they had a completely fixed up basement with a family room and TV down there, a pool table, bar and an extra bedroom for guests. I guess this is where his sister would stay if she came back to visit because I didn't see an empty bedroom upstairs.

He led me to their storage / laundry area and opened up two big steel cabinets full of girl's clothes. They were all hung very nicely and they were all very stylish. Spencer told me to slip anything on that I liked but I had to model for him. Seemed like a fair enough deal as long as he didn't make fun of me after I got dressed up. I figured after the way he had just kissed me there was very little chance of this happening.

I looked through the outfits and finally found a beautiful blue satin dress that I'm guessing his sister must have worn to her prom or something. It was dark blue satin with princess sleeves, narrow at the waste and full at the bottom. I quickly got out of my shorts and T-shirt and carefully slid into the dress. I unzipped the back and stepped into the body of the dress, slid it up and carefully zipped up the back. The dress fit a little big on me but felt wonderful. I loved the way it was tight around my waste and yet scooped down in the front. I was glad I had my panties on but I really wished I had a pair of nylons and shoes to wear with the dress. I looked around the laundry area and around the cabinets but wasn't able to find anything. I kept swooshing with every step and I was just sure Spencer could hear me walking around. I fixed up my hair a little bit, combing my fingers through it to make it look a little more presentable. I patted the dress so the folds in the material were set correctly and I tried to fix the waist and sleeves so they were straight. I tried to make myself as acceptable as possible before making my modeling debut. Spencer finally yelled from the other room that he was ready so I walked out into the family room they had set up.

Spencer was lying on the couch waiting for me and looked very handsome. I walked out and did a little twirl for him smiling and blushing, hoping he would like the look.

Spencer stared, smiled and his mouth dropped open. He jumped up, walked over to me, put his arms around me and gave me a big hug. He whispered in my ear that I was the most beautiful thing he had ever seen and wished we had done this at the beginning of the evening. There was music on the stereo so we sort of slow danced to the slow beat. I had my arms over his shoulders and around his neck and Spencer ran his hands down my hips and over my butt. He explored my body with his hands and I enjoyed every second of it. Occasionally I could tell he was just as excited as me because he'd brush his hips against me and it felt wonderful feeling the bulge in his pants. It felt heavenly having him feel my body as I swayed my hips to the music.

After a few minutes of dancing, Spencer leaned in and gave me a slow kiss on the mouth. We slowly turned our heads and kissed each other passionately, Spencer offering me his tongue and me accepting it into my mouth with a slight nibble and suck on the end of it. His hands continued to explore my body and occasionally slid in front feeling my hard clit as he called it. I tried to tuck it firmly between my legs when I put the dress on but it was getting so hard there was no way the panties were going to hold it down. Spencer sucked on my neck and it drove me absolutely nuts standing there together. He nibbled on my ear lobe and whispered that he was really getting hot and wondered if I wanted to sit on the couch?

We slowly moved over to the couch and Spencer made room for me by tossing all the pillows on the floor. I sat down with as much grace as I could, crossing my legs and flattening out the dress so that it lay nice and flat. Spencer sat next to me and leaned into me kissing me on the mouth, nuzzling my neck and feeling my chest, slowly running his hands down my hips to my legs. I enjoyed rubbing his chest and feeling the muscles in his shoulders, knowing he was in charge of both of us. He slowly opened my legs and knelt on the floor in front of me. He slid his hands up under my dress, feeling my legs and separating them slowly. We stared into each other's eyes and he told me how beautiful I looked. I blushed again and told him he was very beautiful also but that I was very nervous. He winked at me and leaned down under my dress and kissed me on the inside of my thigh. He had pulled my dress up, exposing my bare legs. I wished again I had nylons to wear for him but he seemed to be fine without him. He slid his head down and started kissing me on my clit through the panties. I gasped with nervousness and excitement and knew right then this is what my life had been missing.

I sort of readjusted myself so that I was a little more comfortable and Spencer took the opportunity to pull down my panties so they were on the floor. I wanted to take them completely off but he left them around one of my ankles because he thought it was sexier. He went back down and started kissing me again; I ran my fingers through his hair and guided him to my groin. He started kissing my thighs but I couldn't see his face because the dress was full around my stomach where he had bunched it up. He pulled back and told me how beautiful it was, all shaved and pretty. I'm sure I blushed again but I just sort of ran my hand through his hair and enjoyed the complement. He smiled at me and went back under the dress.

I leaned back as he took the tip of my penis in his mouth and started sucking on it. I thought I was in heaven as he slowly kissed the underside of the shaft and licked his way back up. When he finally took it fully into his mouth I thought I was going to explode it felt so wonderful. He cupped my balls with one hand as he quickly went up and down on my penis with his mouth, making it slick and moving faster with every turn. It didn't take long and I knew I was going to explode and tried to pull out of his mouth because I wasn't sure if he really wanted me to cum in his mouth. He clamped onto my legs with both hands and kept his mouth tight around my shaft as I exploded deep into his mouth. All the times I had beat off in my room alone it never felt like this. The feeling was so explosive that I moaned out his name and couldn't keep my hips still. I bucked on the couch pushing my dick down his throat and somehow he kept sucking on it. I finally started to regain composure and looked down to see Spencer smiling at me with cum dripping out of his mouth.

I sat there for a minute trying to catch my breath as he moved up on the couch next to me. I looked over and he was staring at me smiling, looking at my body, running his hand through my hair, and brushing it away from my face. I smiled at him and he said it was his turn.

I tried to get up so that I could also get on my knees but he pushed me back down. He smiled and said he wanted to fuck me up the ass. Never had I thought this was going to happen and never did I anticipate this is what he was going to want. Fear went through my body because I had tried putting my finger up my butt once before and it sort of hurt, but what would a penis be like up there? I sort of smiled and told him I didn't know if I could do that and he told me not to worry, he would be really gentle and we would go really slowly. Nothing had gone slowly this evening so why should I ever think this would go slowly?

I asked him if I could kiss it and look at it and he quickly unbuckled his jeans and slid them off and pealed off his shirt. He slid his white briefs off with his jeans and I stared at his beautiful penis and naked body. His penis was much bigger than mine, probably a full 6 inches standing there and I just had to touch it. I moved my hand over it and gripped it by the shaft. I slowly moved my hand and precum was leaking out of the head. I leaned over and took the tip in my mouth tasting the precum as I slowly slid my hand up and down the shaft. I guess I was hoping he would explode now but instead he pulled my head away. He whispered "not yet" and got up off the couch and ran to a bathroom. I watched his dick go bouncing across the room, hard as a rock and shiny with my spit. He came back very quickly with a big tub of Vaseline and I knew he was serious. I had serious reservations or should I say fears? I wanted to say no but there was no way I could at this point because I didn't want to make Spencer mad at me.

I asked how are we going to do this and he said he had seen it once on a video between a man and a woman. He got me into a kneeling position on the couch with my head down near the armrest. He lifted the dress over my ass and laid a big part of it on my back and started massaging my butt cheeks. I felt really exposed but I enjoyed the attention he was giving me as he slid a hand between my legs and played with my dick. He kissed my butt cheeks and continued massaging my legs and ass. It didn't take long and I looked back to see him taking a big glob of Vaseline out of the tub and plopping it on my butt hole. He spread my cheeks apart a little but this was a massive amount of jelly. It was cold and slid between my cheeks and made me feel even more worried. He took what was left on his hand and rubbed it on his penis. I smiled a very nervous smile and he told me it would be wonderful.

I put my forehead on the armrest of the couch as Spencer climbed onto the couch right in back of me. I was very worried as he slowly inserted a finger in my ass. It was very tight and sort of hurt but he slowly moved it in and out and really lubed me up. I could hear the action and the Vaseline making a sucking sound in my butt hole and I became a little less worried thinking with all this lubrication maybe it wouldn't hurt too bad. It took a few minutes but it started to feel okay when he tried sticking in a second finger.

I must have tensed up a little because it really started to hurt but Spencer went slowly. After a few more minutes the pain was going away and he took his fingers out. I figured maybe he was done but instead he moved in closer. I could feel his hairy legs against my smooth skin as he positioned himself to enter me, grabbing my hips with his strong hands. I felt his penis head against my hole and he slowly moved forward, using his body weight to force his way into me. Again I must have tensed up because it really started to hurt. It felt like my butt was being split in half as he slowly entered me. He went slowly but my butt felt like it was on fire when he finally bottomed out in my ass. He had a hand on each of my butt cheeks and gave out a small moan as he realized he was all the way inside of me. I couldn't imagine this ever feeling good but by his moan I could tell he was enjoying the feeling.

Now I knew I loved Spencer but this was taking it to the limit. He slowly started sliding in and out taking very short slow strokes. The more he moved the more it hurt and the more I wished he would be done. I was just sure I had to be bleeding but he didn't stop. I cried a little into the armrest and wished it would all stop. After about 30 second it all started to feel a little better as he stopped what he was doing and just knelt there. I turned my head around and asked if he was done and he told me he was just resting for a second. Resting??? What the hell did he have to rest about? He started to continue and this time it didn't hurt nearly as much. The lube must have been working better because he actually started to feel a lot more normal and then he started bucking his hips faster. The pain returned but it didn't take long and he was starting to cum in my ass. I sort of helped him along by moving my hips to greet him and he let out a soft moan when he finally let loose. I could feel his entire body spasm and his cock let loose with a stream that filled me completely. I knelt there with weak legs, sore ass and sore arms from attempting to hold myself up and he slowly slid back out of me. He sat on the couch with his still hard cock jetting up for his groin. I smiled at him and he gave me his shirt to sit on. I positioned it under my butt and sat next to him, putting my head on his shoulder and wondering if he loved me as much as I loved him.

We sat there a long time, goo running out of my ass and Spencer telling me how wonderful it was inside of me, attempting to explain how it felt. I agreed with him completely even if it did feel like my butt was broken. He got up and went into the bathroom to clean himself off. I sat there alone thinking how wonderful this evening was and when he returned he asked me if I wanted to try a different dress on. I said no and that I better get cleaned up before we did anything else. I stood to go to the bathroom and could feel goo running out of my butt cheek and down my leg. I hated the feeling and loved the feeling at the same time. It was sort of disgusting knowing what it must all be but also made me feel wonderful, like a girl. I put his shirt up to my butt and made a run for the bathroom. I was careful to keep the dress clean and sat on the toilet letting it all drain out of me. I smiled to myself that I wasn't a virgin any longer and that this was a wonderful evening. After a few minutes Spencer brought me my underwear so I finished cleaning myself up, put my panties back on and made my way out to the family room. I must have looked like a mess, still in the dress and now walking funny because Spencer let out a laugh. I laughed with him but told him it was entirely his fault my ass hurt so badly. He hugged me and told me how wonderful it was and that he would never forget this evening. I hugged him back, changed into my shorts and T-shirt and we cuddled on the couch. We woke up in the morning, had some cereal for breakfast, made out on the couch some more and promised to do this again really soon. Little did I know how soon it would be when he called me that evening.

  

  

  

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