Ashley's Summer Experience free porn video

Ashley's Summer Experience - By Ashley Taylor It was the summer break after graduating high school and before beginning college. My parents had put enough money aside that I didn't have to work, so I was just enjoying the summer, spending time at the lake and hanging out with friends. My best friend was Julie, a totally gorgeous girl except for one thing; she was totally flat chested. I mean flat as a board, but she was so pretty that it never really hampered her in the dating department. We had been friends, forever, well since about the 7th grade. I never really understood why. When we met I was an over weight, extremely shy guy, but for some reason we just clicked and started hanging out. I said I was overweight, however, during my senior year I was in a car wreck and had to have an operation. I was in the hospital for about 6 weeks and during that time I lost all of my excess weight - well most of it. I loved it - I was mostly skinny for the first time in my entire life and it gave me confidence I never had before. I was still extremely shy, but wasn't feeling fat anymore. As I mentioned I was shy - in fact, I had just graduated high school and still hadn't gotten laid yet. Oh sure, I had been out on dates, but I was too shy to move beyond a peck on the cheek. Well it was two weeks into the summer and I get this call from Julie. She said her mom was out of town and wanted to know if I wanted to stop by and hangout. Of course I did, I didn't have anything else going on. Julie's mom was divorced and made out very well in the settlement. They had a swimming pool and a really big house. After the divorce, Julie's dad took a new executive job in Maryland and moved away. So it was just Julie and her mom, and Julie's mom spent a lot of time in Texas looking after Julie's grandmother. Anyway, when I got there, Julie was out by the pool in a very sexy and revealing thong bikini rolling a joint. I said she must be in the partying mood. Which if you knew either Julie or I at this stage of our lives, partying wouldn't have surprised you. We took every opportunity to grab a buzz. Well anyway before you knew it, we were both stoned. She said, "Let's take a swim," at which point I had to remind her I didn't have a swimming suit. She said I could borrow one of hers and she dashed off to her bedroom with me following closely behind. She pulled out this very sexy black one-piece suit that had built in push- up padding and high-cut sides. I said, "I can't wear that!" To which she responded, "Why not you certainly have more up top than I do!" I said, "What if someone sees me?" She said, "Don't be silly no one else is here and besides, you might actually like it!" I said don't count on it and she just smiled. I mentioned that I had lost almost all of my weight, well part of what I didn't loose was on my chest. I'm just one of those guys that have a lot of flesh on my chest. Well Julie insisted that I put on the suit, so I took it into the bathroom and pulled it on and put straps over my shoulders. Julie came over and pulled the top out and gathered up all the flesh on my chest and put it in the underwire cups of the swimming suit. Julie stood back and said, "Damn I wish I had tits like that!" Julie then insisted that I tuck my penis back between my legs as this created a nice v-shaped flat front. The back of the suit had this really defined seam that went right up the crack of my butt. It was intended to lift and provide some sexy definition, and it was definitely doing its job. Both Julie and I couldn't believe how feminine the suit made me look. Then Julie said, "I got an idea!" and I saw that look on Julie's face. She said sit down over here at my vanity and let me try some things. Julie started rubbing some foundation onto my face. I never had much facial hair and what I did have I shaved off that morning. After the foundation she added blush, eyebrow pencil, mascara, eye color, lip liner, and then she painted my lips with a rich red color. Then she said, "Hold on a minute I'll be back." She came back carrying a short sassy medium brown colored wig, when she put it on my head it looked pretty close to the cut Jamie Lee Curtis wears. She then painted my finger and toe nails the same color as my lipstick. Julie then said, "I can't believe it, you are gorgeous!" As I looked in the mirror, I had to agree. I was beautiful. I had perky breasts, a cute face, and my ass was to die for. Julie said, "I have a great idea! Why don't you hang out all weekend as my girlfriend?" "What? Are you nuts? I can't go around like this, what if somebody sees me?" Julie said, "Look we need to talk." She went on to say, "I know you like this, I know you've wanted to dress like a girl for a long time. Don't forget who you're talking to, I'm your best friend. I see your face light up when we walk by the Victoria Secrets store at the mall, or when you read the ads in Sunday's paper and stare at the bra ads. I see you pick up and read my cosmos even though Sports Illustrated is sitting right next to it. I hear your comments about what that girl is wearing or that other girl has too much make-up on etc? And I saw your face when you just looked in the mirror after getting all made up ? the look says it all. These are not things a guy does; these are things a girl does. And guess what? You are still my best friend and will always be my best friend!" I couldn't believe my ears; Julie had pegged me dead on. I always wanted to be a girl, I wanted to dress in tight dresses and have big breasts and wear high heels, and she had guessed it all! She was right and she knew it. So I told her everything she said was true. I have dreamed about being a girl ever since I remember and I would love to hang out as her girl friend all weekend. She said, "OK, now we still have a couple of other things to do." Julie had me take off the swimsuit, and she put shaving cream on my legs, chest, and armpits. She then helped me shave off all of my body hair, my freshly shaved body felt nice and cool. She then grabbed some medical tape and taped back my penis to ensure it stayed out of the way. She then put one of her mother's waist nippers around my middle and placed it on the tightest setting. "Just to give me a little shape," she said. Julie then had me get the swimsuit back on and she pulled my chest flesh back into the under-wire cups and gave me a little tweak on my nipples, which totally turned me on. We then went and found a pair of Julie's shoes; they had a 4-inch heel, ankle strap, and were open toe. She had me slip them on while she put on a pair of 5-inch 'cum fuck me' pumps. We both looked very sexy in our swimsuits and high heels. She then gave me a gold bracelet to wear and grabbed a couple pairs of earrings. "This way," she said and off to kitchen we went. She had me sit down on one of the kitchen stools and placed an ice cube on my earlobe, I knew what she was doing and I didn't say a word. She pierced both of my ears and inserted a pair of gold, dangling earrings. Now, let's make a pitcher of margaritas. It was about 2:00 o'clock in the afternoon and we had already drank three margaritas each, and smoked another joint. We were just lying on the lounge chairs near the pool enjoying the sun, when we heard the gate open. Julie looked up and said, "Hi John, Hi Danny, what are you guys doing?" John said, "We were just driving by and I thought I saw your car, so we just stopped to see if you were around." John and Julie weren't boyfriend and girlfriend, but they liked to have sex on a semi-regular basis. Julie looked over at me and could tell I was mortified, so she turned to John and Danny and said, "Have you guys met my friend Ashley before?" They both said no, but they were glad to meet me. In turn, I said hi and tried to smile best I could given the circumstances. John then announced, "Hey I just picked up some killer weed. This stuff is unbelievable; it's the best stuff I have had in years. Do you two want to smoke a joint?" Julie said sure, but lets all move over to the patio. On the patio, there was a wicker couch and loveseat. Julie sat on the loveseat and John sat down beside her. I sat on the couch and Danny sat down besides me. While John rolled the joint, everybody tried to make small talk. Danny said, "That swimsuit looks incredible on you." I smiled and said, "Thanks, but it's Julie's suit I'm just borrowing it." He said, "Maybe you should keep it, it really looks good." By this point John had lit the joint and passed it to Julie, Julie then passed it to me and I took a deep drag on it and held my breath, and passed it on to Danny. As I let out the smoke I felt a wave of pleasure fell over my body. Every part of my body was tingling, but nothing more than my nipples. They instantly turned hard and were yearning to be touched. I said, "That is incredible pot," in my best girl voice. I looked over and John was giving Julie a shotgun, that's where one person puts the lit end of the joint their mouth and blows smoke into the other's person's mouth. John then passed the joint to Danny and said, "Give Ashley a shotgun." Danny leaned over and placed his hand on my thigh and started blowing smoke into my mouth which again I held in for as long as I could. Well, Danny just left his hand on my thigh and I looked over and John had his hand on Julie's leg as well. We finished the joint and everybody was really stoned, and I don't know about anybody else, but I was horny as hell. Julie got up and said, "Let go make some more margaritas". So we all headed for the kitchen. As I walked to the kitchen, I could feel Danny's eyes on my ass, the 4- inch heels gave my ass a sexy sway or it could have been that I just wanted to give him a little show. Julie asked me to grab some clean glasses from the cupboard and as I turned to get the glasses, Danny put his arms around me from behind and kissed me on the neck. He said, "You are incredibly sexy, I just can't help myself". I just stood there for a minute letting him kiss me on my neck; it just felt so good. I took a quick look over my shoulder and saw John and Julie in a similar embrace and I just said to myself what the hell. I could feel Dannys cock getting hard against my ass as he continued to kiss my neck and roam his hands all over my body. His hands finally reached my nipples and he squeezed them and I thought I was going to have an orgasm right then and there. I let out a loud moan and said, "Oh, Danny baby that feels so good!" I then heard Julie say, "John let's move to the couch," and I told Danny that sounds like a good idea. I turned around and gave Danny a deep kiss and reached down with my hand and stroked his cock through his pants. When we reached the couch Danny continued to kiss me and play with my nipples, he then reached for my hand and placed it on his cock. I started to rub up and down on his cock through his pants and he reached down and undid his pants and pulled out his cock. I looked over at Julie and she was already giving John a blowjob. I reached down and started stroking it with my hand, and Danny whispered in my ear, "kiss it baby, kiss it." I looked over at Julie again and slid down to my knees and started to lick the head of Danny's cock. Compared to my penis it was huge. It was almost 7 inches long and a lot thicker than mine was. I licked up and down the shaft and placed the head into my mouth, then back up and down the shaft with my tongue. Then I heard Danny say, "Suck it baby." I then placed his cock in my mouth and started bobbing up and down taking about three inches at a time. I was continuously swirling my tongue on the bottom side of his cock. Danny said, "Take more," and I tried to take as much as I could with out gagging, and Danny said, "That's it baby, that's it." I was really getting in to it, when I heard John say, "Julie I'm coming baby?here it is baby, here it comes!" And out of the corner of my eye, I saw Julie really bobbing up and down. Then Danny was saying, "Here I go, here I go?Oh Ashley here it is!" And Danny shot his cum into my mouth, it was hot and salty, and tasted really good, I swallowed all of it. I continued to suck on his cock until it got soft and he pulled out. Danny leaned down and kissed me on the cheek and said, "That was incredible!" At that point Julie stood up and said I'm ready for that margarita and everyone said that sounded good. As we were standing in the kitchen, John said, "Hey why don't the four of us go out dancing tonight?" Julie said, "That's a great idea, why don't you pick us up around 9:00 tonight and we can go to the red room." Both John and Danny said, "Great, but we need to get going right now." Danny gave me a goodbye kiss and John gave Julie a kiss and they said see you at 9:00. When they had left I said to Julie, "What have you gotten me in to?" Julie said, "don't start that crap with me, you're the one that said you have dreamed about being a girl for ever. I just presented the opportunity to live your dream and you didn't hesitate at all, did you? That's what I thought. Now, I just have one question for you, Don't you just love the feel of a hard cock in your mouth?" I just smiled and told her that when Danny came, I had cum too. I didn't even touch myself. I was just so turned on and Dannys cock is so big and when he started shooting his cum into my mouth, I felt my cock release some cum too. Julie leaned over and put her arm around me and said, "This is the real you, you're a beautiful and sexy woman that apparently loves big cocks!" I said, "I know and I just loved what happened!" Now she said, "We have a lot to do before 9:00, let's go upstairs and get changed, we need to do some shopping." When we reached Julie's room she had me take off the heels and swimsuit, leaving standing there in the waist nipper with my penis still taped back between my legs. She gave me a pair of high cut thong panties, a seamless underwire bra, a pair of Lycra capri pants, and a deep v-neck silk blouse. I pulled on the panties and loved the feel of the thong strap going up my butt cheeks. I then I put on the capri pants which came to about mid-calf, and attached the underwire bra and pulled my flesh into the cups. I was about ready to put on the blouse, but Julie said wait a minute. She came over and slipped a pair of silicon breast enhancers into the cups of the bra and positioned them to create maximum cleavage, it also increased my bust size about a cup ? I was now a very full B, maybe a small C. She said, "The enhancers would provide a good size for me until something else could be done with my natural breasts." I pulled on the blouse and looked in the mirror; everything looked good ? just needed a little repair on my makeup. I was about to put on the heels I had on earlier, but Julie gave me a pair of black wedges with a 4" heel, she said they would look perfect with my outfit. So I put them on and she was right! As I looked in the mirror I looked very sexy and I loved it. Julie finished getting dressed and said let's go! As we drove along I asked Julie where we were going. She said, "We have three stops, the first one was a foundation shop." She said I needed better curves than the waist nipper could provide, the other two stops we would talk about later. When we got to the corset store, Julie talked to the owner and I was whisked into a fitting room and told to strip down to just my panties, but leave my heels on. The owner came in and took several measurements and came back with a lovely white satin corset. The corset was open busted and laced in the back. She placed the corset around me and asked me to hold it place while she laced it snug. She then asked me to grab this bar that was above my head while she started pulling the laces really tight. After she worked on the lacing for about 5 minutes, she told me to drop my hands and turn around facing her, she then started to pull the flesh on my chest up and out over the open cups. She worked on this several minutes and then had me turn around again, she tighten the laces on the upper half of the corset very tight and then finally proclaimed that she was done. When I looked in the mirror it was amazing. The open cup corset had taken all of the loose flesh on my chest and formed it into breasts ? as I turned sideways and looked in the mirror in looked like I had solid B cup breasts, not huge but not small either. And they looked perfect with my now very nipped waist and made up face. Julie just said, "Incredible! You are one very lucky girl!" I slipped on my blouse and was feeling my breasts through the silk, but I noticed Julie in deep discussions with the owner ? about what I wondered. Julie paid and said let's go. The next stop was the nail salon just two doors down, where once again Julie had me whisked to a station. The lady asked how long I wanted my nails; I looked at Julie who said about 1/4 inch. The lady removed the existing nail polish from my nails and prepared to put on the extensions. I was thoroughly enjoying the atmosphere of the salon and engaged in small chitchat with the nail tech. We talked about everything. I found out that she was getting married in about 4 weeks, it was going to be a fairly big wedding, and that her sister was going to be her maid-of-honor. Of course, I told her that I had a date that night and that we were going dancing at the Red Room etc. you know girl talk. Well before I knew it my new nails were being painted the same color as my lipstick and I was done. I asked Julie where to next and she said, "Wal-Mart." "Wal-Mart?" I asked. As we walked to the car in the parking lot I was acutely aware of my breasts moving and particularly my nipples, rubbing against the silk blouse. It was very sensual and getting me into a very horney state. When we got to Wal-Mart I asked Julie what we were going to get, she said you'll see. So I was little surprised when we ended up in the kitchen section. She said, "Ah, there they are," and grabbed two large sized clear funnels. But these funnels were a little different, instead of a true cone shape they were more rounded. Julie then trod off to the camping department. She then picked up two electric pumps used to inflate and deflate large air mattresses. I asked what in the world were they for. She just smiled and said, "You'll see." Julie paid and we were headed back to her house. When we got home, she said come in here and take off your blouse, which I did. She told me make myself comfortable, so I sat down in the recliner. She then pulled out the two electric pumps and set them on the deflator setting, then attached a funnel by the small end to the hose on each on each of the pumps and secured in place with tape, she then applied Vaseline to the mouth of the funnel. She then placed the mouth of the funnel against my one of my breasts and pushed all the loose flesh underneath the lip of the funnel. She then turned on the electric pumps power and all of the loose flesh got sucked into the funnel. The suction immediately created a seal and started pulling the flesh into the cup of the funnel. The longer the pump sucked the air out of the funnel, the more my flesh filled the cup of the funnel. She then repeated the same process for the other breast. Julie explained to me that the constant suction would stimulate the flesh and cause it to expand. She told me the flesh would return to it's normal state after about 12 hours if the suction was discontinued, but for now just sit back and watch some TV, you're going to get suctioned for about the next three hours. I was amazed as I watched my flesh being pulled into the clear cups of the funnels...and sure enough I could tell the flesh had expanded after about 15 minutes. I was amazed and very turned on at watching my breasts being shaped by the suction. At 8:00, Julie said ok that's enough it's time to get ready. She turned off the pumps and pulled off the funnels, and what was left was very full breasts with very sensitive nipples. Just brushing them was a turn-on, not only did the suction create more volume, but it also increased the sensitivity of my nipples. Julie said, "Let's get you dressed." Julie handed me a short black leather skirt, sheer black thigh high stockings, and a cream color silk blouse. I took off the Lycra pants, and put on the stockings attaching them to the garters from the corset, then pulled on the skirt, then put on the blouse, then had Julie zip the skirt up in back. Julie then handed me a wide belt that I placed around my mid-section. I slipped on the same 4- inch heels I was wearing earlier in the day. Julie sat me down and reapplied my makeup ? I was ready for my first date. Julie got dressed in a similar outfit and we were ready to go. The doorbell rang and I started to get a little nervous, Julie sensed this and told me not to worry that I looked great. She open the door and John and Danny came in, both were dressed in khakis and button down shirts ? they looked very preppy and very handsome. We offered to get them a beer and they agreed and John of course pulled out a joint of that killer weed and we got stoned. Julie finally said, "we should probably get going," so we left in John's car with Danny and I sitting in the back. We made small talk and he placed his hand on my thigh and leaned over and kissed me on my neck, which of course sent ripples through my body! That weed had heighten my senses and especially in my nipples. As we drove to the club hitting the little bumps in the road caused my nipples to rub against the silk blouse and it was really getting me turned on! We got to the nightclub and the boys paid for us to get in. We found a table close to the dance floor and ordered a round of drinks. Julie and I were drinking cosmopolitan martinis and the boys were having beers. After several drinks, my nervousness was gone and I was really getting into my date. Danny and I were having a great time and after a while he pulled me to the dance floor. We danced a couple of fast songs and then a slow one came on and Danny pulled me close. We were both pretty tipsy by this time and as he pulled me into his body he gabbed my ass and I could feel his hard cock against my waist. He looked into my eyes and said he was having a great time, then he kissed me deep and I kissed him back very passionately, and told him I was having a very, very good time as well. He kissed me again and then said, "Let's find Julie and Jeff and let's get out of here!" I agreed. We found Julie and Jeff and left the club. On the way home, Danny couldn't keep his hands off me. He was kissing me and fondling my breasts and tell him how sexy I was, and I was totally into it. I felt so sexy and feminine and all I could think about was making love to Danny. We finally reached Julie's house and Julie and Jeff immediately went to her room, so I took Danny to the spare bedroom. Danny was all over me, but I said, "Wait, I have to tell you something!" He said, "No you don't, Julie called me this afternoon and told me all about you." "What?" I said. He said, "Don't be upset with Julie, she was just being a friend to both of us. See, about 6 months ago Julie and I got really drunk and I told her my secret fantasy was to make love to a she-male. I didn't know you were a transvestite yesterday at all. It wasn't until Julie saw that we were both extremely attracted to each other that she thought it would be ok to let me in on your secret." My head was reeling; I was shocked, but very relieved. Danny was turning out to be more perfect than I could have imagined. Then Danny said, "Just lay back and let's enjoy each other," and then he kissed me deep and passionately. I surrendered. Danny undid my blouse and started sucking my nipples it was unbelievable. I was getting so turned on! I reached for Danny's belt and unbuckled it, and then pulled his pants down and said, "Take'em off lover!" I then grabbed his beautiful cock and started stroking it. Danny took off my blouse and skirt, leaving my corset, thigh-highs, and heels on. He told me to roll over, which I did. He then started to lick my anus, which totally drove me crazy. He then leaned down and told me he wanted to make love to me. I grabbed the KY jelly that Julie had conveniently left on the nightstand. He squeezed a little bit on to his finger and inserted into my backdoor pussy. I was so tight, but he started to work it in and out. And then pretty soon, he inserted another finger and it really felt good. He then whispered okay baby, I going to stick my cock in now. I felt the head of his huge cock against my backdoor pussy and I really wanted it bad. So I pushed back against his cock and he pushed into me, and the head of cock popped into me and I screamed in pain and pleasure! It hurt so much, but felt great all at the same time. Every part of my body was tingling all over, especially my nipples. He told me to relax and he let me get used to his cock being inside me. He told me how incredibly wonderful I felt, and I told him how big he felt. He reached around me and started rolling my nipples between his fingers and gently tugging on them, while he was kissing my neck. It was very erotic and I was turned on more than I could ever remember. Finally the pain subsided and he started moving his cock in and out of my ass. I started getting into the rhythm, moving back against him and driving his cock deep into me. After a few minutes, Danny had really picked up the pace and I was matching his motion stroke for stroke. I was so sensitive and so turned on; my body was on fire ? like little bits of electricity running all through my body. Danny started talking to me, "That's it baby, oh yea, God you're a good fuck, your pussy is so tight, that's it baby, oh yea!" Then Danny really picked up the pace and was ramming his big cock in and out of me hard and his balls were slapping against my ass. Danny starting saying, "Oh here I come, here I come, Oh baby!" At that moment Danny tensed up and I felt his hot cum pumping deep into my ass. This sent me over the edge, and my little cock started spurting cum at the same time. We both orgasm at the same time and almost in perfect sync, Danny wasn't moving anymore and I could feel his dead weight on me, and I felt like a true woman having brought my man to such a great orgasm. Danny said, "Ashley that was the most incredible sex I have ever had!" He then kissed me on the neck and he fell asleep. After a few minutes I feel asleep too. I felt someone shaking my shoulder and saying, "Get up, get up Ashley". When my eyes finally adjusted I could see that it was Julie. I asked, "What are you doing?" She just said, "Get up and come with me." Once we got in the living room, I asked what was going on? She said, "It is 6 o'clock in the morning and that I needed to get cleaned up." "What in the world are you talking about?" I asked. She said, "Look, you need to get cleaned up, you don't want to have Danny see you as anything less than a beautiful girl, at least during the first few weeks of your relationship. So let's get you into the tub, into clean clothes, and fresh makeup, before he wakes up." I looked in the mirror and finally understood what she was talking about. I was still wearing the corset, the thigh-hi's (which were totally a mess), and I still had my heels on. My makeup was a complete wreck. So off to the bathroom I went with Julie tagging behind. Julie helped me take off the corset and started a bath with scented oil, and I slipped in. Julie sat on the toilet and wanted to know every little detail, so I told her what happened. You could tell by the look on her face, that she was really happy for me and you could tell I was on top of the world by the sound of my voice. I washed up, shaved my legs and underarms, and trimmed my snatch hair, then got out of the tub. Julie applied my makeup, put the waist nipper on me, and gave me a pair of thong panties to put on. She then told me we were going to aerobics this morning, so she laid a set of exercise clothes. But first, you need to suction your breasts, so we attached the pumps and let them run for about 1-? hours, and they did their magic, my breasts were sucked into the cones and the flesh expanded. I then put on an underwire bra, a pair of hot pink Lycra capri tights, a white thong uni-tard, and a white pair of tennis shoes with pink strings. Julie had gotten into the shower and was dressed similar except she was in blue tights and a yellow uni-tard. We woke up the boys and told them it was time to go. Danny was all over me, kissing me and saying, "He had to see me again. How about tonight?" I looked at Julie, and Julie said, "How about you guys coming over for dinner tonight and we'll rent a video?" They said they would be here and we kissed them goodbye and sent them on their way. Then Julie said, "Come on girlfriend, let's go or we're going to be late for aerobics!" I was so excited as we walked out the door; I was on my way to another new 'girl' experience. Hoped you enjoyed this little story, if you liked it please email me at: [email protected] Huggs and Kisses, love Ashley