Unexpected fun with an online friend
A little after my 27th birthday, in early spring of 2007, my sisters and I were occupied planning our parents 30th wedding anniversary party. For the week leading up to the day, my dual focus was my job and planning this party. On this Friday night, we have finally arrived at party date. My sisters and I successfully managed to surprise our parents with 50 of their closest friends and family. The party was a great success and my sisters and I finally got to relax and enjoy the night.
Fast forward to the party’s end and I am very very buzzed. By the time my sober sister decided to drive me home, all I could think of was going to my bedroom and falling asleep. I was exhausted. My sister dropped me off and I enter my apartment and immediately strip down to my blue briefs and go to bed. As I laid down trying to sleep, my mind starts to wander as it usually does. After a little while of this, I relent and raise up from my pillow and lean to my nightstand to grab my laptop. I lean on my side as I go to my favorite porn site and find a very sexy video of an older gentlemen having fun with a crossdresser in white lingerie. I started to get more and more turned on as I watched. My buzz and this video changes me from wanting to sleep to wanting to play. About 15 minutes through the 40+ minute video, I get up from my bed and slide off my blue briefs to expose my hard, completely smooth, 6 inch cut cock. I go to my closet and go to my secret section, where I keep all of my lingerie and outfits that I like to wear when I’m alone or with a friend. Rummaging through my closet, I find a pair of black seamless pantyhose and a leather teddy and slide those on. Before leaving my stuff, I reach into my storage box behind my outfits and pull out a thick, 12 inch, flesh colored dildo out with some lube and climb back into bed and continue watching.
I lay on my side and slide my dildo under my black pantyhose and slide it into all the way into my smooth hole. I squeeze my cheeks curate back and forth as I turn on the vibrate function and begin to immediately shake as I slowly rub my leaking nylon cock while my eyes are fixed on the screen, watching this attractive older man slide is cock in and out of a beautiful crossdresser in white lingerie. The feeling of my hose on my legs and the large vibrating dildo inside of me, begins to send waves down my body and I begin to have a massive prostate orgasm. For a good 2 minutes, I lay on my side shaking and moaning as my cock leaks through my hose into my bedsheets. This drove me to another level. At this point, I need the real thing.
I make my way to my email and **********. I didn’t have a regular bud at this time and have, on occasion, ventured to ********** to see if I can meet anyone. Usually unsuccessful when on there, I didn’t really think I’d meet anybody but you never know. However, as I open my email, first email down was from a friend I had recent met online named Randy. A few weeks earlier, Randy and I met on a men’s web chat site that was popular at the time. He was married and in his mid 40s and like me, he had a pantyhose obsession. We had exchanged pics via email and chatted a dozen or so times and always had a fun time. He is a total top and since I’m a bottom, we were a match made in heaven, online at least. He lived about 30 miles away, so our relationship was strictly online, but we did chat about hopefully some day meeting in person. I was single and had my own apartment, so I could host discreetly if he could ever sneak away. I grow excited as I see his email address in my inbox and open the message.
I see the message was from two hours prior, in which Randy tells me that his wife is away for a week and that he’d love to chat again soon and hopefully meet while she was away. We hadn’t chatted in a week since I was so busy with the party and was happy just to see his email and that he was still interested. I smile and immediately hit reply and tell him what I’m doing and what I’m wearing and tell him he can come over any time he wants. It’s 1am so I’m expected maybe a response tomorrow morning earliest. Luckily, I receive a immediate response. Randy wrote “mmm that sounds so sexy, maybe I can come over now and stay the night?” This response made me shiver in delight. I immediately reply, “Oh yes Randy, I’d love nothing more. Here is my address” Randy replies “Great. I had pantyhose on already so leaving now. I’ll be there in 30 lover”. I reply back to let him know I can’t wait and gave him my apt number and told him my door was unlocked and come right in!!! Xoxo”.
My excitement is through the roof. My buzz wearing off but lust starts to grow. Going off of past chats with Randy, I know he loved layered nylons and fully dressed crossdressers. I go back to my closet and slide a pair of red argyle thigh high stockings over my black pantyhose and grab for my makeup kit and long brown wig and black stilettos heels and head to the bathroom. I excitedly work on my lips and eye lashes quickly and affix my shoulder length black wig. About 20 minutes after I opened Randy’s email, I’m in my wig, makeup, heels, layered nylons, and black leather teddy. Deep down I’m hope he doesn’t flake. We never met in person before but chatted so much that I was really hoping he would arrive. After I look at myself in my bathroom mirror, I head back to my room to get my dildo and laptop and move to my living room. I turn on the light and lay on my couch as I slide my dildo back in me under my black hose and lay on my back as I watch another porn from this same actor, who I’ve grown smitten of. I’m in such lust as I suddenly hear the sound of footsteps. I live in a complex with 8 other one bedrooms and outdoor access to the building. I grow more horny as I hear the steps get closer to my apartment, knowing this is finally happening. I continue playing when I suddenly see my apartment door slowly open and I see a really attractive and fit man enter. I see that Randy is very handsome, has short blonde grey mix of hair and stubble. Randy was wearing a pair of dark jeans and a hooded sweatshirt as walks in and sees me full dressed in layered nylons. Randy smiles widely and begins to undress after he opens the door. Randy tells me “your such a hot fucker, you look so amazing.” I smile up at Randy as I pull my dildo out of my ass and pantyhose and place on the floor before me. I stand up and walk over to Randy and whisper “you are absolutely gorgeous” and we start to make out while I help off his hoodie and tshirt underneath and help him out of his jeans and see Randy’s rock hard 8 inch cut cock in tan pantyhose. Our eyes open as we kiss, my red lips carressing his. So excited that we finally meet in person after so many long and hot chats. We stand and kiss for a few minutes before Randy leads me back to my couch.
Randy lays me on my back as he climbs on top of me. I wrap layered nyloned legs around Randy’s back and squeeze him into me, as we continue making out passionately and grinding our nyloned cocks together. I can feel our cocks leak on one another’s, as Randy grinds up and down my smooth body, with my legs wrapped tightly around him, pulling him into my body. The passion builds every second we kiss and after 5 minutes of this, Randy gets up and smiles at me and says “I’ve thought about you so much, I need to be inside of you”. Randy then leans down and rips a small hole in my seamless black hose and lowers his head down and licks my smooth hole, his tongue entering me and tasting every inch of me. I lean back and rub Randy’s hair as I raise my legs and moan. Feeling his tongue inside of me drives me wild, and I moan louder. Randy gets up and kneels on my couch and rips a hole is his tan pantyhose so he can free his gorgeous 8 inch cut cock. He then gets back on top of me and bends my legs back behind me, as Randy hovers over me and kisses me again. Randy then slides his cock inside of me slowly, as I close my eyes and moan. Laying beneath Randy, I feel so incredibly hot and slutty every second I’m with him. We start to kiss, as I dangle my nyloned legs over Randy’s broad shoulders and he begins to pick up the pace. Our lips and tongues caressing, feeling all of Randy’s large cock. My moans gets louder as Randy begins to fuck me hard on my couch as I lay defensively beneath him. Randy would become more dominant as we continue as I simultaneously grew more submissive, as we could tell from me moaning “fuck me baby”.
Randy looks down and firmly grabs my neck as he pounds be harder and harder. I look up seductively when Randy gets more dominant and encourage him. He starts to slam me hard and calls me by my fem name, Savannah, and starts manhandling me on my couch as I lay dressed and moaning. The feeling of his cock sliding in and out of me, drives me wilder by the second, worshiping Randy more and more. Around twenty minutes after he first entered me, Randy starts to fuck me roughly, as I lay folded under him. My cock continues to leak though my black nylons as he thrust in and out. The sensation is so great that my cock starts to swell under my hose and I begin to shake and shoot a huge load hands free over my black teddy through my black seamless pantyhose. Randy smiles at me, startled as he makes me cum with his beautiful cock and tells me again how hot I am and to get ready for his load. I loudly moan “cum in me Randy, please please” loudly as he thrusts in and out really fasts and moans loud with me. My couch shaking against the apartment wall. Randy then let’s out one last huge moan before he plants his cock deep in me and I feel the warm sensation of his semen filling up inside my hole. I moan and kiss Randy and wrap my legs around him again as he grunts and unleashes his load deep inside of me. We kiss passionately as I hold Randy close to me. He looks at me says “wow”. I look back at Randy and tell him how incredible he is.
Randy then helps me up and we walk hand in hand to my bedroom. I take off my heels and we lay in bed together. I lay my head on Randy’s strong chest, as he rubs my head and we chat. I tell Randy “when I got him from my parents anniversary party, I planned on going right to bed. Two hours later, here we are”. Randy kisses my head and says “I’m so glad I was online when you replied. I wanted this so bad”. Randy then jokes, we were pretty loud, your neighbor might know your secret now.” I turn my head on Randy’s chest and smile “I don’t care, you’re incredible. I’ll do anything for you. Randy joked “we will see”. We chatted and little bit more as I laid in his arms for a little while before falling asleep together at around 3am. Little did I know that the rest of my weekend was about to become the most memorable in my life. To be continued……
Fast forward to the party’s end and I am very very buzzed. By the time my sober sister decided to drive me home, all I could think of was going to my bedroom and falling asleep. I was exhausted. My sister dropped me off and I enter my apartment and immediately strip down to my blue briefs and go to bed. As I laid down trying to sleep, my mind starts to wander as it usually does. After a little while of this, I relent and raise up from my pillow and lean to my nightstand to grab my laptop. I lean on my side as I go to my favorite porn site and find a very sexy video of an older gentlemen having fun with a crossdresser in white lingerie. I started to get more and more turned on as I watched. My buzz and this video changes me from wanting to sleep to wanting to play. About 15 minutes through the 40+ minute video, I get up from my bed and slide off my blue briefs to expose my hard, completely smooth, 6 inch cut cock. I go to my closet and go to my secret section, where I keep all of my lingerie and outfits that I like to wear when I’m alone or with a friend. Rummaging through my closet, I find a pair of black seamless pantyhose and a leather teddy and slide those on. Before leaving my stuff, I reach into my storage box behind my outfits and pull out a thick, 12 inch, flesh colored dildo out with some lube and climb back into bed and continue watching.
I lay on my side and slide my dildo under my black pantyhose and slide it into all the way into my smooth hole. I squeeze my cheeks curate back and forth as I turn on the vibrate function and begin to immediately shake as I slowly rub my leaking nylon cock while my eyes are fixed on the screen, watching this attractive older man slide is cock in and out of a beautiful crossdresser in white lingerie. The feeling of my hose on my legs and the large vibrating dildo inside of me, begins to send waves down my body and I begin to have a massive prostate orgasm. For a good 2 minutes, I lay on my side shaking and moaning as my cock leaks through my hose into my bedsheets. This drove me to another level. At this point, I need the real thing.
I make my way to my email and **********. I didn’t have a regular bud at this time and have, on occasion, ventured to ********** to see if I can meet anyone. Usually unsuccessful when on there, I didn’t really think I’d meet anybody but you never know. However, as I open my email, first email down was from a friend I had recent met online named Randy. A few weeks earlier, Randy and I met on a men’s web chat site that was popular at the time. He was married and in his mid 40s and like me, he had a pantyhose obsession. We had exchanged pics via email and chatted a dozen or so times and always had a fun time. He is a total top and since I’m a bottom, we were a match made in heaven, online at least. He lived about 30 miles away, so our relationship was strictly online, but we did chat about hopefully some day meeting in person. I was single and had my own apartment, so I could host discreetly if he could ever sneak away. I grow excited as I see his email address in my inbox and open the message.
I see the message was from two hours prior, in which Randy tells me that his wife is away for a week and that he’d love to chat again soon and hopefully meet while she was away. We hadn’t chatted in a week since I was so busy with the party and was happy just to see his email and that he was still interested. I smile and immediately hit reply and tell him what I’m doing and what I’m wearing and tell him he can come over any time he wants. It’s 1am so I’m expected maybe a response tomorrow morning earliest. Luckily, I receive a immediate response. Randy wrote “mmm that sounds so sexy, maybe I can come over now and stay the night?” This response made me shiver in delight. I immediately reply, “Oh yes Randy, I’d love nothing more. Here is my address” Randy replies “Great. I had pantyhose on already so leaving now. I’ll be there in 30 lover”. I reply back to let him know I can’t wait and gave him my apt number and told him my door was unlocked and come right in!!! Xoxo”.
My excitement is through the roof. My buzz wearing off but lust starts to grow. Going off of past chats with Randy, I know he loved layered nylons and fully dressed crossdressers. I go back to my closet and slide a pair of red argyle thigh high stockings over my black pantyhose and grab for my makeup kit and long brown wig and black stilettos heels and head to the bathroom. I excitedly work on my lips and eye lashes quickly and affix my shoulder length black wig. About 20 minutes after I opened Randy’s email, I’m in my wig, makeup, heels, layered nylons, and black leather teddy. Deep down I’m hope he doesn’t flake. We never met in person before but chatted so much that I was really hoping he would arrive. After I look at myself in my bathroom mirror, I head back to my room to get my dildo and laptop and move to my living room. I turn on the light and lay on my couch as I slide my dildo back in me under my black hose and lay on my back as I watch another porn from this same actor, who I’ve grown smitten of. I’m in such lust as I suddenly hear the sound of footsteps. I live in a complex with 8 other one bedrooms and outdoor access to the building. I grow more horny as I hear the steps get closer to my apartment, knowing this is finally happening. I continue playing when I suddenly see my apartment door slowly open and I see a really attractive and fit man enter. I see that Randy is very handsome, has short blonde grey mix of hair and stubble. Randy was wearing a pair of dark jeans and a hooded sweatshirt as walks in and sees me full dressed in layered nylons. Randy smiles widely and begins to undress after he opens the door. Randy tells me “your such a hot fucker, you look so amazing.” I smile up at Randy as I pull my dildo out of my ass and pantyhose and place on the floor before me. I stand up and walk over to Randy and whisper “you are absolutely gorgeous” and we start to make out while I help off his hoodie and tshirt underneath and help him out of his jeans and see Randy’s rock hard 8 inch cut cock in tan pantyhose. Our eyes open as we kiss, my red lips carressing his. So excited that we finally meet in person after so many long and hot chats. We stand and kiss for a few minutes before Randy leads me back to my couch.
Randy lays me on my back as he climbs on top of me. I wrap layered nyloned legs around Randy’s back and squeeze him into me, as we continue making out passionately and grinding our nyloned cocks together. I can feel our cocks leak on one another’s, as Randy grinds up and down my smooth body, with my legs wrapped tightly around him, pulling him into my body. The passion builds every second we kiss and after 5 minutes of this, Randy gets up and smiles at me and says “I’ve thought about you so much, I need to be inside of you”. Randy then leans down and rips a small hole in my seamless black hose and lowers his head down and licks my smooth hole, his tongue entering me and tasting every inch of me. I lean back and rub Randy’s hair as I raise my legs and moan. Feeling his tongue inside of me drives me wild, and I moan louder. Randy gets up and kneels on my couch and rips a hole is his tan pantyhose so he can free his gorgeous 8 inch cut cock. He then gets back on top of me and bends my legs back behind me, as Randy hovers over me and kisses me again. Randy then slides his cock inside of me slowly, as I close my eyes and moan. Laying beneath Randy, I feel so incredibly hot and slutty every second I’m with him. We start to kiss, as I dangle my nyloned legs over Randy’s broad shoulders and he begins to pick up the pace. Our lips and tongues caressing, feeling all of Randy’s large cock. My moans gets louder as Randy begins to fuck me hard on my couch as I lay defensively beneath him. Randy would become more dominant as we continue as I simultaneously grew more submissive, as we could tell from me moaning “fuck me baby”.
Randy looks down and firmly grabs my neck as he pounds be harder and harder. I look up seductively when Randy gets more dominant and encourage him. He starts to slam me hard and calls me by my fem name, Savannah, and starts manhandling me on my couch as I lay dressed and moaning. The feeling of his cock sliding in and out of me, drives me wilder by the second, worshiping Randy more and more. Around twenty minutes after he first entered me, Randy starts to fuck me roughly, as I lay folded under him. My cock continues to leak though my black nylons as he thrust in and out. The sensation is so great that my cock starts to swell under my hose and I begin to shake and shoot a huge load hands free over my black teddy through my black seamless pantyhose. Randy smiles at me, startled as he makes me cum with his beautiful cock and tells me again how hot I am and to get ready for his load. I loudly moan “cum in me Randy, please please” loudly as he thrusts in and out really fasts and moans loud with me. My couch shaking against the apartment wall. Randy then let’s out one last huge moan before he plants his cock deep in me and I feel the warm sensation of his semen filling up inside my hole. I moan and kiss Randy and wrap my legs around him again as he grunts and unleashes his load deep inside of me. We kiss passionately as I hold Randy close to me. He looks at me says “wow”. I look back at Randy and tell him how incredible he is.
Randy then helps me up and we walk hand in hand to my bedroom. I take off my heels and we lay in bed together. I lay my head on Randy’s strong chest, as he rubs my head and we chat. I tell Randy “when I got him from my parents anniversary party, I planned on going right to bed. Two hours later, here we are”. Randy kisses my head and says “I’m so glad I was online when you replied. I wanted this so bad”. Randy then jokes, we were pretty loud, your neighbor might know your secret now.” I turn my head on Randy’s chest and smile “I don’t care, you’re incredible. I’ll do anything for you. Randy joked “we will see”. We chatted and little bit more as I laid in his arms for a little while before falling asleep together at around 3am. Little did I know that the rest of my weekend was about to become the most memorable in my life. To be continued……
11 months ago
