The Gigolo Chronicles V Cherrie
- 3 years ago
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Shopping For "Her" free porn video
“So” she said “What the heck are you doing in here!”
I took a calculated breath and said “ Well, I will be happy to let you know that I'm shopping for my one month anniversary.”
“Tommy” she exclaimed “ I had no idea you had a girl, I thought your were the token single guy” said with a wink and a sly smile.
“I did too until..uhmm....Tammy came into my life.” I lied with a great sense of conviction. Not only trying to convince her but also myself. “ Yeah I met here on the net, she lived pretty close so we met for dinner one night and now here we are a month later.”
“Well look at you comin' in here, the definition of no mans land, for your new lady friend. Very cool, very cool indeed.”
Now let me take a moment to describe my friend Sydney. She is a beautiful brunette with long flowing locks. She has a cute face with nice full lips. She is rather small breasted being possibly an A cup. But she makes up for it with an ass that would make a black girl envious. Some may not find her attractive but I certainly have and for a long time. An the best part was she didn't have a boyfriend. Well it was the best part until I had ruined it with this Tammy bullshit.
I flew out of my daze when she rocked my system by simply saying “ Hey I'm not busy tonight you guys wanna met for dinner.” There was no way out now so I simply told her “ Meet me at my house at 7:30 and wear something dressy” She departed my presence with a smile and a confirmation of “See you then” I had no idea what to do.
So I went home with my purchase and sat down on the leather couch in my living room to decided what to do. Should I come clean or make up some bullshit story about how Tammy was sick or some other such ilk. Then I made decision I have been loving ever sense I made it. I decided the secret was to no longer be a secret. But first I drew down the blinds in the front room and pulled down my sweatpants to reveal my plain ole' cotton boxer briefs I normally wore. I took them off quickly and put in its place I silky, deep blue, thong which rode up my ass crack so nice. Yes this was a smart decision in deed . You see I am one of those weird guys who like wearing women's underwear or panties if you will. I didn't do it because I was some tranny or I fancied myself a girl or anything of the sort. No what it truly boiled down to was they just felt great to wear. An the way it hugged my cock in just the right ways made it worth the risk and embarrassment. You see normally I would just buy them online, but this time I decided to go out and buy them myself. This defiantly provided an extra thrill to the whole experience, and now I was feeling extra horny. But I decided it probably would be better to get the house for Sydney and I tonight. So I threw on some old clothes and went to work cleaning the house to a level which it hadn't obtained in years. Once it was all complete it was 6 o' clock. So I put on a nice blue and black dress shirt and some dress slacks and waited for her arrival. When I was changing I thought of putting on a more "normal" form of underwear but choose against it for the wonderful silky thong I had been wearing earlier.
I decided I probably should have some dinner made in case she wanted to stay and have dinner (I certainty hoped she would). The whole time I was making the grilled chicken and oven potatoes all I could think of was how wonderful It could be if this little encounter went my way. But on the other hand it could be disastrous and ruin a friendship I've held for ten or so years. I just tried to stay positive and carried on. When I was done with the chicken and with the potatoes in the oven I sat down for a rest. I looked at my phone it was 7:15, she would be here very soon. No sooner had I thought that than came a knock on the door. I opened the portal to reveal one of the most beautiful women I have ever seen. Sydney stood there clad in a little red dress of delight, it hugged her in all the right places. I stammered out " You look absolutely ravishing"
"Well thank you, don't look to bad yourself handsome. So where is she?"
I thought for a moment and replied " Well your a bit early and she is still getting ready. You want anything to drink?" She said she wanted a bottle of water, so I went to retrieve it from the garage. While I was away she took a quick peek around the house and tried to find Tammy. She of course had no luck in finding my ghost girlfriend. So when I walked back in the kitchen she stood there with a "What the fuck is going here" look. I calmly told her to come into the living room and sit down. The cat was walking out of the bag
She sat down on the couch and I sat in a chair across from her. She then started in with " So what's going on Tommy, where's Tammy"
Well I swallowed hard and took a nice sip of air and began " Well Sydney It's time to tell you the truth about Tammy. To be honest there is no Tammy, I made that up." She had a look of surprise and discomfort on her face. " You see the reason why I was buying panties this afternoon was because I wear them." This was the point where either she would accept me and stay for dinner or become disgusted with me, leave, and make me a laughing stock.
"Well that's....uhh....REALLY." I nodded yes and she went on " Tommy that's a bomb you just let off and I'm trying to decided you motives for having me over tonight."
"I had you over to begin with because you asked to have dinner with me and "Tammy" and I didn't want to refuse you. So I agreed knowing full well that this could be disastrous for me and our friendship. But once I thought about it I realized that after harboring this other side of me I decided to let it out for someone. I hope that you understand I'm telling you all this with the hope that you will accept who I am and stay for dinner." She then shocked me by asking a question I hadn't thought of.
"Are you wearing some right now?"
" Uh..yeah I am" I admitted a little ashamed. She then said something that I can never repay her for.
"I think that's really cool, in fact I think it's kinda hot." I was stunned I hoped for a positive response but that was definitely not what I expected. I blushed a little and just said " You wanna have some dinner, we can talk more then." So I got out the potatoes and chicken placed them out at the dinning room table. We sat down and began eating our meals silently, I think it was probably because A. I was processing what she was saying and B. she was doing the same with what I said. Finally I said "so how's work" we then awkwardly chit chatted for about 20 or 30 minutes then something more interesting came up.
"So how long have you been a pantyboy." she said with a smile and a wink. I explained that I had been doing it for about two years and really enjoyed it. She then continued " So what is it about it that you like so much."
"Well you see I was always very turned on by women and their panties, to me it embodies the sexyness and vitality of the female body. Sure it's not actually part of her but it is an extension of her personality. Plus it's so close to her...umm..parts and I find it to be very seductive. Anyway I started to think about it and realized I really hate mens underwear. There dull, kinda ugly, and pretty flavorless. So I did some research and got myself a pair of panties to see if I would like wearing them. I of course have loved it ever sense."
" Yeah I have to admit mens underwear is just plain awful." she agreed " But of course most other men wouldn't have the balls to do what you do. Like I said I think it's pretty hot." From there our conversation veered this way and that way. We eventually ended up on the couch watching a movie and sipping red wine. she then leaned in and laid her head on my shoulder. She snuggled up and got real close and for once I felt like a girl may really like me for me. She then dropped her bomb of the evening " Do you think I could see what you look like with your panties on pantyboy. I'm curious as to how you would look in them." I couldn't deny that devilish look of lust she was giving me.
But first I said to her " Are you sure because the panties are hot, I'm not sure if I look hot with them on." she then stated it was time to find out. she go down on her knee's and began to unbuckle my belt. She took off my dress shoes and pulled down my pants to reveal my lacy blue thong I had been hiding from her all night. She made and "O" with her mouth and I couldn't tell from my position weather that was good or bad. "Stand up, take off your shirt and show me what you got there." So I stood up and took of my shirt and gave her a little show. I swung my hips around and touched my body all over. I think I did a good job because she then stood up without uttering a word and dropped off her dress. She was wearing a matching bra and panty set. It was fire red and absolutely dead sexy. She stepped out her dress and reached behind her back to let loose her small but oh so perky breasts. "Now were both just in our panties. Tommy I have to admit at first I thought you were a little crazy for doing what your doing. But the more I think about how naughty your being and how unbelievable sexy you look in your little blue thong.The more turned on I am and I must say you look sexy as fuck right now." An I could tell she was very turned on by my little number because just then I saw a bead of her sweet nectar sliding down her inner thigh. She then immediately dropped down on her knee's. " Well well our little pantyboy is a boy isn't he mmmm I can see your hard cock through your thong." She then pulled my panties down around my ankles and revealed my hard, throbbing, dick. I am not vastly well endowed by any means but thankfully my 6 inch dick seemed to be just fine to her because she then went straight to work on my pulsation member.
I let out a little moan as she stroked me, sucked me and fondled my balls all at once.She looked up at me with this intense look of "fuck my mouth" of course I was more than happy to oblige her. It was an intense feeling I hadn't felt for too long and speaking of long it wasn't going to take me long to cum at this rate. Up and down, up and down she went. Finally I couldn't handle it anymore I was going to explode. "Syd I'm gonna cum, I'm gonna cum mmmmmm oooohh don't stop please don't stop. I'M CUMMING OOOHHH." I then shot the biggest load I had ever had before. Rope after rope of my thick white goo pour on to her tongue. I came for so long it didn't seem real and then finally it stopped and she pulled my cock out of her mouth to show me all my cum in her suckhole. She winked at me and swallowed it all and smiled up at me. "That was the best blowjob I've ever had, you madam are a fellatio master if I do say so myself." I then got up and told her to lay down on the couch I wanted to return the favor. I got between her legs to feast on her sweet love hole. I started to rub her her through her panties and she wasn't kidding she was sopping wet. Her panties were just drenched with her juice so I leaned in and began licking all over her panty clad pussy. "MMMMMmmm" she moaned and moaned as I licked her panties and her inner thighs. I finally decided it was time to let her have the real thing. so I pulled her panties to her ankles and dipped my two finger into her love tunnel. Now that there were coated I began rubbing on her love button.
"Tommy don't you dare stop doing that MMMMmmm Oh your so good to me mmmm Suck out every drop my dirty whore lick me clean." I was more than willing to oblige her It was near that point I dove my tongue into her pussy hole and I began rubbing on her button with my hand. As she was already so turned on by the time I started licking her it wasn't going to take to long for her to cum. "TOMMY suck my pussy, OH YESSSSS OHH OHHH OHH FUCK MY HOLE WITH YOUR TONGUE. mMMMMMMMmmM I'M GONNA CUM ALL OVER YOU" An sure enough she did do just that, she squirted all over my face. An I mean ejaculation level squirting, so I did the only thing I could think of. I cupped her pussy mound with my mouth and quite literally drank her. When she had stopped twitching from the orgasm she just had she looked up with me big puppy dog eyes and said the hot six words you can think of " PUT YOUR COCK IN MY PUSSY" I did not need told twice,I tossed her panties in a pile next to mine and lead her to the floor and got on top. I rubbed my tip on her hole I slowly entered her. " FUCK.... ME.... HAARD" she said with bated agonized breath. I then started pound her nice and good. She was of course extremely wet already so pretty soon my thighs and everything else was drenched in her girly-juice. I tweaked her pink little nipples and massaged her breasts. I was so turned on at this point and wanted to cum in her but I wanted it to last. So I pushed on in and out for a bit longer till I could take it no longer. This long neglected cock need to cum her pussy.
" Are you on the pill"
An instead of saying yes or no she said something a little more exciting " OH YEAH PANTYBOY FUCK MEEEEE FUCK MEEE HAAARD. PUMP YOUR HOT CUM IN MY CUNNY. PLEASE TOMMY FILL ME UP I NEED YOUR CUUUMMM OOOOOHHH AAAAAAAAHHHHAHAAAHA!"
" I'M CUMMING TOOO AHHHH" an at that exact moment we both came together. My cum pumped into her like a garden hose and she convulsed and bit her lip writhing in orgasmic bliss. Over and over I came inside her again wondering if I ever would stop.
When we had both come down from our highs she looked me right in the eyes and said " That was the hottest fuck I have ever had. I mean I've never even squirted before today. Your the best lover I've ever had."
" Sydney your the most beautiful sexy creature I've ever seen in my whole life and you are the best I've ever had and probably ever will." She then did something rather odd she got up and left the room and went to the kitchen. She came back with a soup spoon and her sexiest voice told me to spoon feed her my cum from her pussy. An that was the moment I realized that she was my cumslut and I her pantyboy. Watching her eat my cum from her pussy like that is easily the hottest thing I've ever seen. I could tell that we were going to be together a very long time. -->
Emely
- 24.08.2021
- 18
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