tagTranssexuals & CrossdressersIf I Did It- - -And I Did Ch. 03

If I Did It- - -And I Did Ch. 03


I never called the guy from the bookstore and never went back to that particular store again. I was really conflicted as to my sexuality at the time and what I'd done and how much it thrilled me messed with me a lot! I was dating and fucking girls and after the bookstore episode I was fucking more of them in some need to prove that I wasn't a fag (I've really thought about this over the years).

When I graduated from college I got a job in San Diego. The city was a far cry from Dallas in most every way. Weather, night life, beaches etc. My parents loaned me the money for my first house. I had a great job that paid well. A nice car. Clothes. Things were pretty cool for an attractive (if I do say so myself) looking 24 year old guy! San Diego has to be one of the easiest places to meet girls in the country. I was having a ball with that too. But I craved sex with men like crazy. And I was so reluctant to go after what I wanted.

I was also building up a ladies lingerie wardrobe that would shame most women. My house was a three bedroom. One of the guest bedrooms was my self-sex gratification room. I had a dresser with all of my lingerie in it. I had ten or twelve pairs of hot shoes in the closet. I had make-up (and I was getting good at putting it on) and perfume along with a 32 inch TV, a VCR and lots of porn. Lots of transvestite porn. Lots of gay twink porn. Lots of mmf porn. I had a queen bed with an iron headboard that I could use for nylon cords and a chair that was perfect for laying in with my legs up the back of it and then over my head. I had a collection of dildos ranging from a rigid five inch on up to a long fat nine inch. I had a low little bench that I could put a suction cup dildo on, straddle it and fuck myself silly. I also had a couple of butt plugs that I used to keep myself ready in the event that I got lucky and found a hot guy.

I was dating around with a few girls none of which was serious. There was this one girl named Pam who was a spectacular fuck. She was 5'8" to my 5'9". I weighed (still do) 145 where she was 140. I had (still do) really full nape of the neck length auburn hair where she had short red hair. Where I was somewhat dark complexioned, she was very fair. And of course where I had nothing but a couple of nipples, she had these beautiful little a-cup up-turned breasts capped off with nipples that were even more sensitive than mine. I swear they poked out to close to an inch when she was hot for sex.

We had been going out together for a few months. One night she was over at my house and we had had a really hot sex session. Tequila and pot were involved and apparently I had consumed enough so that I fell asleep immediately after my second cum. I woke up the next morning and Pam was gone. But she'd left me a note saying what a good time she'd had and that she needed to talk to me asap.

The next day we met for lunch. Over coffee she asked me if I had a sister living in San Diego. I told her that I had a sister but she was in Dallas. She looked at me over the rim of her coffee cup.

"Well then who do all those gorgeous shoes and all that hot lingerie in the spare bedroom belong to?"

I know I must have turned fire engine red! "What are you talking about?" I asked.

She laughed at me. "What the fuck do you mean what am I talking about? You know, the spare bedroom? In your house? The one with the TV, VCR, kinky porn tapes? The spare bedroom with the dresser full of panties, bras, slips, hose? The bedroom with the gorgeous silk women's dressing gowns?"

"Oh. That stuff." Was all I could think of to say.

"Yeah, that stuff." She said. "Who does it belong to? You? You like to wear lingerie? You like to play dress up like a girl?"

I had no clue what to say. I was so fucking humiliated and embarrassed I just wanted to get up and run out the door. But instead I bit my lip and looked at her green eyes. "Well, I guess I like the feel of silk and satin against my skin." This was all I could think to say.

"Do you wear this stuff when you jerk off or with other girls? Oh I know you fuck other girls but that's ok." She asked and then before I could answer she said "Of course you do. I bet you get into some hot sex fantasies dressed like a girl dontcha?" I kind of stammered around not admitting but not denying either. "Oh come on Mark. I'm not pissed off or offended. I think it's cute. And some of your stuff is absolutely gorgeous! It's stuff that I'd love to wear!"

"Really? You would?" I said hesitantly.

"Hell yes! Any girl would love to wear the things you have!"

"Well, would you like to wear some of it sometime?" I asked her coyly.

"Yes I would. How about tonight?" She asked.

We made plans for her to come over that night. I went back to my work feeling like I was ready to jump out of my skin I was so excited. I don't know how I got through the next four hours of work without exploding. As soon as I could leave I went home to get ready for the night.

I shaved myself smooth and put on some loose cotton pants with a t-shirt. Pam got there at seven. She looked great in some simple running shorts and an undershirt with no bra that really accented those extended nipples. I offered to make some margaritas but she was so amped with the prospects for what lay ahead that she just wanted a couple of big fat shots of tequila on an empty stomach.

"I'm too excited to sit down and drink!" She said as she made her way to the hot clothes and toys bedroom. "I just want to try on some of your pretty clothes." She paused for a beat. "And I want to see you in them too!"

Pam was obviously on a mission so I contented myself for the moment by sitting down in the legs over the back comfy chair just to watch her. She opened the closet and rummaged for a few moments. She selected a baby blue silk bra, panties and garter belt combination with some light blue hose and some dark blue open toed three inch pumps (my feet are size 9 ½ so they were going to be big on her but this was all for show and tell soooooo). With no preamble whatsoever she stripped off her shorts, top and flip flops and started to put the lingerie on. Pam naked is a lovely site to see and watching her put on my stuff was just hotter than hell! In moments she was standing there admiring herself in the full length mirror while I admired her from behind. Her little bubble butt looked exceptional in my panties and her long for her body legs looked just sensational in the soft blue hose and heels.

"Well what the hell are you doing just sitting there looking at me?" She asked. "I want to see what you look like!"

"Then you have to pick out something for me." I told her. She rummaged for a few moments and picked a pair of black bikini panties with a diaphanous front. She selected a black low cut bra with some charcoal stay up stockings topped off by a short slip and close toed four inch pumps.

"Show me how you look in this Mark. But I want you to do some make-up for me too so go into the bathroom and do it while I play some more."

I went into my bathroom with the outfit and my make-up kit. First I put on some eye liner followed by a black mascara and a light charcoal eye shadow. A tiny bit of color for my cheeks and a blood red lip gloss was about all the make-up I was into at that point. I put on the panties (which accented my semi-hard cock now visible thru the front and tucked to the side), stockings and shoes followed by an a-cup bra that I stuffed with some tissue all topped off by the schoolgirl length slip. I looked at myself in the mirror and liked it!

When I went back into the bedroom Pam was dressed in yellow bra and panties outfits with some cream colored stockings and a pair of gold four inch pumps. She looked at me and her eyes went wide. "Fuck, Jesus you look like a fucking young girl! Model for me." I walked into the room and did a pirouette for her. "Your ass is gorgeous baby!" She said as she lifted the front of the slip. "And your hot looking cock is scrumptious in those panties and slip!" As I stood there she dropped to her knees and mouthed my cock thru the panties causing me to tent obscenely. She only did it for a minute though. "And I love the make-up!" Over the next hour or so we both modeled my outfits. After a couple more tequilas we were running our hands over each other until we were both hot.

"Now I want you to put on a porn tape for me so I can see what you like." She said. "Pick something girly and raunchy for me baby!" I selected a two guys/one TV flick that I'd jerked off to numerous times and popped it in. I fast forwarded past the obligatory set-up scenes and let what I thought was the hottest scene start. She sat on the edge of the bed while I lounged in the chair. The scene progressed to the point where the hot little TV was blowing one guy while the other guy (who had a cock that was at least nine inches) fucked her from behind. Then they switched to where the guy with the big cock was fucking her face while she lay on her back with her legs up and the other guy fucked her hot wet hole. Pam watched with her mouth slightly open. Her breathing was getting shallower as the scene went on. Finally the big cocked guy pulled out of her face and jerked his cock til he shot in her mouth, on her face and in her hair. The guy fucking her pulled out of her ass and jerked off til he came on her cock and balls. By now Pam had her hand inside her panties and was obviously jerking herself. I was rubbing my cock thru the panties I had on and was rock hard and wet.

"Fuck that's hot to watch!" She said. "Makes you hot too doesn't it baby."

"Oh yeah it makes me hot. Crazy hot!" I told her.

"Tell me the truth Mark. Will you?" She asked. I nodded my head that I would. "You wish you were here dontcha? With two guys fucking your holes? You wish you had their cum."

"Oh fuck yes I do Pam. I'd give anything to be her." I said as I released my cock from the confines of the panties. She asked if I dildo'd my ass while I watched the movie. I told her that I did and that I usually started with one of the small ones and graduated up to the biggest one all the time fantasizing that each dildo was a different guy all fucking me one after another. I told her that I sucked the dildos after I took them out of my ass. She asked if I came with a dildo in me and I told her that I usually did. She then asked what I did with the cum. I know I blushed when I told her that I sometimes smeared it on a dildo and then sucked it off.

"You eat your cum just like when I suck your cock and swallow it? I wanna see you do it!" She said as she fingered her pussy hole for me. "But I want to talk to you while you do it so we need a girly name for you." I'd actually never thought of this but just then it seemed like a good idea. I told her to be my guest and pick a name for me. She looked at me for a minute and then said "I think you look like a Marlene. That's it. From now on when you wear girl stuff I'm going to call you Marlene." I was so hot at the thought of a girl name and her being interested in my masturbation techniques that I decided to throw caution out the door and really put on a show for her.

I told her about how I put rope through the headboard and then tied it to my ankles so I could get them over my shoulders and hold them there. She told me that she wanted to see me do it and wanted to "help". (All this time the TV porn flick is going and we're both watching as we talk) I got out my rope and three dildos along with a 36 inch "spreader" that attached to my ankles and spread me wide. At this point I had on a pair of red silk bikini panties with a matching bra, red stay up stockings and red pumps. I lay on my back on the bed and she followed my directions tying my ankles separately and then attaching the spreader. Then tying both ankle lengths to the length that ran through the headboard. She slowly pulled my legs back towards the headboard until my feet were over my shoulders and I was wide open for her pleasure.

"Oh my! This puts you in such a vulnerable position Marlene!" My clit in my panties was rock hard and really straining so she pulled the panties to the side so that I sprang out. "Your ass- - -no, from now on it's your pussy, is so wide open and is just gaping at me. Your cock and balls- -I think I'll call it your clit and balls from now on, are so exposed to my every whim!" And with that she flicked her index finger against one of my balls making me flinch with the pain. "Ooooooh, that hurt didn't it Marlene. Pam's sorry but she couldn't resist!" and then she bent forward and kissed the top of my clit before she gave it a suck and tongue swirl. Then she took the bottle of baby oil gel from the night stand and rubbed some between her hands. She started massaging it into my clit, balls and pussy hole and soon was putting fingers into me. "What a hot fucking cunt you have Marlene. I've got three fingers in you and I bet you could take some more couldn't you you little slut!"

I was in ecstasy with my clit pointing at my face and Pam's fingers dancing in my pussy. "Oh fuck yes! Put some more in my fuck hole you bitch! Then fuck me with your big cock!"

"I want you to start jerking on that hot fat clit of yours Marlene. I want to see you slide your hand all over it while you pinch those pussy boy nipples of yours! Now do it while I stick four fingers in your cunt!" She was fucking her fingers in and out and wiggling them inside of me making me crazy. I was playing with the head of my nasty clit getting so fucking hot. While her fingers were fucking me she took the largest of the dildos with her other hand and pushed it unceremoniously into my mouth. "Now suck my cock you cum whore! Suck it like you love it!" I sucked it but really couldn't do much since she was fucking my mouth with a vengeance. "Fucking little blow job bitch! I bet you're going to cum buckets and when you do I'm going to feed it all to you like the slut cunt you are." She took the big eight inch cock away from my mouth and pulled her fingers out of me. I felt so empty but only for a moment since she took the saliva wet cock and stuck the head at my pussy hole. "I'm going to fuck you baby! Going to fuck you so fucking good!" And with that she pushed the head into me. As much as her fingers and my past playing with toys had gotten me ready for this it was still a shock when the big fat head popped past my pussy hole ring and into me. She didn't waste a moment as the head was followed by the long shaft sliding all the way into me. Pam had positioned herself so that it looked like the big dick was attached to her (I didn't have a strap on at the time) so it was just like being fucked by her own cock.

I had one hard nipple between my fingers and was pinching it hard while I slid my lubed hand up and down the shaft of my hot clit. Her cock was pounding into me and she used her other hand to push my legs further over so that my clit was inches from my mouth. "Cmon you fucking cunt! Shoot that fucking cum for me! I wanna see it blow our of your clit and into your face! Cmon Marlene! Fucking do it!" She had the big dick bottomed into me and was holding it there giving shoves. It was sliding against my sensitive inner clit and I knew through my sex high that I was going to go off in moments. "Cmon bitch! Shoot the cum out your clit so I can see your eat it!" That did it for me and I felt that inexorable feeling as my girl balls tightened and the cum streamed out of me as I cried out! It was an epic gusher as three or four equal blasts of cum hit me in the face and mouth. I didn't swallow it but kept it in my mouth as more came out. She reached for my clit and squeezed it as her hand slid over it getting all the cum out of me that she could. I could feel it on my face and taste it. "Oh you fucking slut! You gave yourself a blow job hand job! What a fucking cunt!" She pulled the big cock out of me and started scooping up the cum and smearing it all over it. She stopped a couple of times to eat some off of her fingers. "Fucking boy pussy juice! Now give me the cum in your mouth bitch!" I pushed the cum out of my mouth with my tongue. She scooped it up with her fingers and spread it over her cock. "Now suck me clean slut." And with that she shoved the cum covered cock back into my face. I licked and sucked my cum off of it. "Don't swallow it Marlene. I want it too!" So I collected my cum in my mouth until she withdrew the cock. She sat back, pulled aside her panties and shoved her cock into her slick wet pussy. She didn't thrust it in and out more than three or four times before she gave a tell tale shudder and came. She fell forward onto me and pressed her lips to mine. I opened my mouth and her tongue joined mine as we played with my cum.

She pulled away from my lips and told me to show her the cum I had left in my mouth. I opened and showed her the cum pooled on my tongue. She opened hers and showed me the cum pooled on hers as well. "Now swallow with me baby." We both swallowed at once. After she untied me we lay there exhausted. "Jesus but that was fucking hot Marlene! Now you have to show me more hot things you can do to yourself

I wondered if I should show her how a hot bitch can fuck herself with her own clit?

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by Anonymous

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by Anonymous04/13/18

Here it is

Put lipstick on a pig. You have a pig . Put lipstick on a man. You have a slut.

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