Jennifer's CumPulsion III: A Trip to Texas
By Jennifer James jennyjamestg@hotmail.com
In the Fall of 2000 I had a single business meeting, on a Wednesday, arranged in Texas's largest metro area. I decided to make a mini vacation out of it, and made arrangements to arrive there the Friday morning before, and to fly back right after the meeting itself. Since I only had the one meeting, I had decided I would spend the entire time, except for the single meeting itself, as a woman. Arriving at the airport, I rented a red Grand Am, and checked into my hotel suite with 2 huge suitcases that contained exactly one business suit, and was otherwise filled with a woman's wardrobe.
I first unpacked and hung up my wardrobe, and laid out all my makeup, and immediately ran a hot bath. I lay back in the tub and leisurely shaved my legs, bikini area, and armpits. I don't really have any other body hair, except for a very fine fuzz on my arms which is unnoticeable.
Then, draining the tub and turning on the shower I gave myself my usual extreme close shave on my face, which is not very hairy to begin with, then washed my hair and began drying off. My skin is naturally very soft, but I used a silky body lotion all over to make sure it stays that way.
I then painted my toenails a dark plum shade, 2 coats, and then put on a shiny topcoat.
Slipping into a red sleep chemise, I plugged in my laptop and got online to check my messages. As usual, I'd put some ads in the Hotmail Classifieds (now defunct), under the 'OTHER' category. And as I always do I'd posted a picture of myself that was not my best, but decent, in a casual summer dress out in the real world.
For the ad itself, I'd listed myself as a 'transgendered girl' visiting town and looking to meet a nice guy for dinner and drinks, and whatever happens afterwards - public dates only, no motel room meets, no obesity, and no crossdressers'.
When I checked my messages, I found I had gotten 6 more since that morning responding to the ad, making a total of about 60 I'd received so far. Now even though the amount of messages was high, I knew that once I started weeding thru them I'd maybe have 15 that I'd bother emailing my hotel phone number to, and out of those that called maybe 3 would turn into actual dates.
So I quickly went thru the new ones, added the possibles to my list, and sent a generic email to 12 guys, using BCC (blind carbon copy) so they wouldn't know it WAS a list, saying I'd like to talk further and included my hotel phone number. I then got off line, it was about 4PM by then, and decided to get ready to go out, with or without a date for that night.
I pulled a chair into the bathroom by the makeup and mirrors, and began to get ready for the night. I started by putting on my foundation, sponging off the excess afterwards, and 'fixed' it with setting powder - and the phone rang.
Answering the phone, I found out it was Tom, a guy I'd written to earlier. He was only in town for the night himself, and told me he was a 58 year old guy, average height and weight, and that he'd love to take me to a nice dinner, my choice of restaurants. He sounded nice so I gave him my address and room number, and told him to pick me up at 6 PM.
I went back to my makeup and put on black liquid eyeliner, top and bottom, eyeshadow in deep pink and smoky blue, black mascara, 2 coats top and bottom, accented my tweezed brows with pencil, brushed rose blush on my cheekbones, and lined my full lips with pencil then put on a light plum lipstick with a brush.
I had just finished with the lipstick when the phone rang again. This time it was a guy named Bill, and after a few minutes I realized that he was just looking for sex and not ready for primetime, so I blew him off.
And before I could get back to getting dressed, the phone rang again and it was Bud, a guy I'd gone out with on previous visits who asked me if I'd like to do something during the day Sunday - so I said it sounded good and I'd call him late morning.
Anyway, I pulled on a pair of lace top nude sheer stockings, a black lace garter belt, and a black lace trimmed bra and panty set. And since I was planning on going to dinner at a Mexican Restaurant called Papacito's, a busy yuppie crowd place, I pulled on a black short (but not micro) skirt and slipped into a white satin blouse.
The hair came next, my light red-brown wig that was just past the shoulders with bangs, and combed back on top. I put on a silver ankle chain, 2 silver bracelets, a silver serpentine necklace, silver pinky rings on each hand, and 2 sets of silver hoops in each pierced ear, 2 1/2" in the front holes, and 1 1/2" in the rear holes. Slipping into a pair of 2 1/2' black dress heels, I then applied 2 coats of plum nail polish to match my toes and lipstick, and a top coat, and was done.
It was now a little after 5:30 so I sat down to relax and let my nails dry.
At 5:55 there was a knock on the door, and I got up and opened it to see a nice looking guy there, slightly shorter than me in heels, with grey hair and a short gray mustache. So I said 'Hi! - just let me grab my coat' and he said 'you look great'. So I grabbed my black leather dress coat, and purse, and we were out the door.
In his rental car, he asked 'where to' and I told him how to get to Papacito's, on Restaurant Row very close by. The place was packed so we parked in the back of the lot, and when we got inside there was a half hour wait so we went into the bar, got a few glasses of wine, and found an uncrowded corner to talk.
It turned out he was originally from the area, but was now living in Japan, and had once had a long term TG lover. He was very nonchalant about being in a crowd like that with me, which was nice.
Now, I'm very comfortable being anywhere as a woman, but a lot of guys aren't - and as much as we all like to think we can pass anywhere, if someone's really looking there are always signs. And, since there aren't that many genetic women out there who are 6' tall with hair and heels, perfectly made up and well dressed, I always get that second glance, which is when people really look closely. But, I have an attitude, and can stare down anyone, and even when I am read people are rarely sure - after all, who expects to see a transgender girl in a place like that looking that comfortable.
We were finally seated, and I ordered a mexican seafood dish and another wine, and we had a nice meal. And after dinner, while we were having coffee, I slipped my shoe off and was running my stockinged foot up and down his leg and ankle, and finally across his groin, which was already hard. Tom paid the check, and we left the restaurant and got in his car. 'Where to?' he said, so I suggested we drive back to my place, and we did.
When we got into my room, I excused myself, and went into the bathroom to get comfortable. I slipped off the blouse and skirt, fixed my makeup, and came out in my bra, panties, garter belt, stockings, and heels. Tom was sitting at my kitchen counter on a high stool, and I came over and gave him a light kiss on the lips. He responded with a little tongue, so we stood there for awhile gently kissing, as I reached down and began lightly rubbing his cock thru his pants. He was already hard, so I suggested he get more comfortable, and we moved over to the couch and I helped him undress. When he finally pulled down his shorts, and his cock popped out, I saw that it was cut, and a nice 7".
I moved in and pressed my body against his, and began to kiss him again, slowly, tongues touching lightly, and reached down and began to slowly stroke him. Then I slowly slid down onto my knees and slipped my warm mouth over his cock, and began to gently suck as I lightly ran my fingertips over his balls. Not wanting it to end too quickly I stood up again, and kissed him, and then led him over to the bed. He laid down, and I laid next to him and kind of fit myself to his body, my leg in between his, and started kissing him again, and we lay there for awhile, petting each other and cuddling as we kissed.
Then I turned around and laid my head on his thigh as I began to lick and kiss his cock, lapping at the head and running my tongue up and down his shaft. I slipped him into my mouth again to get him really wet, then leaned over into his groin and began to lick his balls, as I kept my hand around his shaft, gently kneading his cockhead. I slowly took his testicles into my mouth one at a time, sucking gently, and then moved up and took his cock into my mouth again.
While I was doing this, he had been running his hands up and down my stockinged legs, and over my ass, but avoided touching my cock - which had gotten hard on its own.
I began to gently suck on his cockhead, and then began to move my lips up and down his shaft, wetly, keeping my tongue pressed against his cockshaft. I could feel him start to get tense, and I began to moan quietly, which guys usually love. My lips were going up and down his shaft in a slow rhythm, his cockhead just entering my throat on the downstroke, and all of a sudden he moaned -so I moved my lips back out so just the head was between my lips and sucked and tongued his cockhead, and suddenly he tightened and his cum began to spurt into my mouth, very thick and gooey, and I kept sucking till the last drop was drained. I swallowed it down, but kept his cock in my mouth till it got soft.
And then I slid back against him and cuddled into his body, his soft cock still in my hand. I looked into his eyes, and he just said 'wow!' So I gave him a soft kiss, and lay back down, my head on his shoulder. Somehow, I fell asleep in his arms like that, and eventually woke up with a start. I saw that he was also asleep, on his back, so I gently pulled myself free, and moved over, kneeling between his legs facing him, and he woke up just as my mouth slipped back onto his cock.
He quickly said 'I doubt if I can cum again', and with his cock in my mouth I just said 'mmmmmmmmm' and slowly sucked him back to hardness. I began to gently suck, and very slowly began to move my lips up and down his shaft, and took his cockhead into my throat on the downstroke, and on the upstroke I was using both hands to stroke his shaft at the same time. I was looking up at him at the same time, and kept working, very slowly, on his cock. He began to almost vibrate, maintaining eye contact with me as my lips and tongue caressed his cock, and then he suddenly said 'Oh, Geez' as he again unloaded into my waiting mouth, and again I drained him, and held his cum in my mouth till he was completely done. Finally, still looking him in the eyes, I opened my mouth to show him my cum covered tongue, and then swallowed it down.
He really did look drained, and when he looked at the clock and saw that it was after midnite, he sat up, gave me a kiss, and said he had to leave. So he got dressed as I lay there on the bed watching, and when he'd finished buttoning up I got up, and walked him to the door where I gave him a nice lingering kiss. He said he'd had one of the best times ever, and was sorry he was leaving in the morning. So, with a final kiss, I let him out, and went back to the bed where I fell right asleep, with my makeup still on, and the taste of cum still in my mouth.
Saturday morning I woke up and started coffee (the complimentary crap they give you), and hopped right in the shower, avoiding the mirror. I let the water run really hot, and close shaved again, very carefully, as I'd be close shaving a lot this week.
I had a bunch of shopping to get out of the way, so I poured myself a coffee and started on the makeup for the day. Since it was a sunny day, I kept the foundation as light as I possibly could, and all the other makeup also, and used a pale violet shadow with slightly darker highlight, and a deep pink lipstick. Finishing the coffee, I slipped into a pair of tight girls jeans and a V neck girls T, and black low heeled mules. Slipping on my daytime hair, darker and much shorter, and grabbing my purse and short black leather jacket, I headed out to the car.
I drove over to the supermarket and filled the cart with the necessities for the week, coffee, milk, sugar, juices and soda, bread, cold cuts, etc. Getting a few glances, but no comments, I checked out at the register and put everything in the trunk. Then I drove over to Walgreens to pick up a few makeup things I'd forgotten, and some miscellaneous stuff, and paid and left, and finally, since it was almost noon, I stopped in a Taco Bell and had a couple of bean burrito's for lunch, and got a dozen more to go. And then headed back to the room, where I unpacked and organized everything.
I logged onto the internet to check mail, found a few more likely prospects, and emailed them the phone number. And while I was checking my mail the message light came on the phone, and when I got off there had been 2 messages, both saying they'd call back. I spent the next few hours hanging around and ironing, with the TV on in the background, and the phone rang intermittently throughout the afternoon. No dates for that evening, but a definite for Sunday and Monday nights, and 3 other possible's for weeknights to be determined. By 5PM, I was starting to get a little hungry, so I went to do a major makeup fix, took off the foundation below my eyes, shaved again (probably didn't have to, but.....), reapplied foundation, blush, lipstick (fuschia) and darkened the shadow and liner. I put on stockings and garter, a very small tight black tube dress, and open toed black slides. My evening hair went back on, I grabbed my purse, and was out of there.
I headed down to the gay section of town for dinner, and went to a really nice restaurant where I know the owner, and sat at the bar and ordered a drink. As he usually does, the owner came out and joined me at the bar for his dinner, and we ate together companionably and chatted about what had been going on in our lives since my last trip out.
After dinner I headed a few doors down and stopped in The Studio, a fairly sleazy bar where the off duty TG hookers and drag queens hang out, just to say Hi to a few people I'd probably know there. The bar had a really cute bartender, very young, and about 6' with short brown hair, brown eyes, and a great body. We were both flirting a little, and I found out he was 19, straight, and his uncle owned the bar. But he was on duty all night, so at a little before 9PM I took off and headed over to my favorite bar, a place called Spanky's.
Spanky's is basically a straight bar, but is also the meeting spot for BBW's (extremely fat chicks in suggestive clothing) and their admirers, who are invariably skinny black men. The rest of the clientele are mostly couples looking to swing, bisexual women, and anyone in the neighborhood - and everybody there is at the least, liberal minded. The place was already packed when I walked in, and I got a seat at the bar and looked around. Right away there was a cute guy a few stools down staring in my direction - and a few minutes later I looked up to see him next to me. We flirted a little, and I said 'feel like fooling around at all?' and he said 'I have a place around the corner', so I grabbed my purse, we got hand stamped at the door, and went out to his car.
A few blocks away he pulled into a garden apartment complex, and we parked in front of his door. But when we walked inside, the place looked like it had been ransacked! The smell of mildew was pervasive, there was junk all over, and I immediately stepped back out and said 'I'm sorry, I'm uncomfortable even sitting down in your place' Well, he apologized for the mess, said he'd had a room mate leave and trash the place the week before, etc., but I said 'please, I have to leave', and we walked back to his car.
Well, he himself was somehow showered looking and clean, and certainly cute enough, so sitting there in his car I reached over and began to rub his cock, which felt above average in size. He went to kiss me, but I didn't want to mess up my lipstick in the car and told him so, and instead I loosened his pants and pulled down his shorts, and his cock sprang free - It was about 6" long and wider than average, and I leaned over and took him in my mouth, and began to suck him off in the parking lot. There were no sidewalks, so very little foot traffic, and he leaned his seat back and relaxed. Bobbing my head up and down on his shaft with a lot of suction, and fondling his balls, I quickly had him on the edge, and he suddenly reached down and grabbed my head and thrust into my throat, shooting his load with the thrust and holding my head in place as he flooded my esophagus with his cum, which I couldn't even taste till he pulled back his cock, and then the cum began dripping back out of my throat and onto my tongue where I could taste it.
I don't generally like being mouth fucked, but for some reason I don't mind at all when it's only the 'cum thrust' that goes forcefully into my throat, and for some reason instead of gagging, the feeling of the cum directly flooding my throat makes me really horny, and if I want I can sometimes cum myself without even touching my own cock - but I held back, and drained the last drops, keeping him in my mouth till he started getting soft. Then I sat up and fixed my lipstick in the passenger side mirror, as he started the car and drove off without a word. Back at Spanky's, he pulled up to the door and said 'I guess I'll take off, that was great though. I'd like to suck your cock the next time' 'Sure' I said 'the next time' (yeah, right) and I got out of his car and went back into Spanky's.
Once inside, I realized I really had to pee, so I got in that interminable line for the unisex bathroom at the back bar. I found myself in line behind a cute black guy, and he started telling me how great I looked - with the usual sincerity. Then he asked me if I liked black cock, and when I replied 'sometimes' he took my hand and slipped it inside his waistband, and there was a very large cock in there.
So when we finally got to the bathroom door, we both slipped inside, and I immediately sat down to pee, and while I was peeing he stood in front of me and pulled out his cock and I took him in my mouth. Well, partly, anyway, he must've been 10 inches long! I was just licking and sucking on his cockhead as I peed, but as soon as I was done, I tucked myself in and squatted in front of him and got serious. The usual knocks on the door from the next people in line had already started, so I began to forcefully suck the end of his cock while I stroked him with my right hand, and I quickly got a rhythm going and he soon began to unload onto my tongue as I jerked him off into my mouth, and he continued to feed me his sticky load. By the time he was done, the knocks on the door were getting very loud, so I stood up, quickly fixed my lipstick, said goodbye, and walked out of the bathroom to a few dirty looks.
Back at the bar, I ordered another wine and relaxed a little bit, talking to the bartender, when I saw Darren come into the bar area. Darren was a cute, sweet guy that I knew from past trips, and the kind of guy you want to cuddle. He saw me, a big smlie came onto his face, and he came over and gave me a big hug. 'The girlfriend away this weekend?' I said with a grin, and he said 'You bet! How've you been?' So we caught up on past stuff, and after awhile I said 'you feel like coming back with me for the night?, and he said 'Sure, love to' So I gave him my address, and told him I'd meet him there - we walked out together, and I headed back to my suite.
I got comfortable, put on my red chemise, changed into my most comfortable hair (since I'd be sleeping in it), fixed my makeup, and was just pouring myself a glass of wine when there was a knock on the door. I let Darren in, poured him a glass of wine, and we headed right over to the bed, where he got naked, and I got naked under the chemise.
Darren is an admitted bisexual who also has a thing for at least this T girl - We started in with slow kissing, and began slowly fondling each others cocks. Normally I'm not crazy about having mine played with, but with the right guy it's different. So I slid down into 69 position and took his cock in my mouth, and began to gently lick and suck, and I soon found his hot mouth wrap itself around mine also. We sucked each other for a while, very slow and gentle, and then went back to kissing and petting. He was a good kisser, gentle, just enough tongue to tease, and we slowly fondled each other's bodies, and then I slipped back down and took him back in my mouth.
As he began sucking on me, I took his cock inside my mouth and licked and sucked gently on his cock head, moving my lips in and out, but just over the first few inches at first. Gradually I deepened my oral strokes, still going very slow, and went right down to his pubic hair on the downstrokes, with his cock going an inch or 2 into my throat, and then out to the very tip on my upstrokes. I very gradually quickened the rhythm and suction and increased the pressure of my tongue along his shaft, and he was now moaning and sucking like crazy on me, and suddenly he began shuddering and released his load of hot cum into my mouth. As his cum started flowing I kept just the head of his cock between my lips. He was still sucking wetly on me, and when the the taste of his spunk flooded my mouth, I let myself go and began to cum into his mouth. We lay there draining each other's last drops till we were both soft.
Finally, I turned around and entwined myself in him as we lay side by side on the bed, and I fell asleep with my hand around his soft cock.
A few hours later I woke up, with his cock still in my hand, and slowly disengaging myself I got up and kneeled next to him on the bed and gently took his soft cock in my mouth and began to suck it very softly. He woke up just as he started to get hard again, and said 'Oh, baby, that feels great, and lay back with his hands behind his head as I very slowly, and softly, nursed on his cock. Using just my mouth I licked and sucked at his now hard cock, and within a few minutes he said 'Geez, here it cums' and again unloaded his cum into my mouth, as I gently sucked the last drop out.
Then I moved up beside him again, gave him a kiss, and rolled over on my side and fell asleep again, the taste of cum leading me into my dreams.
The next morning we both woke up late, and as I had a daytime date we didn't have time to play again. So I made coffee for the 2 of us, and he left shortly after. His girlfriend was expected back that day, so we said goodbye till the next time.
There was a message on the phone (I hadn't checked the night before), and it was Jon, confirming for that evening. I got online to check email, sent the phone number out to a few more guys (I still had a few open nights), begged off on a couple of others that had been tentative and I'd thought twice about.
I removed my nail polish, fingers and toes, and took a shower and shaved, again avoiding looking closely at the mirror. After drying off I began putting on my makeup, for daytime. I did my toenails first, a frosty light fuschia shade, and I stuck to light purply eyeshadow and a purply pink lipstick, and the phone rang in the middle of my routine.
The guy's name was Jim, and when I asked him what he liked, he immediately said 'I consider myself straight, I like women in relationships, but I love sucking men off whenever I can' He didn't sound like a great prospect, but he was likeable somehow, and said 'I never have anyone to talk to about this stuff, and would love to buy you a nice dinner anyway.' So I agreed, and we set a date for Monday night.
I then finished my makeup, and since it was Sunday and the after church crowd (this is Texas) would be out, I put on white satin bra and panties, white sheer lace top thigh-highs, and a short sleeve flowered dress that would've fit right in at any pew. Not having my white shoes with me, I slipped into a pair of medium heeled black slides, and pulled on my ash blonde hair. I went with gold jewelry and put 1" rings in the front holes and 1 1/2" dangles in the rear holes, a simple gold chain, 2 thin gold bracelets, a gold ankle chain, and a gold amethyst ring. And finally I painted my fingernails, same color as my toenails, and sat back to wait for Bud to show up.
Bud to the door at 1PM exactly, as he'd said he would, and it was nice to see him. Bud is a guy I'd known for quite awhile before we had ever played around. He was the owner of a straight club I used to go to, and I used to tease him a lot, but always took him for totally straight. So, it was a surprise when he finally asked me out on a previous trip. He's a nice looking guy, above average height, with a long mustache and blond hair, and a cock that also above average in size, maybe 8" with a very large head.
I grabbed my purse and a lavender sweater, and we were off. He told me that they had a great brunch at a brew pub over on restaurant row, so we headed there. We both ordered local ales, and went for the brunch buffet. We got some food, starting at the omelet station, and caught up on things. After 3 trips to the buffet, and a second ale, we decided to head back to my place.
Once inside, I slipped out of my dress, and we slowly kissed, standing right by the door. And as we were kissing I undid his slacks and dropped them, and slipped his cock out of his jockeys and began rubbing him gently to hardness. I slipped onto my knees and began to lick and gently suckle his cock, and then he decided to get comfortable, and undressed.
I love being on my knees if there's a decent place to kneel, so I asked him to sit back in the easy chair, and I got between his legs and began to move my lips slowly up and down his already hard shaft, using a lot of tongue, licking at his piss slit, and curling it around his shaft. After he was completely wet, I took him in my hand and began rubbing just the head and lifted his cock up and began to work on his balls.
He was sighing, telling me how great it felt, and I was telling him how much I liked it also, making lots of slurping noises, etc. And in between licks I told him that when he finally came, I wanted him to tell me he was cumming, and then to thrust his cockhead as deep as he could into my throat and shoot his load there (I did enjoy that the previous night!)
He was getting turned on by hearing that, so I took him back in my mouth, and I kneeled up high and bent over his cock, getting a good angle, and began to slowly deep throat him with my tongue pressed against the underside of his cock. and within a a few minutes he said 'I'm cumming!' and placed both hands on my head, holding it in place, as he pushed his cock about 3" into my throat and held it there, and I could feel the blast of cum hit my esophagus as he filled my throat with his juices. When I finally lifted my head so my lips were just circling his cockhead, because of the angle all the cum started dripping back out of my throat into my mouth by gravity. It was a weird feeling, he had left such a large thick load in my throat that when it started back into my mouth and I could begin to taste it, it was almost like my own throat was cumming into my mouth - very cool!
After I let all the cum drip back down, and swished it around in my mouth before swallowing it, I was in for a surprise. Bud, who was a complete virgin in this area, asked if he could suck me off. He'd never sucked a cock before, but had been thinking about it recently and really wanted to. I'm not really much into that, but since he was a virgin :-)
I sat back in the easy chair and he kneeled between my legs, and he got his first taste of cock. He was really getting into it, but had zero technique, and I was having a hard time staying hard. So I asked him if he really wanted me to cum in his mouth, and when he said 'definitely' I had him lay on his side on the bed, and I kneeled in front of his mouth, so I could fuck his lips gently as I watched, and it's one of the positions I can usually get myself to cum in.
I told him to just lay still, and to keep his tongue pressed against my cock and apply a little suction, and I began to slowly fuck his lips, and knew he was loving the feeling of my cock sliding in and out of his mouth. Keeping my own rhythm it didn't take long, and instead of telling him, I surprised him by erupting into his mouth without warning. And I know it caught him by surprise because he choked and coughed and some of my cum came dripping out of his nostrils - which looked really cool!
Anyway, he sniffed back my cum in his nose, and was loving the taste, and audibly slurped it down as he swallowed. I lay down next to him, and gave him a large wet kiss, tasting my own cum, and we laid there entwined for awhile. Finally, though we both got up and I made a pot of coffee - and after the coffee, he took off, saying he'd call before I left.
It was now a little after 4, and my dinner date, Jon, wasn't due till 7, so I took a short nap. About an hour later I got up, had some coffee, and got ready for the evening. I was going to be dining at the Olive Garden, so I kept somewhat subdued in a black wool dress with sleeves, and medium heeled black pumps, but I wore black lace bra, a black lace thong, and garter belt with sheer stockings underneath. I started over with the makeup, but kept the same shadow and lipstick colors as that morning since they went well with the nail polish, and decided to be blonde.
At a few minutes before 7 I answered the knock on the door, and was very pleasantly surprised. Jon turned out to be this really gorgeous guy, late 20's, about 5'10 and slender, with longish dark blonde hair and blue eyes. He had told me in emails that he'd never been with a T girl before, and had stumbled on my ad accidentally - but he seemed very comfortable with me, and we left for the restaurant.
The Olive Garden, also in the Restaurant Row area, was fairly packed, but we got a table right away. And during the meal (penne arrabiata for me) I had a hard time keeping my eyes off him, he was absolutely beautiful. Originally I had planned on taking him somewhere after dinner, maybe Spanky's for a few games of pool, but after meeting him I was dying to get him into bed. So I suggested we go back to my place to relax, and he agreed with a big smile.
Once back in my room, I excused myself and went into the bathroom to slip out of my dress and touch up my makeup, and came back out in bra, panties, and garter belt, and had slipped into some stiletto heels. His eyes lit right up, and he said 'you couldn't have worn anything better, I love garter belts and lace' I poured us a couple of glasses of wine, and we sat on the couch side by side.
As we were chatting I began to lightly touch him, petting his forearm, then his thigh, and I saw that he was getting hard inside his slacks. I leaned over and gave him a light kiss, and when I did his lips parted and our tongues met, and for awhile we just gently kissed. I suggested he get comfortable, and he stood up and I helped him unbutton and unzip - and when nude he looked even better.
His cock was a perfect 8", cut, and the right width for anything. I put my arms around his neck and pressed against him as we kissed, and then I slowly slid down him, my tongue flicking at his nipples, down his flat stomach, and once on my knees I began to lick his cock. I ran my tongue up and down his shaft and across his testicles, and then took him into my mouth, and gently sucked him for a minute or 2.
This guy really turned me on, and though it almost never happens, I was dying to have him fuck me! I asked him if he'd like that, and he said he'd love to, so I went to my night stand and got out a condom, the first time I'd opened one in ages, and a small tube of lube.
I sat on the edge of the bed, in front of him, and again took him into my mouth, slowly moving up and down his shaft, till he was hard as a rock. And then I rolled the condom over his cock, and squeezed some lube over it, and then squeezed some more lube onto my fingertips, pushed my thong aside and rubbed it into my ass, pushing most of it inside me.
I lay on my back on the bed, with my feet still on the floor, and then lifted my legs high in the air. He took a step forward, pushed my thong strap to the side, and pushed his cockhead against my opening as I rested my ankles on his shoulders. I reached down to help ease him inside of me, but I hadn't had anything up my ass in a long time (and only a few times at that) and when his cock finally popped in, the pain was intense and I had to stifle a scream. But he saw the pain in my eyes, and waited a second for me to adjust - and then very slowly began pushing his cock inside me till all 8 inches were buried in my ass.
We were face to face as he began slowly fucking my ass, and it was now feeling great. My cock was still inside my thong, but was getting hard as a rock as his cock was slowly thrust in and out of my opening. With my ankles still on his shoulders he thrust in and out of me, and his strokes were rubbing against something inside me that was causing me to melt, and I was moaning like crazy.
I lifted my legs off his shoulders, but kept them pulled back, and he leaned forward as I reached up and put my arms around his neck, and we began to kiss, gently at first, but as his cock started to fuck my ass faster, our tongues were going crazy against each other. He began to thrust really hard and fast into me, I started a quiet scream, and then he said 'I'm cumming' and slammed his cock as far into my ass as he could and held it there, and I could feel the pressure inside my ass as he shot his load of cum into the condom inside of me.
We both stayed that way, exhausted for a moment, but he quickly started getting soft, and I reached down to ease him out of me, and he stepped back. I sat up and saw that the end of the condom was absolutely full of cum, so I carefully slipped it off his cock and held it carefully as I took his cum covered cock inside my mouth and cleaned it off completely with my tongue and gentle suction. He seemed to be hypnotized watching me do this, I don't suppose many women had ever done that to him. Then, looking up into his eyes, I took the full condom and carefully emptied it into my open mouth, squeezing out the last drop of his cum onto my tongue, and swallowed it down with a large gulp.
I slid up the bed to the pillow to catch my breath, and he came around the bed and lay down beside me. After a few seconds he said 'that was really amazing - a few days ago I'd never have imagined even being here, but that was as intense as any sex I've ever had' So I smiled and said 'well, it's not over yet', and he mock groaned and said 'have mercy!'
We lay there companionably for a while, my head on his chest, and I gently played with his soft cock. I gave him a kiss on the lips and slid down him so me head was on his abdomen and took his shriveled cock between my lips and just kind of licked it softly and gently, and ran my fingers lightly over his testicles. Of course, it wasn't long before he started getting hard again (he was only in his twenties), but I stayed gentle, sucking him very slow and softly, using a lot of tongue and saliva, and soon he was rock hard again.
'Would you fuck me again?' I asked, and he said 'I'll give it a try, anyway' so I got another condom out, and leaning over him I got him wet with saliva and slipped it on him. But this time I got up on my knees, facing the foot of the bed, and presented my already lubricated ass to him. He got up on his knees behind me, and slipped his cock right inside me this time. He began to slowly fuck me from behind as I leaned forward on my elbows, and there was absolutely nothing but pleasure this time around.
His cock felt great as it slid in and out of me, and again I got hard as a rock. He grabbed me by my hips and began to pound my ass, and we bounced against each other, but before he came again I slid forward and came off his cock. I turned around and gently pushed him back against the pillow, and I kneeled between his legs, slipped off the condom, and leaned forward taking his cock inside my mouth.
I got a suction going, and keeping my tongue pressed against the underside of his shaft, I began bobbing my head up and down, slowly at first, taking his cock into my throat at the downstroke and sliding back up to the head. He began to thrust up from his sitting position, and I matched his thrusts with my lips, and we soon were at the same rhythm he'd been fucking my ass with. I knew he was getting close again, and suddenly he grabbed my head with both hands and held it as he thrust into my throat and held it there as he exploded, and my throat started filling with his cum. As soon as he loosened his grip from my head, I slurped the cum into my throat, swallowing as I was still draining his last few drops, and finally I let it slip from my lips as it quickly got soft again.
He really did look exhausted this time, so I snuggled into him, my head on his chest, and he fell right asleep. About a half hour later he woke up, said he had to leave, so he dressed and I let him out with a kiss. He really was a gorgeous guy, and I hoped I'd run into him again sometime, though unlikely.
The next morning, Monday, I woke up late, and decided to laze all day - I wasn't in the mood to get ready for any daytime stuff, so I just lounged around all day, watched TV, napped, ate, and checked email. There weren't any real prospects that sounded great to me, so I didn't bother answering any - and I only had one night left after that one so it didn't matter to me.
Late afternoon I took a long hot bath, and as it's always happened, the ass fucking I'd had the night before had caused some minor intestinal weirdness, so the bath was naturally carbonated :-)
My legs still looked OK, but I shaved them again anyway, and while I rinsed under the showerhead, I gave myself a really close face shave. Coming out of the shower, I dried myself off, and body lotioned, and since my nails still looked really good I didn't have to do anything with them.
Jim, the 'straight cock-sucking guy' I was having dinner with tonight was coming at 6:30, so I had plenty of time, and I sat down and leisurely made up. I used violet/smoky blue shadow colors, and decided to go with a muted fuschia lipstick. I went with white bra/panties/garter belt, sheer nude stockings, and deciding to overdress a little, slipped into a black velvet spaghetti strap dress, with matching shrug. For jewelry I went with silver, a herringbone necklace with 2 matching bracelets, and long dangling silver earrings that almost came to my shoulders, with large CZ studs behind them and a silver CZ solitaire ring. Black shoes and purse, and my blonde wig, and I was set.
Jim showed up a little early, and turned out to be a very good looking, but weathered guy, wearing a business suit, so I wasn't as overdressed as I'd expected to be. He had a nice smile, and asked if I felt like going to Pappadeux, a nice upscale cajun seafood restaurant downtown. We got in his car, a silver Lexus, and began to drive downtown. He was very comfortable to talk to, and we chatted about everything from TG to cock sucking (he really wasn't very familiar with transgender, but was very familiar with cocksucking)
At the restaurant, we were escorted to a table in the center of the room, and definitely caused a stir walking in. But we both acted like we owned the place, and a very friendly waiter took our order (I had blackened mahi-mahi with a creole cream sauce).
Over dinner he told me about a bookstore that he frequents, and again commented on how he really did consider himself straight, despite loving cock - he just didn't care much for the men they were attached to. Well, the bookstore sounded interesting, and since Jim had told me he frequently spent entire evenings there sucking dozens of guys, there was no way I was going to suck his cock - so we decided to head there afterwards.
After dinner was over he drove to this place not too far away, my first ever bookstore experience. The place was huge, and packed, and I was getting a lot of looks as we walked in together. It appeared at first glance that just about all the guys there were black, which turned out to be true, and Jim and I found an empty room and went in, leaving the door slightly ajar
The room was spotless, a side table held a box of Kleenex, and there was a vinyl couch in front of the fairly large video screen. Jim fed a $10 bill into the slot, got a nice hetero cocksucking video going, and the door opened.
A medium sized black guy walked in, and Jim beckoned him over. The guy came over and immediately dropped his pants, and Jim fell to his knees and began sucking the guy off. After a few minutes I went over and squatted down next to Jim, and said 'my turn' and he slipped his mouth off the guys cock, and I had the cock in my mouth within a second. I sucked him for awhile, and had let Jim back to his turn when the door opened again, and another black guy walked in.
I motioned him in, and he came over and stood beside the first guy and dropped his drawers, and I soon had my lips around his rather large 9" cock. Jim and I were side by side, sucking like it was a competition, and his guy started to cum first. As Jim was slurping down his load of cum, the guy I was sucking suddenly grabbed my head and began unloading himself onto my tongue, and I began slurping cum myself.
I had sucked quite a few cocks over the years, but this was a first for me, and looking up as the guy I'd just serviced moved away I saw that the room was almost full - and entirely black. Jim was still on his knees, and already on his second cock, and I sat on the couch and motioned the next guy over. This guy was maybe 7" and not too wide, and I opened my mouth to take him in. Probably because this was a guy to guy place, he began to immediately fuck my mouth, and I basically just kept my head in one spot, and kept up tongue pressure against his shaft, as his cock came in and out of my lips, and very quickly there was another load of cum filling my mouth.
He zipped up, but while I was still swallowing the last guy's goo, I held up my hand to the guys in line, and sat back on the couch to take a break. Jim was already on his third cock, and I sat there for awhile watching him. The guy was unbelievable, he just stayed on his knees as one black guy after another stuck a cock in his face, and in the next half hour or so, he took another 6 loads of cum.
I was starting to get bored when a young hispanic guy walked in and sat down on the couch next to me. He said Hi! and we started chatting, and next thing I knew we were kissing on the couch, in the middle of this crowd of black men waiting to be sucked. I rubbed his cock thru his pants, and he reached up under my dress to rub mine, and I soon had his pants down. I leaned over into his lap and took him in my mouth, and started to give him a very slow blowjob.
He was leaning back on the couch as my lips slowly moved up and down his shaft, and I was getting horny as hell sucking cock in the middle of a room full of guys lined up to get sucked off themselves by Jim. I began sucking harder and faster, and as I heard the guy behind me groan as he unloaded into Jims mouth, I felt the hispanic guy's cock tighten against my lips and he spurted a huge blast of cum into my throat, then a few smaller ones, and I kept sucking till he was drained.
When he finally started getting soft, I sat up, and he gave me a light kiss and left. Well, I was about done, it wasn't really my kind of crowd, but Jim was still lining them up, and I watched him suck off 3 more large black cocks before I asked him if he was almost ready. Jim looked up in a daze, his eyes unfocused for a minute, but then he smiled and said 'sure, hon'
We both straightened ourselves out as the crowd dissipated, and I asked him how many cocks he'd sucked in the time we were there. '14' he said 'about an average night'
We left the bookstore, and he drove me back to my place. At my place, he said he had to get up early (fine by me, no personal interest), but he said he'd enjoyed the company and would like to take me to dinner again sometime if I was ever back in town. And I thanked him for dinner, gave him a kiss on the cheek, and got out and went inside. I was washed up and asleep within 20 minutes.
Tuesday morning I woke up fairly early, and since it was my last full day in town, I decided to go out and do something. So I got up, showered and shaved, put on my daytime makeup, a silver necklace and hoop earrings, and put on a pair of faded girls jeans and a purple V neck T shirt, and slipped into a pair of low heeled black mules and medium short light brown hair.
I headed over to IHOP for breakfast, and read the paper at the table. And after breakfast I headed over to the Galleria Mall for something to do. I basically just window shopped for awhile, but picked up some lace top garter stockings in VS, and afterwards stopped in a Bennigan's, and had a sandwich and a glass of wine at the bar. There was a thirtyish, teary eyed woman a few stools over, and when I asked her what was wrong, she poured out her life story to me. After some hand patting, and words of sympathy and encouragement, I disengaged myself and headed out and back to my place.
One final check of the answering machine, a few messages but no one who really interested me, and I washed my face and took a short nap.
This was my last night in town, and tomorrow was my business meeting at 9AM, with a flight back home at 1PM. I had plans to go out for dinner alone at my favorite restaurant in the gay section, stop by the Studio for a last drink, and then to Spanky's for a last drink. Being a Tuesday night I wasn't expecting much to be going on.
Late afternoon I took a shower, shaved again, and put on my makeup. My nails were still good, and I went with a dramatic look on the eyes, black liquid liner top and bottom, dark pink/smoky blue shadow, and a fuschia lipstick. I slipped into a black thong, black strapless bra, and black garter belt with black sheer lace tops (new from VS). And then I put on a very short black satin mini skirt with a slit in the front halfway up to the waist, a shiny gold tube top, and black stiletto heeled dress sandals. For jewelry I wore very large gold hoops with shoulder length dangles in the back holes, a lacy gold chain, gold rope ankle bracelet, 2 gold link bracelets, and a gold band with small diamonds on my left ring finger. I finished off with my pale blonde hair.
I left at a little after 6, and drove over to the restaurant and valet parked. I sat at the bar, had a drink and chatted with the bartender (a very cute - and very straight - hispanic guy), and was just ready to order dinner when the owner came out to join me. We had a nice dinner together (tilapia with mango salsa), and afterwards I said my goodbyes and left the restaurant.
Leaving my car parked there, I walked over to the Studio a few doors down, and walked into the bar. I had a seat, and the cute, straight, 19 year old bartender walked over, and told me I looked great. I kidded him a little about really appreciating the compliment from someone who could be my son, and we both laughed. He went to make a few drinks down the bar and I said Hi to a few drag queens I knew, and a hooker who was a regular there when not working.
While I was sitting at the bar, though, the bartender kept coming back to me at every opportunity. Curious, I asked him exactly how straight he was, and he said 'well, I've always had a thing for girls like you' and smiled. A little while later he surprised me by taking a seat next to me on my side of the bar, and told me his shift was over. Now, I rarely take 19 year old guys seriously (or even have the opportunity to), but this guy was really a beautiful boy - and could carry a conversation. So when he asked me what I was doing that night, I replied without thinking 'heading back to my place soon, want to come along?' He replied, dead serious 'I'd like to, but I don't have a car or even a license yet' 'I'll give you a ride back later tonight' I said. And then, dead serious again, he replied 'well, I don't have an apartment, I'm staying with friends - and they won't let me in after 11PM'
Honestly, I don't especially like having guys spend the night, mornings can be awkward, and the next morning I had an early meeting in guy mode so morning would definitely be awkward - and I told him that. 'I'm OK with that, honestly, I'm under no illusions'.
Against my better judgement I said 'OK, sweetie, are you ready?', and when he nodded I picked up my purse and we headed out. I had the valet bring my car around, and we got in and drove over to my place.
Once inside, I poured a couple of glasses of wine (though he wasn't yet drinking age in Texas .... but close), and went in the bathroom and changed into a gold satin chemise. We sat on the couch, sipping wine, and I leaned over to give him a kiss. Well, he immediately shoved is tongue in my mouth and pressed his lips against mine hard. So I backed up and said 'sweetie, I'm going to give you kissing lessons' He got a little defensive and said 'I know how to kiss' But I just said 'the girls like it better this way let me show you'
I told him to keep his lips soft and his mouth opened just a little, and I lightly kissed his lips, and then started giving him these light butterfly kisses, and just barely put the tip of my tongue between his lips. Then I told him to do what I did, and we very slowly began to lightly kiss, I gently nibbled on his lower lip, and our tongues were flicking against each other's lightly.
We were both starting to breathe heavy, but I went out of my way not to touch his cock - yet. I stopped to take a sip of wine, and let him catch his breath. And then started in with the kissing again, light kisses, tongues touching, nibbling. 'Isn't this much better?' I asked him, and he replied 'you are driving me crazy! - with a smile. I kept kissing him, but slipped my hand into his lap and began softly petting his cock, as my tongue was slowly slipping into his mouth. He made a small groaning sound, and I stopped and said 'let's get comfortable'.
We stood up and I undressed him completely and slipped out of my heels and chemise, and then I threw my arms lightly around his neck, and stood on my toes as we continued to kiss. I reached down and took his cock, which was a perfect 7" and tapered, in my hand as we kissed, and almost immediately I felt some pre-cum dripping out of the tip. I slid down his body to my knees, and holding his cock upright, I began to slowly lick his balls, then brought my tongue up his shaft, and took him inside my mouth.
I had forgotten what it was like at that age, but I gently sucked on his cockhead for about 30 seconds, and when I first slid my lips down his shaft, the second it entered my throat and came back out again, he groaned, and began shooting his load into my mouth. His cum was really thick, and salty sweet, and my mouth began filling up as his goo kept flowing onto my tongue. As he was finishing I looked up into his eyes and gulped most of it down with him watching me. I drained the last drops out of him, and stood up.
'Let's lay down and relax' I said, and I grabbed our wineglasses and put them on the bed tables, and layed back against the pillow, as he lay down next to me. We had a few sips of wine, and talked a little, but we were soon lightly kissing again, laying side by side facing each other, and as I gently played with his soft cock it quickly got hard again.
I had heard that old joke that young guys can't hold out long, but they can do it often, and I had every intention of testing that theory. I kneeled between his legs and bent down to take him into my mouth, and began sucking him again, using my tongue on his cockhead, and sliding my lips up and down his shaft, and after his cock entered my throat for maybe the 5th time he moaned again, and again blasted my tonsils with his cum. I slurped up all that he gave me, and swallowed it down, and then lay back against the pillow again.
After a few minutes I got up to pee and freshen up, and when I came back he was sitting back on the couch, still naked, surfing the channels with the remote. I got the glasses and poured a little more wine, and then I lay down with my head on his belly and his soft cock in my mouth, and we watched TV together for awhile that way. He finally settled on an old movie and we watched it together for awhile, my head in his lap and his cock in my mouth.
But just a little way into the movie, he began to get hard again, and I just sort of nursed on his cock, gently sucking and licking, but not moving my lips. He began to pump his cock in and out of my lips, slowly at first, and then faster, and without a bit of warning he shot another load of cum into my mouth. I wasn't expecting it this time, and had breathed out just when he blasted, and I had managed to get a few globs of his cum in my nostrils. So as I was sucking the last bit from his cock, I was also sniffing the cum back into my throat from my nostrils, and swallowed the whole gooey mess. He slumped back, but I kept his soft cock in my mouth, and somehow I fell asleep that way, my head on his belly.
I was awakened some time later by a hard cock pushing into my throat, and before I became fully awake I felt hands on the back of my head, and a cock was well in my throat, and cum was dripping back into my mouth. I started to gag, but he quickly pulled back, and said 'sorry, I didn't mean to choke you - but having you sleeping there with a cock in your mouth was too hard to resist'
I was back up to the bathroom, peed, and when I came back out he was laying on the bed again. So I lay down next to him, sleepily, and though I had just leaned over to give him a quick kiss, the next thing I knew we were laying there, kissing, tongues touching.
I was getting really horny by now, but he didn't seem to have any interest in helping me out along those lines. So I said 'let's try something' And I slid halfway down the bed on my back with my feet on the floor, and then looked him in the eyes, opened my mouth wide, and said 'fuck my mouth here' He put his knees on either side of my chest, and leaned forward towards the pillow, and stuck his cock between my lips and began slowly fucking my mouth.
I love that feeling, and as his cock slid in and out of my lips, and I got really hard again, I took out my own cock and began stroking it. He knew I was doing it but couldn't see it, and I think that in itself was a turn on for him, and as his cock slid back and forth across my lips I kept myself on the edge of orgasm. And then I purposely began moaning, which got him going again, and he began to fuck my mouth faster and faster as I stroked myself faster and faster, and he finally thrust down into my face and when his cock entered my throat and released it's load of goo, I gave myself 3 quick strokes and felt cum shooting across my belly as I released my built up load with a small scream.
He pulled out, and I reached for a tissue to wipe myself and tuck myself back in, and at this point we were both exhausted. I looked at the clock and it was 1:30 AM, so I moved up to the pillow, leaned over to give him a quick kiss, and fell asleep on the spot.
Somehow, though, twice more during the night I found myself waking up, seeing his cock, and ended up sucking him till he exploded, though the loads were getting really small by the end.
At 7:30 AM I woke with a start, and realized I had to start getting ready for my meeting. So I jumped out of bed, started coffee, removed my nail polish in the bathroom, and hopped into the shower. About a half hour later I came out of the shower and got dressed in my business suit, and when he woke up I was sitting there drinking coffee, as much of a guy as I ever get, with an attache case sitting on the chair next to me.
I poured him a cup of coffee, but the situation was awkward as we both avoided eye contact completely, and on the way to my meeting downtown I dropped him off back near the bar. It had been a really cool night, but a really strange end to it.
I had my meeting, went back and packed my bags, and was back on the plane hours later - the trip was over.
If you liked this story, please write me: jennyjamestg@hotmail.com