Wife got suspicious...
I ended up having a relationship with a married man I'll call Tom. I didn't know he was married until he told me we had to stop kind of like dating because his wife was getting suspicious. We met online, he was a guy who liked crossdressers like me. He was pretty cute, lean and trim and he liked sucking cock, fucking and cum. The first time we met was at some office building where I figured he was like an executive or something because he was wearing a tie, dress shirt and slacks when I got there. It was a Saturday evening and the building was pretty empty. He had keys and we ended up moving from this office - where we shared are first tentative kiss - to a storage room with like old office furniture in it. I mean it had a nice couch and a couple of comfy chairs in it and had probably been used by a few different couples for kinky encounters. I was wearing jeans, a hoodie and tennis shoes which covered up my white silky panties, a sheer silky bra, some white thigh highs and a garter belt. I was nervous as hell until we started making out and undressing.
He was a good kisser to because he was sucking my tongue and my lips, just this alone was driving me wild! When I took off my hoodie, he slipped behind me, slowly pulling and twisting my nipples through my silky bra, nibbling on my ear and kissing my neck. This was driving me crazy, making me rock hard and giving me sensations like I never experienced with a woman before. One of his hands kept playing with my rock hard nipples, his other started rubbing my hard cock, the sensation of it rubbing against my jeans and silky panties was mind blowing. I then started feeling his hard cock rubbing against my ass and I thought, if he wants to fuck me tonight, I am saying YES and losing my virginity at the same time!! Again, this was like nothing that I experienced before! As our pants dropped to the floor, he kept on caressing my rock hard cock through my silky panties and rubbing my my freshly shaved legs through my thigh high stockings. I got on my knees and started to kiss his rock hard cock through his underwear, licking the wet spot that had formed while we were making out. Then I did something that I still enjoy to this day, slowly pulling down his underwear like a kid opening a present and waiting for his surprise to pop out. When it did, I thought hmm... maybe this might be a little too big to think about losing my virginity tonight! But as I started to kiss his eight inch cock, slowly licking it and feeling it getting harder in my mouth as I starting sucking on it, I was like nope, it's happening tonight baby!! And we had discussed this online before we met, if he felt good about it and so did I , we'd give it a try. He slowly laid me down on the couch, both of us kissing and caressing each other as our hard cocks were rubbing together - another sensation that was new to me! He slowly worked his way down my neck and pulling down one side of my bra, started kissing and sucking on my nipples. This was pre hormone days so my "boobs" weren't very big, just regular guy boobs BUT man, were they sensitive - especially tonight! He slowly started kissing down my stomach, working his way down to my panty clad bulge, kissing and licking the wet spot I had on my panties. He kept caressing, licking and kissing my rock hard cock through my panties while sliding his hand down towards my ass. He carefully pulled my panties down until they caught on my balls and started eagerly sucking on my cock.
I almost shot my load right then and there but he remembered something else we had talked about online - I had never sucked a guys cock and had him come in my mouth. Yes, I had tasted another guys cum when I was younger, when we were jerking off at my cousins house. Typical early teen stuff, head up to my cousins room, lock the door and some Penthouse magazines came out from the hiding spot and soon the four of us our jerking off to beautiful women. By this time, I was crossdressing to but more on that later. We would reach over and grab another's guys cock, jerking it and rubbing them. I thought it was kind of weird but I got more turned on by grabbing his friend's cock then I did by the naked chicks. Along with some unscented oil lube, a couple of clean hand towels were brought out for clean up. It was during one of these jerk off sessions that my cousins friend shot his load and a good portion of it landed on my thigh. While he was looking for a hand towel, I wiped up some of his cum with my fingers stuck it in my mouth. It was right then and there I learned that I loved the taste of cum! After that, anytime I was jerking myself off, I always ate my cum. Fast forward 15 years and I hook up with this pantyhose guy who I met up with three times. He was no way into cum at all, his or mine. We would suck each other's cock and make out with each other but no cum in the mouth, his rules, not mine. Surprised I still hooked up with him another two times.
I told Tom that if we ever met up, I wanted him to come in my mouth and I was going to check that off the list tonight!! Slowly, Tom stood up, grabbed a pillow, put it down on the floor and told me to get on my knees. I was more than willing and able to follow those instructions! That and being on my knees, sucking his cock made me feel more like the woman I wanted to be. I started off slow, following Tom's instructions, licking, kissing and sucking his beautiful cock. Pretty soon, I could feel him tense up and I knew my treat was coming. He had me stop sucking and kneel there with my mouth open as he jerked himself to a climax. His first shot hit me on my face but the rest of it went into my hungry mouth! He told me to stay still as he continued to pull on his cock, milking every last drop of his tasty cum into my open mouth. Tom told me to keep my mouth open because he wanted to see all of his cum in there. He then told me to swirl that around in my mouth with my tongue while he used his finger to wipe the cum off my face and deposit that into my mouth as well. I swirled his cum around in my mouth, I blew a few bubbles with it and then he finally let me swallow it!! He slowly had me get up from my knees, stopping to kiss his cock, start kissing his stomach and then he gently cupped my chin in his hand and we started kissing again, deep, wet kisses. He slowly turned around and laid back on the couch, pulling me on top of him. We continued kissing and then he stopped and looked at me, "Well, what did you think about your first load of cum in your mouth?" I said, "God, I hope this is the first of many, many more loads I get in my mouth!" We both laughed and then I put my head on his chest, Tom saying that the night is still young. He was right because we started kissing again and Tom was like, "I can feel your rock hard cock rubbing mine, keep doing that it feels so good." Tom then grabbed my panty clad ass cheeks and started pull me down on him, my hard cock grinding against his body as we passionately kissed. The more we did that, the harder he was getting and the closer I was getting to blowing my load on him. I started tensing up and Tom was like, "Are you ready to cum baby?" "Yes, YES!" I moaned. Tom was like, cum on my cock and on my stomach!! I then sat up between his legs and furiously jerked my cum all over his cock and stomach, collapsing into a heap next to him!! He gently kissed me as he ran his fingers through my hair and hugging me. He then looked me in the eye and said, "Well, get down there and clean up your mess. I want you to lick every drop of your cum off me and swallow it baby!" Who was I to argue with orders like that!! ?❤️?
We were all over that furniture, first on the couch and then on the chairs. It was on one of the chairs where he fucked me that first night, positioning me facing the back of the stuffed chair, kneeling on the cushion with my legs spread out, my ass stuck high in the air. Again, I was having some mixed feelings about losing my virginity to his eight inch cock but it wasn't gianormishly thick around. After he positioned me in the chair, I still had my panties on. He stood behind me and started rubbing his cock against my silky panty clad ass, sending shivers down me. "Well, I am not going to pressure you to do this, we are having a lot of cum shooting sex without it?" As he continued to rub his cock against my ass, I was like,"Fuck it, let's do this! I know you'll take it slow." He slipped my panties off and started rubbing his hard cock against my now bare ass, further turning me on. His then leaned down and start to kiss and lick me. He then asked me if I had ever been rimmed before. I told him that I didn't even know what that meant. "I'll show you, let me know if you like it." Tom the proceeded to rim my tight asshole, slowly at first and more aggressively after I started to moan. He did this for nearly 15 minutes. I had never been rimmed before and it was all I could do to keep from shouting with pleasure, still worried that some janitor or security guard would hear my moans! He slowly starting pushing his gorgeous cock in my ass, patiently asking me how much further he should put it in. Pretty soon, he was burying all eight inches of it deep into my ass, feeling his balls slapping against my ass cheeks and me getting harder and harder with each thrust of his hips. By now, I was biting my lip, then my finger, hearing his muffled moans as he kept pounding my ass as he pulled on my garter belt. I could start to feel him tense up as he pulled his cock from my ass, him telling me to get on my knees again. I quickly complied, my rock hard cock throbbing as I eagerly awaited the treat that he was going to fill my mouth with! I opened my mouth just as the first shot of his cum shot from his cock, splashing into the back of my throat. He filled my mouth again as I slowly rubbed his beautiful cock against my lips, still feeling his cock pulsating and twitching in my hand. As I swallowed his load, he slowly pulled me up and started kissing me, licking his cum from my lips as he slowly tugged on my rock hard cock with one hand while he ran his fingers through my hair with the other. He then whispered, "Are you ready?" I nodded yes as he got on his knees, slowly licking the precum from the tip of my cock as he gently and eagerly took my cock into his mouth. He grabbed my ass cheeks, then my garter belt as he deep throated my seven inch man pussy while I gently grabbed the back of his head and started thrusting my cock into his mouth. It was only a couple of minutes before my stomach and thighs started twitching, Tom pulling my cock from his mouth as he stroked my cock until I shot my creamy load on his face. He slowly rubbed my cock on his lips and the deep throated me again until he milked the last of my cum from my cock. This slowly dropped me to my knees, gently kissing and licking my cum from his face and lips. I remember this like it was yesterday mainly because I never expected to have my first real gay sex in a storage room in an office building!! I swallowed loads of cum that night including my own EXCEPT for some cum that got in my hair. I ended up going grocery shopping after our sex session without realizing that I had some jizz in my hair and on my ear! Oops! Then again, I was grocery shopping while wearing jeans, tennis shoes, a hoodie along with panties with a big wet cum spot on them, thigh highs and a bra - I took the garter belt off and stashed that in my car - so really, what was a little jizz in my hair at this point?
Anyway, we started meeting each other at different motels, twice a month for four months straight. We'd meet a little after noon on a Thursday and fool around until five, each of us having to get back home or to the office. I learned a lot sexually from him, even learning how to deep throat cock, though him grabbing the back of head and jamming my face down on his cock out of the blue probably helped. By the time we met around the fourth time, I was burying my nose in his pubic hair without gagging on his eight inch cock and I LOVED it! I would also wear different lingerie to our hookups, wearing a teddy one time, a baby doll the next and even wearing a maid outfit, sadly on our last get together. We would get hot and heavy the first couple of hours and then cuddle for a bit or take a long hot sexy shower together. Yes, dropping the soap was a lot of fun as it usually ended with me getting my face jammed against the shower wall as he pounded me in my ass with his cock and filling me with more of his cum. I figured with the cuddling, the long wet kisses, the talking and the gentle caressing we were doing that maybe this might be something a little more serious than just hooking up for awesome sex but I was wrong. I mean he was telling me about some of the other guys he had fooled around with and I told him of the one weird relationship I had with the pantyhose guy (more on that in a later post.) He for sure knew I was single and I figured both of us were keeping our sexuality and, in my case, crossdressing, from becoming public knowledge. I mean it sucked but I wasn't going to go blabbing to his wife about us so I sucked it up and put it down as a learning experience, which, sexually, it was. So I put my maid outfit in my bag, took a long hot shower, lathering up with some sexy feminine scented body wash, drying myself off and slipping into a new sexy pair of pink panties and a pair of pantyhose while I crashed on the bed for a bit. The new panties and the pantyhose got me excited again, my precum soaking through both of them. I freed my cock from both the panties and the pantyhose and started stroking it, thinking about how much I loved sucking Tom's gorgeous cock. I ended up blowing another load of my hot cum into my cupped hand, slowly dripping it into my mouth, rubbing it on my lips, swishing it around in my mouth, enjoying the sweet salty taste and then swallowing it. Little did I realize that this was the best it was going to get for at least another eight months...
Kellygirl ❤️
He was a good kisser to because he was sucking my tongue and my lips, just this alone was driving me wild! When I took off my hoodie, he slipped behind me, slowly pulling and twisting my nipples through my silky bra, nibbling on my ear and kissing my neck. This was driving me crazy, making me rock hard and giving me sensations like I never experienced with a woman before. One of his hands kept playing with my rock hard nipples, his other started rubbing my hard cock, the sensation of it rubbing against my jeans and silky panties was mind blowing. I then started feeling his hard cock rubbing against my ass and I thought, if he wants to fuck me tonight, I am saying YES and losing my virginity at the same time!! Again, this was like nothing that I experienced before! As our pants dropped to the floor, he kept on caressing my rock hard cock through my silky panties and rubbing my my freshly shaved legs through my thigh high stockings. I got on my knees and started to kiss his rock hard cock through his underwear, licking the wet spot that had formed while we were making out. Then I did something that I still enjoy to this day, slowly pulling down his underwear like a kid opening a present and waiting for his surprise to pop out. When it did, I thought hmm... maybe this might be a little too big to think about losing my virginity tonight! But as I started to kiss his eight inch cock, slowly licking it and feeling it getting harder in my mouth as I starting sucking on it, I was like nope, it's happening tonight baby!! And we had discussed this online before we met, if he felt good about it and so did I , we'd give it a try. He slowly laid me down on the couch, both of us kissing and caressing each other as our hard cocks were rubbing together - another sensation that was new to me! He slowly worked his way down my neck and pulling down one side of my bra, started kissing and sucking on my nipples. This was pre hormone days so my "boobs" weren't very big, just regular guy boobs BUT man, were they sensitive - especially tonight! He slowly started kissing down my stomach, working his way down to my panty clad bulge, kissing and licking the wet spot I had on my panties. He kept caressing, licking and kissing my rock hard cock through my panties while sliding his hand down towards my ass. He carefully pulled my panties down until they caught on my balls and started eagerly sucking on my cock.
I almost shot my load right then and there but he remembered something else we had talked about online - I had never sucked a guys cock and had him come in my mouth. Yes, I had tasted another guys cum when I was younger, when we were jerking off at my cousins house. Typical early teen stuff, head up to my cousins room, lock the door and some Penthouse magazines came out from the hiding spot and soon the four of us our jerking off to beautiful women. By this time, I was crossdressing to but more on that later. We would reach over and grab another's guys cock, jerking it and rubbing them. I thought it was kind of weird but I got more turned on by grabbing his friend's cock then I did by the naked chicks. Along with some unscented oil lube, a couple of clean hand towels were brought out for clean up. It was during one of these jerk off sessions that my cousins friend shot his load and a good portion of it landed on my thigh. While he was looking for a hand towel, I wiped up some of his cum with my fingers stuck it in my mouth. It was right then and there I learned that I loved the taste of cum! After that, anytime I was jerking myself off, I always ate my cum. Fast forward 15 years and I hook up with this pantyhose guy who I met up with three times. He was no way into cum at all, his or mine. We would suck each other's cock and make out with each other but no cum in the mouth, his rules, not mine. Surprised I still hooked up with him another two times.
I told Tom that if we ever met up, I wanted him to come in my mouth and I was going to check that off the list tonight!! Slowly, Tom stood up, grabbed a pillow, put it down on the floor and told me to get on my knees. I was more than willing and able to follow those instructions! That and being on my knees, sucking his cock made me feel more like the woman I wanted to be. I started off slow, following Tom's instructions, licking, kissing and sucking his beautiful cock. Pretty soon, I could feel him tense up and I knew my treat was coming. He had me stop sucking and kneel there with my mouth open as he jerked himself to a climax. His first shot hit me on my face but the rest of it went into my hungry mouth! He told me to stay still as he continued to pull on his cock, milking every last drop of his tasty cum into my open mouth. Tom told me to keep my mouth open because he wanted to see all of his cum in there. He then told me to swirl that around in my mouth with my tongue while he used his finger to wipe the cum off my face and deposit that into my mouth as well. I swirled his cum around in my mouth, I blew a few bubbles with it and then he finally let me swallow it!! He slowly had me get up from my knees, stopping to kiss his cock, start kissing his stomach and then he gently cupped my chin in his hand and we started kissing again, deep, wet kisses. He slowly turned around and laid back on the couch, pulling me on top of him. We continued kissing and then he stopped and looked at me, "Well, what did you think about your first load of cum in your mouth?" I said, "God, I hope this is the first of many, many more loads I get in my mouth!" We both laughed and then I put my head on his chest, Tom saying that the night is still young. He was right because we started kissing again and Tom was like, "I can feel your rock hard cock rubbing mine, keep doing that it feels so good." Tom then grabbed my panty clad ass cheeks and started pull me down on him, my hard cock grinding against his body as we passionately kissed. The more we did that, the harder he was getting and the closer I was getting to blowing my load on him. I started tensing up and Tom was like, "Are you ready to cum baby?" "Yes, YES!" I moaned. Tom was like, cum on my cock and on my stomach!! I then sat up between his legs and furiously jerked my cum all over his cock and stomach, collapsing into a heap next to him!! He gently kissed me as he ran his fingers through my hair and hugging me. He then looked me in the eye and said, "Well, get down there and clean up your mess. I want you to lick every drop of your cum off me and swallow it baby!" Who was I to argue with orders like that!! ?❤️?
We were all over that furniture, first on the couch and then on the chairs. It was on one of the chairs where he fucked me that first night, positioning me facing the back of the stuffed chair, kneeling on the cushion with my legs spread out, my ass stuck high in the air. Again, I was having some mixed feelings about losing my virginity to his eight inch cock but it wasn't gianormishly thick around. After he positioned me in the chair, I still had my panties on. He stood behind me and started rubbing his cock against my silky panty clad ass, sending shivers down me. "Well, I am not going to pressure you to do this, we are having a lot of cum shooting sex without it?" As he continued to rub his cock against my ass, I was like,"Fuck it, let's do this! I know you'll take it slow." He slipped my panties off and started rubbing his hard cock against my now bare ass, further turning me on. His then leaned down and start to kiss and lick me. He then asked me if I had ever been rimmed before. I told him that I didn't even know what that meant. "I'll show you, let me know if you like it." Tom the proceeded to rim my tight asshole, slowly at first and more aggressively after I started to moan. He did this for nearly 15 minutes. I had never been rimmed before and it was all I could do to keep from shouting with pleasure, still worried that some janitor or security guard would hear my moans! He slowly starting pushing his gorgeous cock in my ass, patiently asking me how much further he should put it in. Pretty soon, he was burying all eight inches of it deep into my ass, feeling his balls slapping against my ass cheeks and me getting harder and harder with each thrust of his hips. By now, I was biting my lip, then my finger, hearing his muffled moans as he kept pounding my ass as he pulled on my garter belt. I could start to feel him tense up as he pulled his cock from my ass, him telling me to get on my knees again. I quickly complied, my rock hard cock throbbing as I eagerly awaited the treat that he was going to fill my mouth with! I opened my mouth just as the first shot of his cum shot from his cock, splashing into the back of my throat. He filled my mouth again as I slowly rubbed his beautiful cock against my lips, still feeling his cock pulsating and twitching in my hand. As I swallowed his load, he slowly pulled me up and started kissing me, licking his cum from my lips as he slowly tugged on my rock hard cock with one hand while he ran his fingers through my hair with the other. He then whispered, "Are you ready?" I nodded yes as he got on his knees, slowly licking the precum from the tip of my cock as he gently and eagerly took my cock into his mouth. He grabbed my ass cheeks, then my garter belt as he deep throated my seven inch man pussy while I gently grabbed the back of his head and started thrusting my cock into his mouth. It was only a couple of minutes before my stomach and thighs started twitching, Tom pulling my cock from his mouth as he stroked my cock until I shot my creamy load on his face. He slowly rubbed my cock on his lips and the deep throated me again until he milked the last of my cum from my cock. This slowly dropped me to my knees, gently kissing and licking my cum from his face and lips. I remember this like it was yesterday mainly because I never expected to have my first real gay sex in a storage room in an office building!! I swallowed loads of cum that night including my own EXCEPT for some cum that got in my hair. I ended up going grocery shopping after our sex session without realizing that I had some jizz in my hair and on my ear! Oops! Then again, I was grocery shopping while wearing jeans, tennis shoes, a hoodie along with panties with a big wet cum spot on them, thigh highs and a bra - I took the garter belt off and stashed that in my car - so really, what was a little jizz in my hair at this point?
Anyway, we started meeting each other at different motels, twice a month for four months straight. We'd meet a little after noon on a Thursday and fool around until five, each of us having to get back home or to the office. I learned a lot sexually from him, even learning how to deep throat cock, though him grabbing the back of head and jamming my face down on his cock out of the blue probably helped. By the time we met around the fourth time, I was burying my nose in his pubic hair without gagging on his eight inch cock and I LOVED it! I would also wear different lingerie to our hookups, wearing a teddy one time, a baby doll the next and even wearing a maid outfit, sadly on our last get together. We would get hot and heavy the first couple of hours and then cuddle for a bit or take a long hot sexy shower together. Yes, dropping the soap was a lot of fun as it usually ended with me getting my face jammed against the shower wall as he pounded me in my ass with his cock and filling me with more of his cum. I figured with the cuddling, the long wet kisses, the talking and the gentle caressing we were doing that maybe this might be something a little more serious than just hooking up for awesome sex but I was wrong. I mean he was telling me about some of the other guys he had fooled around with and I told him of the one weird relationship I had with the pantyhose guy (more on that in a later post.) He for sure knew I was single and I figured both of us were keeping our sexuality and, in my case, crossdressing, from becoming public knowledge. I mean it sucked but I wasn't going to go blabbing to his wife about us so I sucked it up and put it down as a learning experience, which, sexually, it was. So I put my maid outfit in my bag, took a long hot shower, lathering up with some sexy feminine scented body wash, drying myself off and slipping into a new sexy pair of pink panties and a pair of pantyhose while I crashed on the bed for a bit. The new panties and the pantyhose got me excited again, my precum soaking through both of them. I freed my cock from both the panties and the pantyhose and started stroking it, thinking about how much I loved sucking Tom's gorgeous cock. I ended up blowing another load of my hot cum into my cupped hand, slowly dripping it into my mouth, rubbing it on my lips, swishing it around in my mouth, enjoying the sweet salty taste and then swallowing it. Little did I realize that this was the best it was going to get for at least another eight months...
Kellygirl ❤️
2 months ago
