“Travis, please we can’t do this,” I told him in a weak voice with no conviction in my tone as he kissed my neck.
While I told him to stop, I didn’t push him away and my voice held no conviction in it to make him stop. It felt so good to have him kiss my neck. It had been years since a man kissed my neck, to have a man’s arms around my body and hold me as Travis was holding me against his body. To have a man kiss me as we were kissing just seconds before he started kissing my neck.
“Sure we can,” he whispered in my ear. “It’s easy to do this. I put my cock in your pussy and we fuck.”
I could not help but giggle at his reply and then started making whimpering moans as he started to kiss my neck again.
“Please, we shouldn’t do this. It’s not right,” I weakly protested again but I let out a louder moan of pleasure when he started kissing my ear.
I wished he hadn’t done that. Not that it didn’t feel good; that was the problem. It felt too good. I loved having my ears kissed and nibbled on. It turned me on.
“Oh, God, please…please don’t. You’re too young,” I told him. “I can’t do this with a boy so young.”
“I’m nineteen so it’s not illegal,” the boy replied.
I was surprised he was nineteen. I had thought he was maybe seventeen at the oldest. But I was thirty-five at the time the boy was kissing my neck in my hotel room and everyone under twenty-five looked like a teenager to me.
“It’s still wrong,” I told him.
“I like your accent,” he told me as he ignored my protest. “It’s sexy. You’re sexy.”
I speak perfect English and even use English or American slang, but I do have a slight accent. I was born in Tel Aviv and after my two years of active duty in the naval branch of the Israel Defense Forces (IDF), I came to the US with my parents to go to college. I became a US citizen after I graduated college.
Travis continued to kiss my neck and nibble on my ear lobe. I felt his hands cup my butt and gasped as he pulled me even closer and then moaned as he started grinding his pelvis into me. He was much taller than my five foot four inches and his crotch was in my stomach.
Travis started kissing my lips and as if I had no control over my body, I parted my lips and allowed his tongue to enter my mouth. I made another gasp, this time into the boy’s mouth, as his hands lifted the hem of my dress and his hands slid under my pantyhose, and cupped my naked butt.
As if my hand had a mind of its own, I slid it around the boy’s waist, to his crotch, and ran my fingers up and down his hard shaft through the material of his slacks. Once I touched his cock, I knew I would no longer be abler to resist and I would give the boy what he wanted. It had been a long time since I felt a hard penis. I started kissing him more passionately.
Travis sensed he had conquered me and he slid on hand up my back, grabbed a handful of my hair, and pulled my head back. I whimpered from the pain of it.
“I want you to suck my cock, Hannah,” the boy told me.
The tone of his voice had changed. It was no longer the nice, sweet, playful tone he had used all night when he flirted with me. It was now commanding and forceful. Travis pulling my hair and the authoritative voice he used excited me. I was not used to being talked to or treated that way and I found both him pulling my hair painfully and the tone of his voice arousing.
As if I was in a daydream, I didn’t reply but instead got on my hands and knees in front of the young boy. As I was getting on my knees, Travis was unbuckling his belt. Once on my knees, I looked up at Travis as he started unbuttoning his pants. As he pulled them down, my eyes went to his crotch and I waited with anticipation for him to free his cock from his boxer briefs. I had not had a cock in my mouth in a long time. I had not even seen a real cock in a long time.
Just how did I, a thirty-five-year-old divorced woman, end up in my hotel room with a nineteen-year-old boy? A woman who up until that moment considered herself a moral person was about to give a nineteen-year-old boy she just met that day a blowjob? A woman who had not been with a man sexually in just over a year even though she had opportunities to date men ended up surrendering to a nineteen-year-old boy? It all started with my part-time job and hobby as a wedding planner.
My sexual past was very limited. While I dated a couple of boys in what is equivalent to an American senior high school and even gave one oral sex, I did not lose my virginity until I was nineteen and was dating a fellow sailor in the IDF. My next sexual partner was my husband when we started dating in college and then after my divorce one of the men I dated. That did not mean I didn’t enjoy sex. I don’t know why some people think just because a woman is not promiscuous or if she is religious that she does not enjoy sex. I was just not a promiscuous person.
As for being religious, I was not that either. Being Jewish, I did practice Judaism and went to Synagogue, had a Bat mitzvah at thirteen (a Bat mitzvah is a Jewish girl’s Bar mitzvah), and we did practice some of the Jewish laws and celebrated the Jewish religious holidays, but we were not an overly religious family. I even married a Christian man, but he was not religious either and my Jewish family was not upset by me marrying outside our faith.
I was not a sexual prude either. I enjoy sex a great deal and with the few sexual partners I had we had a lot of sex and I often initiated it. I loved giving oral sex and yes I do swallow, but I was never into kinky stuff and my sex life was, as people call it sometimes, vanilla. I did not mind it being vanilla and never once thought of exploring the more kinky side of sex. Yes, I did masturbate also and at thirty-five I owned two sex toys I used to masturbate with; a small vibrator for my clit and a glass dildo with ridges on the shaft. I enjoy intimacy, lovemaking, cuddling, and kissing. I love kissing!
I had to be honest with myself. I was very flattered that a young teenage boy was flirting with me. What thirty-five woman would not be? Yes, I even flirted back, but I thought it was harmless until he kissed me for the first time that night. There was also the taboo of it that excited me and aroused me. His age, the way he kissed me and took control over me, the forcefulness of his kisses, how he insisted he escort me to my hotel room, and how he invited himself into my room.
I started my wedding planning business seven years before that night as just a side job and a hobby. After several weddings, I found out I had a knack for it and soon I was getting more clients and doing destination weddings. I made contacts with caterers and dress designers who recommended me to people.
That weekend I was doing a destination wedding in Asheville, NC. The young couple was local and from the same city, I lived in Virginia but wanted to get married at the Biltmore House. After seeing the prices, they decided on a wedding at another venue in the same city of Asheville. The Biltmore House would have had their wedding planner, which you were required to use, but the venue they chose did not so I was hired based on a recommendation from the woman who was designing and making their wedding cakes.
Travis is the bride’s younger brother, nineteen, tall, very good-looking, and very charming. Travis was also arrogant, which for me added to his being attractive. He was one of the groomsmen. He started flirting with me at the wedding rehearsal and then even more at the rehearsal dinner and party. I won’t go into detail about the flirtations between us, that would take too long, but I may or may not have taken it much further than just harmless flirting. It was just a good feeling for me to have a very attractive nineteen-year-old flirting with me. So yes I may have given him some confidence to ask me if he could come into my hotel room.
His advances became more bold when I was leaving the rehearsal dinner and going back to my hotel room. The fourth floor of the hotel was blocked off for the wedding party and guests, but it was a large wedding and my room was on the fifth floor, and other guests were scattered about the hotel on various floors. I left rather early because I had a lot to do the next day to make sure the wedding went as planned.
As the elevator door was closing and I was headed from the lobby to my room a hand slid in and the doors opened. Travis was standing there with a mischievous grin on his face and he then walked into the elevator. I was surprised to see him. The rehearsal dinner was taking place at another location and not in the hotel. I didn’t notice that Travis didn’t press the button for his floor. I was a little nervous being alone in the elevator with him.
I was nervous because even though the flirtations were harmless, at least on my part, being alone with him made me feel ashamed I was flirting with a young boy who at that time I thought was not even eighteen.
“Not going out with the boys tonight?” I asked as the elevator doors shut.
“They had the bachelor party last weekend,” Travis explained and stepped closer to me. I backed up until my back was pressed against the wall. “They are going to get together in Steve’s room later,” Steve was the groom. “But they are a bunch of assholes so I don’t want to hang out with them.” He grinned at me again in a devilish manner, “Plus I would rather be somewhere else.”
“Oh, where is that?” I asked not knowing at that point what he meant.
Travis moved even closer until he was about two inches from me and his tall frame towered over me. He lifted one arm and put his hand against the elevator wall right above my head.
“Your room,” he told me boldly. The arrogance he showed earlier seemed to be even more than it was before.
I made a nervous laugh but didn’t move. I felt frozen and my legs seemed not to obey my mind. I didn’t even try to move when Travis leaned down and moved in to kiss me. He had to lower his head quite a bit to do so. He was over six feet tall and I am a small, petite woman. I stand only five foot four and have a slender body.
Travis didn’t kiss me, however. Instead, he lifted his other arm, brought his hand up, and brushed my hair away from my face. I had my long, dark brown hair down that night. I may have let out a slight whimper mixed with fear and pleasure. I was not sure because everything happened so fast.
Uneasy fear because the young boy was being so bold with his advances, and pleasure because it had been a long time since someone touched me sensually.
“You are so sexy, Hannah,” Travis told me.
“Th-thank you,” I stammered. I didn’t know what else to say.
Maybe not moving away from his touch encouraged the boy because he leaned in and kissed my lips. For about two seconds I didn’t move and my eyes opened wide at the unwanted kiss but then I opened my mouth, put my arms around his lower back, and started kissing him back. I parted my lips to allow his tongue to enter my mouth.
Travis pressed his larger body against my small body and I felt his hand lift the hem of my dress and didn’t stop him. Clutching my small clutch purse in one hand, I lowered my hands to his butt and pulled him even closer to me. As I felt his hand slid up my thigh and again I didn’t stop him. By then I was sexually aroused, my little nipples were taut with excitement, and I was slightly wet from arousal. I felt Travis’s hand trying to slide under the waist of my pantyhose. He was being rather clumsy about it and instead of getting his hand down them, he pulled them up more so they gave me a slight wedgie in both places.
I was not wearing panties, I never did on the rare occasions I wore pantyhose. Was nothing sexual or trying to be sexy about it and I always wore panties at other times. I disliked wearing pantyhose in general and the only reason I did that night was because they were black tinted to match the cocktail dress I was wearing.
Just as the boy finally got his hand into the waistband of my hose and I was going to stop him I heard the bell of the elevator ding as we got to my floor. Like a boxer losing a round, I was saved by the bell.
As the elevator door opened I quickly adjusted my dress and didn’t say anything as I walked out of the elevator. I was in such a hurry to get away from Travis I didn’t bother to adjust my pantyhose which were slightly wedged in both places. Plus I didn’t want him to see me do that; for some reason, men think that is sexy when a girl does that. I heard Travis’s footsteps behind me, stopped, looked over my shoulder, and saw him grinning at me.
“I’m a gentleman and my father always told me to walk a lady to the door,” he told me.
I doubted he was a gentleman because he was not acting like one in the elevator. I didn’t say anything and started walking to my hotel room as I got the card key out of the clutch purse. Once at the door, I fumbled with the key in the lock because I was nervous and my hand was shaking. The damn thing would not work!
Travis placed his large hand over my small, delicate hand took the key away, and opened the door for me.
“Thank you,” I said in an almost whisper as he opened the door.
“Maybe I can come in and we can hang out some,” he suggested. “Everyone is still at the rehearsal dinner and I am sharing a room with my dad, and he has been drinking and when he drinks he starts to give me bullshit about what am I going to do with my life. I would rather not hear that and I can hang out with you until I think he has passed out.”
“I don’t think that is a good idea,” I told him.
“No funny business, I promise,” he replied. “We can just hang out and talk for a while. I like talking to you. You are cool.”
Cool was never the way I had ever been described. “Ok,” I blurted out, “but no funny business like you said.”
I don’t know why I agreed to let him come into my room or maybe I did. Later that night I thought about why I let Travis into my room and I concluded it was because I enjoyed him flirting with me and him saying I was cool. I know it was not because I was going to have sex with the boy. Sure I thought about it, I am only human and it had been a long time since I had sex and he was so good-looking and a very good kisser, but he was still much too young for me. Giving into him for sex came only moments later.
We walked into the room and Travis didn’t waste any time. As soon as we were in the middle of the room I turned and was going to tell him to sit in the chair in the room while I went into the bathroom to change into something more comfortable. My more comfortable was not anything sexy; far from it. It was just a pair of oversized lounge pants and an oversized tee-shirt. I wanted to get out of my wedged-up pantyhose.
When I turned around I saw Travis was only inches away from me. He grabbed me and pulled me to him and started kissing me again. I froze once more but as like in the elevator I soon started kissing him back and put my arms around his waist. Travis started kissing my neck and I finally started to protest.
“Uhh…you promised…ohh, God that feels good…you promised no funny business,” I told him but did not push him away. His kissing of my neck did feel good.
“And there won’t be no funny business,” he whispered in my ear. “When I fuck you it won’t be funny.” He said with arrogance and confidence in his voice.
“Travis, please we can’t do this,” I told him in a weak voice with no conviction in my tone as he kissed my neck.
While I told him to stop, I didn’t push him away and my voice held no conviction in it to make him stop. It felt so good to have him kiss my neck. It had been years since a man kissed my neck, to have a man’s arms around my body and hold me as Travis was holding me against his body. To have a man kiss me as we were kissing just seconds before he started kissing my neck.
“Sure we can,” he whispered in my ear. “It’s easy to do this. I put my cock in your pussy and we fuck.”
I could not help but giggle at his reply and then started making whimpering moans as he started to kiss my neck again.
“Please, we shouldn’t do this. It’s not right,” I weakly protested again but I let out a louder moan of pleasure when he started kissing my ear.
I wished he hadn’t done that. Not that it didn’t feel good; that was the problem. It felt too good. I loved having my ears kissed and nibbled on. It turned me on.
“Oh, God, please…please don’t. You’re too young,” I told him. “I can’t do this with a boy so young.”
“I’m nineteen so it’s not illegal,” the boy replied.
“It’s still wrong,” I told him.
“I like your accent,” he told me as he ignored my protest. “It’s sexy. You’re sexy.”
Travis continued to kiss my neck and nibble on my ear lobe. I felt his hands cup my butt and gasped as he pulled me even closer and then moaned as he started grinding his pelvis into me. He was much taller than my five foot four inches and his crotch was in my stomach.
Travis started kissing my lips and as if I had no control over my body, I parted my lips and allowed his tongue to enter my mouth. I made another gasp, this time into the boy’s mouth, as his hands lifted the hem of my dress and his hands slid under my pantyhose, and cupped my naked butt.
As if my hand had a mind of its own, I slid it around the boy’s waist, to his crotch, and ran my fingers up and down his hard shaft through the material of his slacks. Once I touched his cock, I knew I would no longer be abler to resist and I would give the boy what he wanted. It had been a long time since I felt a hard penis. I started kissing him more passionately.
Travis sensed he had conquered me and he slid on hand up my back, grabbed a handful of my hair, and pulled my head back. I whimpered from the pain of it.
“I want you to suck my cock, Hannah,” the boy told me.
The tone of his voice had changed. It was no longer the nice, sweet, playful tone he had used all night when he flirted with me. It was now commanding and forceful. Travis pulling my hair and the authoritative voice he used excited me. I was not used to being talked to or treated that way and I found both him pulling my hair painfully and the tone of his voice arousing.
As if I was in a daydream, I didn’t reply but instead got on my hands and knees in front of the young boy. As I was getting on my knees, Travis was unbuckling his belt. Once on my knees, I looked up at Travis as he started unbuttoning his pants.
When I was on my knees I stared at the boy’s crotch and was not surprised to see that he was aroused. His hard penis was pressing against his slacks. I waited excitedly for him to pull down his pants and underwear so I could see his erect penis.
Travis quickly unbuckled his belt, unbuttoned his trousers, and pulled both his pants and underwear down to his upper thighs. I then pulled them down to his ankles and took a moment to admire his erect penis before I put it in my mouth. I had not even seen a man’s penis in a long time.
I liked the way a man’s penis looked and thought it was sexy. Travis’ cock was sexy. It was average size, maybe about half an inch longer than the 3 lovers I had. I didn’t measure it of course but I would estimate about seven inches long. The girth of it was nice also. Not huge but again about average. I liked the smoothness of his shaft and how it formed perfectly symmetrical with the tip.
I slowly reached out and took his penis in my hand and started to run it up and down the shaft, gliding my fingers over it. Once I touched it I knew there was no backing out and I didn’t want to. I wanted to touch it, stroke it, and put it in my mouth.
“Well, what are you waiting for? A written invitation? Get your mouth around it and get to work.” Travis’s voice was once again full of authority. The playful and flirty tone he had used previously with me was gone.
“Ok, but just this,” I told him as I looked up at his face. “I am not going to have sex with you and you can’t tell anyone.”
Travis didn’t answer but placed his hand on the back of my head and guided me to his cock. I parted my lips and took him into my mouth and started to give him a blow job.
Ever since the first time I gave a blow job to a guy I liked it a great deal. I enjoyed the masculine smell and taste and the feeling of penis in my mouth. It turned me on. I have heard from my married female friends that they stopped having oral sex regularly once they got married or several years into the marriage and heard a lot of married women do the same. I don’t know if that’s true or not, but I did know that was not true for me. I loved giving blow jobs and did it often to my husband and the two other men I had been intimate with. I think over the years I had gotten very good at my technique. While it had been a long time since I gave a blow job, I figured it was like riding a bike.
I started on Travis’s cock like I always started on a man; I took just the head into my mouth, formed a tight seal with my lips, and ran my tongue over the tip while it was in my mouth. I could already taste the boy’s pre-cum. Travis moaned out in pleasure.
The abundance of his precum made me realize the boy was not going to last long and I wanted to enjoy him being in my mouth so I took it slow. I teased the head with my tongue for a while before I took the rest of him in my mouth and down my throat. I was good at deep-throating and had not had a gag reflex when I gave oral sex since I was about twenty and the boy’s size was nothing I knew I could not handle.
Travis got tired of my teasing and he gave my head a gentle push and I knew what he wanted me to do. I took his cook deeper into my mouth and then deep-throated the boy until my face was pressed against the pubic hairs surrounding his penis. I held myself there for a few seconds.
“Ugh, fuck, Hannah,” Travis moaned out
I then pulled my head back and started to bob my head back and forth rapidly and again Travis moaned out from pleasure.
As I worked his cock with my mouth, I started stroking his shaft with my right hand and let my saliva escape my mouth to cover his erect penis to lubricate it. I liked giving wet, sloppy blowjobs.
“Look at me while you suck my cock,” he told me.
I looked up at the boy and he brushed the hair away from my face so he could watch me. I kept up a steady, rapid pace and kept stroking his shaft and Travis started moaning louder. I knew he was about to orgasm. I felt his body tighten and heard his moans get louder. I was making soft, whimpering moans as I gave the boy a blow job.
“Uhhh, fuck, yes,” the boy grunted out loudly, his hand grabbed my hair, and he exploded his fluid into my mouth.
Yes, I swallow and I like to swallow. I enjoy the taste of a man’s sex fluid and the feeling of it shooting into my mouth and down my throat. I kept sucking and stoking as I swallowed the boy’s cum. Travis came a lot and his cum was thick and warm and there was a great deal of it, but I didn’t let any spill out of my mouth.
His body jerked and his hips thrust into me as he orgasmed and I kept jerking his cock to get more of his delicious fluid into my mouth. After the boy was finished I pulled my mouth away, licked up and down his hard shaft, and then used my hand to coax more of his cum from him and licked the tip to get it all. I kept licking and sucking the tip until Travis pulled my head back by my hair.
“Damn, Hannah, you sure know how to suck dick,” he told me as I looked up at him. “Fuck, you’re a great cock sucker. That was awesome. My girlfriend doesn’t let me cum in her mouth.”
I didn’t like being talked to that way or being called a cock sucker, but I didn’t say anything as I got off my knees and stood up and wiped my mouth.
“Ok, Travis, you got what you wanted,” I told the boy. “I think you should leave now.”
I did feel ashamed of myself for what I did. Not just because the boy was so much younger than me, but also because I never had done anything like that; I had never just given a man a blow job or done anything sexual with a man I just met. I didn’t do anything sexual besides kissing until we had dated for a while.
My first boyfriend in high school I dated for about a year before I gave him my first blowjob and let him touch my breast or finger my pussy. The next man when I was nineteen and in the IDF it took about two months before we did anything sexual besides kissing and letting him fondle my small breasts and then I gave him oral sex. We dated for five months before I lost my virginity to him. My ex-husband I did have sex with after three weeks of dating, and that was quick for me.
Even though I felt shame for what I just did I could not deny to myself that I didn’t enjoy it and also that I was very sexually aroused. It was hard to try and convince I was not turned on because my pussy was very wet, my clit felt like it was throbbing, and my pussy felt a strong urge to be penetrated. I knew I was going to masturbate after the boy left the room. I regretted not bringing my dildo.
As all that was running through my mind, I heard Travis chuckle, felt his hand grab my butt cheeks, and lifted me off the floor. I wrapped my arms around his neck to brace myself so I would not fall.
“No, Hannah, we are not done yet,” he told me in an arrogant, confident tone. “I am going to fuck you now.”
Before I could protest and tell him no, Travis carried me to the bed.
