This is a multi-part story and to avoid getting beaten up by the category police it will span several categories as we go along, starting with “first time”. We appreciate your comments even the nasty ones, in most cases the nasty ones demonstrate how lonely some people really are and we truly feel sorry for them. Please vote and tell us what you think. CD
My name is Sylvia, I grew up on Cape Cod and now I am a thirty-nine-year-old widow living in Boston. Financially, I am secure, you could say I am independently wealthy, but I will get into that later in the story. I only go to work when I want to, sometimes only a few hours a week.
Because, I don’t have to spend much time at work, I have time to do things like working out five times a week and spending time at the spa getting massages, facials, nails and whatever else might strike my fancy. For the most part I hate shopping, so I have an assistant that takes care of that for me. The only store I frequent often is my favorite lingerie shop in Boston, which I will also get into that later in the story.
At thirty-nine I have been told that I am one fine looking lady, I respond to the compliment with a, “Thank you.” I have to admit the hard work has paid off for me, I do look good. Oh, who am I kidding, I’m fucking hot, I can stand up to almost any 25-year-old babe out there. I am 34D-23-34 and stand 5’6″. My abs are solid, my ass is round and my boobs are natural and firm. My brown hair is long and straight. I will admit I might have a couple of mild crowsfeet on my brown eyes. Oh, and I forgot to mention, the other spa service I have utilized is laser hair removal, my pussy and ass are as smooth as the day I was born. So by now I must sound like a total cunt.
I have four fetishes, I love lingerie, sucking cock, gentleman and hairless bodies. Sorry, let me rephrase that, I like men with no hair on their bodies, minimal hair is ok if it is perfectly manscaped. A perfect evening is one that I am wearing beautiful lingerie with a cock in my mouth that belongs to a man that is perfectly manscaped or as smooth as the day he was born but most importantly, that man must be a gentleman.
My story begins.
My husband, Baxter, and I had been married for seven years when he tragically died in an accident while riding his bicycle in a one-hundred-mile road race, ten years ago.
Baxter and I were married before we graduated from the same college. We met in our freshman year when we were both riding in a charity bike ride event that went all around Boston. Baxter was the perfect gentlemen in every regard. We had not met yet when he had a problem with one of the wheels on his bicycle. I was riding behind him when he had to stop suddenly and I rode right up his backside.
I really don’t know whose fault it was, but as is typical, I would have expected heated tempers from at least one of us. We were both on the ground with a couple of scrapes but nothing horribly serious.
We looked at each other making eye contact and it was like magic. We both knew. If you ever considered love at first site, this was it. Instead of being upset, we were both apologizing to the other while helping one another up.
Baxter’s bike was not rideable and he had a four mile walk back to his dorm. My bike was probably just fine, but I made a big deal out of it not feeling right, so I would have to walk back as well.
We talked the entire way and I could not get over how respectful Baxter was to me and everyone we encountered. When we arrived back on campus, he escorted me back to my dorm and helped me get my bike put away. He said he was not sure who was the cause of our little bump on the ride but he was sure happy it happened. He said, have a nice evening and we went our separate ways.
I went in my dorm and I could not get this amazing person off my mind. I had to wonder why he didn’t ask me for my number or try to come in. So far, all of the guys I have met in collage have the same mind set. Basically, they didn’t much care what your name was but as long as we could both breath, we must have something in common, so we should fuck. Baxter was different.
Bottom line is, I’m still a virgin. Now, that does not mean I’m a prude. I love performing oral sex, I have certainly had my share of practice and have been told my blow job skills are second to none. Of course, that is coming from guys who’s cum is dripping out of my mouth, so take it for what it is worth. I have also been known to do a pretty good lap dance, I’m not real proud of it but I danced for three guys once, giving each of them a blow job at the end. There is just something about sucking cock and getting a mouth full of sperm that simply turns me on.
My pussy has never been touched by a man. In high school a girlfriend and I had oral sex a few times. We were not a couple; it was more like we were just trying this thing that everyone was talking about. We both agreed that It was very sexy, it felt wonderful and we were kolej escort both happy that it happened but it was not for either of us. I will admit, I have enjoyed my sexual experiences and as hypocritical as it might be, I would really like my first-time being touched by a man to be with a guy that I care about at least a little bit.
It got me to thinking that maybe Baxter isn’t into girls. If that is the case, maybe I could convert him, oh who the fuck am I kidding. I know there is some guy out there that will be very lucky to get Baxter.
I could not get Baxter off my mind, everywhere I go out on campus, I have been looking for him with no success. When I go to bed at night, I lay there thinking about how handsome he is and how much of a gentleman he was. I will admit, my fingers have been making their way to my pussy as I am thinking about how nice it would be to have Baxter as my first.
Then it finally happened, we saw each other across the common and both smiling from ear to ear headed towards one another. We each shared the obligatory hello than we embraced. He was strong and I felt secure in his arms. Without saying another word, we shared eye contact much as when we met and we simultaneously went for a gentle kiss.
Baxter asked if I had time to go get a coffee. I said sure, I didn’t tell him I would be missing my English class. We walked over to the coffee house and when we arrived, Baxter being the gentlemen that I already knew he was, opened to door and helped me to a seat. Before we knew it, we had been sitting there for over 4 hours and we needed to leave. Baxter of course, picked up the bill.
It was about six months of dating before we finally made love. For that six months there was a lot of heavy making out but not even a hand job or a blow job. I wanted to suck his cock in the worst way but something just kept telling me to wait. He never even touched my breasts, and I so wanted him to. I wanted it bad, at this point, I was relieving myself at least once a day and sometimes more.
When we danced close, I could feel his erect penis pressing against me. He would put his hands on my round butt and pull me in tight, I had no doubt he was interested and it was good size. However, he continued to be the perfect gentlemen.
On our six- month anniversary, Baxter asked me if I would like to go out for dinner at a very nice hotel on the water in Boston.
I gave him a deep and passionate kiss and said, “Absolutely.”
He then asked, “Would you like to spend the night at the hotel.”
I was not totally sure where this was going but I suspected this would be the night for me to finally surrender my virginity and it would be to a man that I was absolutely in love with. I responded, “Yes, I would like that.”
It was a combination of wishful thinking and expectation that caused me to go on the pill a couple months back. I really can’t speak from experience but somehow, I can’t begin to imagine using a condom would be better than exchanging juices and having skin to skin contact.
When the day came, we spent the entire day together and were able to check in to the hotel at four o’clock. As usual Baxter held every door for me and treated me like his queen. I wanted for nothing. I had a very nice full-length evening dress that looked awesome on me. I was able to get away without wearing a bra but a simple lace thong was in order. The dress presented my 34D’s perfectly, just the perfect balance of cleavage to be appropriate but sexy.
While I dressed, I was hoping Baxter would sneak a peek or maybe even a feel but he didn’t. I was thinking, I sure hope he drops the gentlemen routine and it is in his plan to undress and make love to me.
Dinner and the drinks were fabulous and I totally enjoyed Baxter’s company. After dinner we took a walk down to the waterfront and for a moonlit stroll. We were at the end of the walk by ourselves and we started making out. Baxter put both hands on my ass and pulled me tight, there was no mistaking it, he was hard as a rock and I wanted him.
I turned away from him, he was behind me with his strong arms wrapped around. I could now feel his stiff cock pressing into my back. It had been over six months since I sucked a cock and I wanted so bad to turn around and take his manhood. I wanted that familiar feeling of a cock pushing against the back of my throat and the lust that I feel when the ribbons of cum are squirting into me. I did everything in my power to not attack him right here, right now.
His hands were on my waist and he was kissing and nibbling at my neck. I could feel his hands slowly working their way up my torso and onto my breasts. Finally, I thought. I have been waiting to have my breasts squeezed for six months. His hands were strong yet gentle. My nipples were so erect, I thought they might rip a hole in the shiny thin fabric of my dress.
I said to Baxter, “It’s time, please, take me up to the room and make love maltepe escort to me.”
He said, “My queen, it would be my pleasure.”
We walked through the lobby to the elevator, I didn’t feel nervous at all but, I had the sense that everyone in the lobby knew I was about to be deflowered. I was proud of myself, I wanted to tell everyone that I didn’t just giving myself to some jerk along the way, I waited for Baxter, my perfect gentleman.
When we got up to the room, Baxter had requested the romantic touches. There were silk rose peddles on the floor leading to the bed and a dozen or so on the bed, a bottle of wine chilling on ice and a small package that was wrapped beautifully. I was so pleased with the level of detail Baxter went to, it told me that this night was just as special for him as well.
We each took a couple minutes in the bathroom to freshen up. I let Baxter go first, he didn’t take long at all. I went in and debated, should I strip down to my thong or maybe nothing or should I let him take my clothes off. I decided on the later and went out to my man.
We embraced and he went right back to squeezing my boobs. I said, “Do you like my boobs?”
He smiled, and said, “They are beautiful breasts and I can’t wait to see them”
I gesture to untie the halter neck on my dress. He fumbled a bit but in no time, he had my tie undone and slowly let my dress slide down my body to the floor. I stepped out of my dress and stood before this beautiful man in my thong and high heels.
He said, “You are more beautiful than I have been dreaming,” he put his arms around me and gripped my ass pulling me in tight, we were kinda swaying to the soft music when he gestured for me to do a spin for him. Clearly, he wanted to check me out, so I made it a point of stepping away from him to give him a full look at what he is getting.
He didn’t know what to say, all he did was smile. I said, “My turn,” I started unbuttoning his shirt and removed it. His chest was magnificent, so muscular and smooth. I leaned in and took his nipple in my mouth and sucked it for a few seconds. His response told me I already found one of his spots.
Next, I reached for his belt buckle and his zipper. When I pulled his zipper down, much to my surprise his penis popped out. He was not wearing any underwear. He said, “even gentlemen sometimes have a little trick up their sleeve.”
I said, “I love it, you are full of surprises.” I took his penis in my hand, not sure how long it was but it was longer than any I had previously sucked on. I have had a few that are fatter but, I’m a fucking virgin, what do I know.
I gave it a kiss right on the head tasting his precum for the first time. Once again, I had to muster all my strength to not swallow it hole right them and there. I looked at it and said, “Don’t worry baby, I’ll be back you and we are going to be the best of friends.”
Baxter said, “May I remove your panties?”
I smiled at him and responded, “Baxter, I am yours, I love the fact that you are the most incredible gentlemen I have ever met but, from now on, when we are in the throes of passion, I would like you to take what you want, you have my permission in every regard.”
He didn’t say a word, I thought for a second that maybe I upset him. He picked me up and put me on the bed. He removed my heels and my panties. He spread my legs and dove his tongue deep into my virgin hole.
My pussy had been eaten by a girl who was soft and gentle, my gentlemanly Baxter ate me like it was his last meal. I said, “Baxter, that feels amazing and I’m ready to let go, I want my first orgasm to be with you inside me” He got up and slide his body against mine, our lips locked and for the first time I felt the head of a penis pressing against my opening about to penetrate me.
I said, “I want you inside me, please go gently.”
He leaned over to the night stand opening the drawer to get a condom. As he was ripping the package open I said, “I have a surprise or two myself, I went on the pill a while back anticipating this night, if it is ok with you, I would much prefer that we don’t use a condom, I would like to feel you inside me, I can’t wait to feel what it is like to be filled with sperm.”
Judging by the look on his face you would think he just won the lottery.
I could feel him at my entrance pushing in little by little. He reached down and took his shaft in his hand and rubbed it all over me spreading his precum. He entered me bit by bit and I could feel him going in. It hurt a little and I said, “go easy.”
He was back to being the perfect gentlemen, much as I wanted him to fuck me like a wild animal, I was happy that he was taking our time. I felt a sharp pain and winced, he eased up. It felt better and he was able to pump his entire length gently in and out of me.
It didn’t take long and he said, “I’m going to cum.” With that he thrust into me hard and I got this sensation mamak escort of being hot and wet. I’m going to guess I was just filled with his sperm. The sensation of him cumming put me over the top and I followed with my first orgasm with Baxter.
He basically collapsed on me; I could feel him still inside me but it was not as tight as it had been. Finally, he rolled off me and I could feel the cum dripping out. I looked down and saw a little bit of blood mixed in. I smiled at him and said, “Mission accomplished, I love you.”
Baxter was laying back on the bed and I had my head on his chest. This was my chance to check out my new cock. It was beautiful, it had a little more hair on it than I would like but we can work on that. It was responding to my touch, I asked him, “Would you mind if I took it in my mouth and sucked it.”
He smiled at me and said, “Babe, it is yours, you don’t have to ask permission.”
I turned my head away from him and took his cock head in my mouth. The combination of my pussy and his cum was delicious. I sucked it all the way down and gently stroked it; a mouth full of cum would have been wonderful but I wanted more cum in my pussy.
It didn’t take long and he was moaning again. I said, “I want you in my again.” Since we were new at this, we were focusing on the good old missionary position tonight. He rolled over and I instinctively spread my legs to let him in.
Despite the fact that I was pretty well lubed up he still took it slow and gentle as he entered me. Once he was all the way in me it felt really nice and I started thrusting toward him, before you knew it, we were really fucking. He was lasting much longer this time and I had two orgasms before he blasted me with more cum.
We kissed and cuddled most of the night but eventually fell asleep in each other’s arms.
I woke up laying on my side and Baxter was behind me, once I came to my senses and realized where I was, it was the most wonderful feeling of my life. I made love to the most awesome man in the world last night and I just woke up in his arms. I think he was asleep, and something I never thought about was occurring, his penis was rock hard and it was dripping wet wedged between my ass cheeks. I wondered, if this added bonus was something, I could get every morning.
Next thing I knew, Baxter was stirring. He was startled a bit and pulled away. I said, “No, put it back, you are as hard as a rock and I would not mind at all if you put it in me.” He did as I suggested and we were able to add another position to what would become a very long list. What a way to start the day.
Baxter got up to go in the bathroom and he put his robe on. When he returned, he took the robe off and slipped back under the covers. I snuggled up to him and said, “I have to ask you something, why was your penis so hard when you were still asleep this morning.”
He responded, “I’m sorry but that is just one of those things that happens to guys, we wake up stiff pretty much every morning.”
With excitement I said, “Oh please, don’t be sorry, I guess it is one of those things I will have to take care of.”
I got up to go to the bathroom but I didn’t put my robe on and I made sure he got a good view of my naked body. When I got back in bed, I said,” I saw you checking me out.”
He apologized, saying something about not wanting to make me uncomfortable.
I said, “Babe, I was not uncomfortable at all, I want you to enjoy me every way possible and the way I see it, being naked together is enjoyable. Baxter, I love the fact that you are the perfect gentleman but I would have really enjoyed watching you walk to the bathroom without the robe, both going and when you came back.”
He laughed and said, “I would be really happy to not wear a robe if that is something you would enjoy but the perfect gentleman in me got you a little present.”
I looked into his eyes and said, “A robe? I’m so sorry, I didn’t mean to mess up you surprise.” He gave me a package that was on the counter from the night before. It had the most beautiful short little robe with matching panties, that I have ever seen. It was white with pink lace trim, almost sheer and very short. “It is beautiful,” I got up to try it on and he said something about robes not being allowed in our bedroom. “I think we will allow this one, but sometimes I might just forget to put the panties on.”
He said, “Works for me, you are absolutely beautiful.”
Apparently, he took this to heart because neither one of us ever worn a typical robe again, at least not in our bedroom.
Baxter called for room service, in about a half hour breakfast arrived. Baxter being the gentleman that he is made sure I was comfortable in bed under the covers before letting the waiter in. Breakfast was delicious.
We freshened up a bit and Baxter said, what would you like to do now, we have all day and we don’t have to check out until tomorrow. This was a surprise to me, I assumed this was a one-night stay. I was delighted when I found out we were staying.
I said, “If it were up to me, I would jump right back in that bed and continue making love to you all day and night.”
Baxter smiled and said, “That sounds awesome but I need to recharge a little.”