First Time Being a Sugar Daddy

My First Sugar Baby Experience

(Introduction, my first story submitted. Please give honest feedback. Most of the story is true and was my first time having a Sugar Baby)

After a decade of a sexless marriage, and only being a caretaker for my disabled wife of 25 years, I decided that I need companionship and intimacy that I no longer had at home. I was depressed coming home after a long day of work, to face more work and chores at home and no appreciation. I had heard an advertisement about Sugar Relationships where a Sugar Daddy, an older gentleman, would provide support or gifts to a Sugar Baby, a younger girl in exchange for intimacy and companionship. This sounded exactly what I needed, though it made me nervous, as growing up, I really didn't date much and was kind of shy person.

I decided to throw caution to the wind and signed up to a sugaring website. I created an online profile, posted my picture, as well as purchased some credits to message potential Sugar Baby's. After a week or so of browsing, I received a message and access to this cute Asian girl's secret pictures. Her secret pictures were very sexy, picture of her in two different lingerie sets. She was new to the site as well, according to her post. I replied to her message, and soon we were messaging back and forth. For privacy, we decided to move off site with our messaging.

In her text message she said her name was Jennifer. After a couple days of texting, I asked Jennifer if she would like to meet up in person. She said sure, how about we meet for coffee? I asked her if tomorrow would work to meet for coffee at a Java House near her? She said sure, how about 10am tomorrow? It will be near my school as well she replied.

The next morning, I anxiously waited for Jennifer outside of the Java House at our agreed meeting time. When she arrived, we greet each other with pleasant hellos and entered the coffee shop. I ordered us coffee while she found us a quiet table so that we could talk. We talked for a good hour getting to know each other. She looked very young and innocent, dressed in a nice sweater and blue jeans. I found Jennifer very cute and was interested in getting to know her more. I enjoyed our conversation we had together. I had asked her how she found out about the site, and she told me her friend from school told her about it as she had been on it for a few months making some extra money.

She told me her friend had met a guy on the site, and they would meet two or three times a month. I asked her what they did for their meetups, she told me they would meet in a hotel room and have sex and he would then pay the agreed upon allowance. This sounded just what I am looking for. My cock was getting hard thinking about having sex with this pretty Asian girl sitting in front of me, hoping she would be interested in an arrangement like this with me. I told Jennifer that I was enjoying our conversation and am looking forward to getting to know her more, and she told me she would like that too.

She asked me if I was willing to do a pay per meet arrangement with her. I told her I would love to have an arrangement with her and I mentioned an amount that would work for me for a pay per meet date. Jennifer told me that my offer of the PPM would be acceptable to her. I told her that I was looking to meet two to three times a month. She said that was good with her, and she would let me know when she could meet. We finished our coffee and walked to the parking lot. We parted ways with a hug, and I told her that I was so glad to have met her and was looking to seeing her again.

Later that afternoon, I sent her a text letting her know how much I enjoyed her company today and would look forward to seeing her again soon. She replied it was surprisingly nice for her and was looking forward to seeing me again. She said our meet was so soon, that next time she wants to be prepared with getting her hair and nails done and have some sexy lingerie.

Our texting went on back and forth daily for a couple of weeks. Jennifer had let me know, that she was busy right now with school, and family things right now and for me to please be patient with her. I told her no problem, just let me know when you are available.

On the third week of communicating by text with her, she asked me what my schedule was like to meet. I told her that I was flexible, and asked if she was interested in meeting for lunch or dinner soon. She replied if I wanted to get a room, that was fine with her unless I just wanted to meet for lunch. I told her a room would be nice if she was good with it. She said yes, of course, and she let me know she could meet on Wednesday or Thursday afternoon if that would work for me. I enthusiastically said Wednesday would be perfect. She said fabulous, and confirmed with me that she would get her agreed upon allowance for meeting. I assured her that I would take care of her allowance as promised. I thought to myself, wow, this young innocent Asian cutie wants to meet at a hotel on our second meetup.

The thought of her wanting to meet me in a hotel, with the possibility of me fucking her, gave me a raging erection. I couldn't wait to see her. We agreed upon 1pm to meet at a hotel that was halfway between us to make it convenient for both of us for our meet tomorrow. I made our reservations that afternoon, gave her the address and confirmed with her by text that night that we were good for our meet tomorrow. She confirmed and let me know she was excited to see me and wanted to please me. I told her I would give her our room number tomorrow after checking in.

On the way to the hotel, I stopped to pick up flowers for Jennifer, a nice card, and a package of condoms in case I was to get lucky. I arrived and checked into the hotel room at noon on Wednesday taking an extended lunch today. I texted Jennifer to let her know our room number. I placed the bouquet of roses and the card that I purchased that contained her allowance in it on the dresser. I also placed the condoms that I purchased on the nightstand in hopes that we were going to fuck this afternoon. I thought to myself, why else would she suggest a hotel room this afternoon if she wasn't interested in being fucked. I was hopeful any ways. I quickly got undressed and started the shower. I wanted to shower good and wash and shave my balls good just in case Jennifer gave me a blow job.

While I was washing my balls and cock, I started stroking myself thinking about fucking and licking Jennifer's Asian pussy. I stopped stroking myself so that I wouldn't cum in my hand. I wanted to save myself for her sweet Asian pussy. I quickly finished my shower and got dressed. Fifteen minutes later, I hear a soft knock at the door. I opened the door to see Jennifer standing nervously at the door. I told her to come in and how beautifully she looked when I laid my eyes on her. She looked so elegant in her black sexy dress, the sexy nylons, and the black fuck-me high heels. Jennifer looked amazing standing at 5 feet 7 inches, with her 34D tits and her trim waist and a squeezable cute butt. The bio she posted online had stated she was a 35-year-old curvy Asian girl. Her outfit showed off her curves. I, on the other hand, am white, 5 feet 9 inches with an average body. She looked young compared to me being 57 years old.

We greet each other with a hug. I give her a card with the promised allowance in it, along with a bouquet of red roses. She was so happy with the roses. We stand and look into each other's eyes. She tells me that she hopes I like her lingerie she is wearing under her dress. She tells me this is the first time to do something like this and to get undressed in front of a guy. I ask her if I may kiss you, and she responds that she is not good at kissing, but says ok. I lean in for a kiss, and it was wonderful.

I asked her what her boundaries are or what she is open to as far as intimacy. She tells me that she is open to try anything, except being fucked in her ass. Jennifer tells me that she only wants sex in her pussy only. She tells me that she has very little experience with sex so be patient with her. Jennifer got my cock hard just thinking about fucking her sweet Asian pussy. I let her know that I brought condoms for our rendezvous. She tells me that they are not needed unless I wanted to wear a rubber, since she is on birth control. She tells me that she wants to feel my bare cock in her pussy without wearing a rubber if that is ok.

She tells me she was preparing herself for her boyfriend to have sex with him, but it never happened. I tell her that I have not had sex or had my cock in a pussy for 11 years. I tell her she doesn't have to worry about getting any STD's from me since I have not been with anyone for the last 11 years and that was with only my wife before her surgery. Jennifer said she is STD free too as she has not had any sex with anyone. I was so excited knowing that I would get to fuck her virgin Asian pussy raw this afternoon.

She asked me if I would like a massage. I said sure, I would love one. She tells me to get undressed, I remove my shoes and socks, pants, my shirt and finally my underwear. I am now standing naked in front of this beautiful Asian girl. I am getting aroused being naked in front of her as I watch her remove her fuck-me heels. After removing her heels, she unzips her dress and lets it slip off her shoulders and lets it drop to the floor and steps out of it. She bends over from the waist with her back to me to pick up her dress, I look at her thong buried in her ass crack and a hint of her pussy lips hanging out the sides of her panty. She is making my erection even harder. She turns around facing me, she looks so lovely standing there in her black lacey bra with her nipples showing through the lace, and the sexy lace black thong panty that is showing a hint of pubic hair on her mound and her pussy lips hanging out the sides, with a garter belt holding up her sexy nylons.

She asked me if like what I see? I tell her she looks beautiful standing there in just her sexy lingerie. She said she could tell I liked her lingerie; she noticed my cock became fully erect. She told me that she is happy that she turns me on. She also noticed that I shaved my pubic area. I told her yes, I wanted to have a clean look for you for our meet. She said that is cool, and that she never has seen a guy with a shaved balls and pubic area before. She told me her ex-boyfriend was very hairy down there.

She asked me if I'm ready for my massage, I tell her yes. She tells me to lay on the bed face down. I slide up on the bed face down, letting my cock rub on the bed as I slide up on it. I leave my legs spread a little bit so that my balls are exposed from behind. She tells me that she brought baby oil, and if I minded being massaged with the oil. I tell her not at all. Jennifer crawls on the bed beside me and squirts oil all over my back. As she is massaging my back, I let my hand wander to her leg near me and kind of rub the inside of her leg trying to reach her pussy. She closes her legs tight restricting me. Her leg felt so smooth with her nylons on, and I could feel heat radiating from her pussy when I tried touching it.

Jennifer was massaging me with only wearing her sexy bra, thong panty, garter belt, and nylons. It was so erotic watching her in the mirror massaging me. After a bit, she moved to straddle me. She was sitting on my ass while massaging my back and neck. Her panty clad pussy felt so nice on my ass, and I could feel the heat and wetness from her pussy. After finishing my back, she stood on the bed and changed positions so that she faced my legs. She scooted back sliding her covered pussy on my back so that she was sitting on my mid back. I could feel her pussy on my back, and it felt wonderful.

She started massaging my butt and would brush the crack of my ass with her fingers causing me to let out a moan. It felt so wonderful. She then let her hand trail down my left leg and started massaging the back of my thighs. I laid there hoping that she would rub my balls while massaging me. I spread my legs a little further apart hoping she would get the hint. She did, she allowed her fingers to brush against my balls while massaging me. She then moved on my right leg and repeated the same strokes lightly touching my ball sack. I let out a moan each time she touched my balls.

She asked if I minded what she was doing. I told her it felt wonderful and that I loved her touching my balls. Next, she got off me and off the bed and started massaging my hamstrings. She would do long strokes starting at my ankle and work her way up the inside of my thighs brushing my balls again. I could feel her pussy brush over my heel as she leaned forward. My cock was so hard from her teasing my balls and her pussy touching the heel of my foot as she rubbed. I told Jennifer that she was driving me crazy and that I couldn't wait to fuck her with my hard cock. She just giggled when I told her that and told me that my potty mouth was making her wet and horny.

After massaging my feet, she asked me to turn over and that she would massage my front side. I did as she told me. My cock was standing straight up from the erection she caused me. She asked me if she was the cause of my erection. I told her yes, you teasing my balls and feeling your warm wet pussy on my back made me excited. She moved to the front of the bed and moved so that my head was between her legs. She leaned over me and was putting her bra covered tits in my face as she massaged my chest. I took in the sight of her beautiful tits, inhaled her perfume from her cleavage, and would try to kiss her bra-covered tits when she leaned close enough for me to reach them.

As she massaged my chest, she would hover down over my stomach and massage my stomach and would tease me by massaging my pubic area and grazing my cock at the same time. She commented again how she liked me being clean shaved in my pubic area and my balls and how soft it felt. She said it really allowed her to see my cock completely. Before finishing my chest, stomach, and pubic area, Jennifer slid her hand down and cupped my balls and softly stroked my hard cock. I almost came right there in her hand when she did so. She stopped before me cumming and moved down to massage my legs.

While massaging my legs, she did as she did before, and would massage the inside of my thighs so that she would lightly touch my balls to keep me hard. It was the most erotic massage I ever had, looking at this Asian cutie in her lingerie massaging me. She let me know she was finished massaging me. I asked her if I could give her a massage. She said that would be wonderful, but only her back.

She said please be gentle and patient with me, as I have never been naked in front of a guy before, and you are the only guy I have seen completely naked. I asked her if her and her boyfriend ever had sex before and she said no. She told me he wanted to, but she had always turned him down. The most he would do would rub my tits on the outside of my shirt and occasionally I would let him put his hand up my shirt and under my bra so that he could fondle my tits. It was ok for me, but nothing that I looked forward too. A couple of times, he would put his hand down my pants and into my panties and he would finger me, but he was always rough and I didn't care for it at all. Most of the time, I would only let him touch my pussy from the outside of my clothes. He would get so frustrated, but I was scared to go any further. To keep him happy, I would give him hand jobs. Once I gave him a blow job, but since he came in my mouth without warning, I never wanted to do it again with him. Plus, I didn't care for all of his hair down there touching my face and nose. It was kind of disgusting she told me.

She said her cousin said that she needed to loosen up and give him sex or he would leave me, so she said she went to the clinic to get on birth control. She told me she had an IUD place in me. She said it felt uncomfortable getting that done. She told me the day after getting it put in, they had gone on a date, and he tried to put his hands down her pants, and she told him to stop as she was on her period and sore, and that he got mad and took her home. She told him she was on her period because she was sore from the procedure and wasn't quite ready for sex since she was spotting a bit from the procedure. She said she was going to surprise him for his birthday and let him fuck her then, but he broke up with her before his birthday. I told Jennifer it was his loss and my gain.

Jennifer told me that she joined a website for Sugar Baby's to hook up with Sugar Daddy's to find an understanding older gentleman and to make some extra money since she is not working. She did say that she was nervous about the sex part but wanted to give it a try with the right daddy. I told her that I was so happy that our profiles matched and that she reached out to me. She giggled, and asked if I had an Asian fetish since I replied to her. I said no but found you very pretty and liked your profile. I felt that our desires had matched each other's. I assured her that I would always treat you with respect, and I would never hurt you or do anything that was unpleasant to you. I told her that I would never cum in your mouth unless you asked me too. She was happy for me being understanding but was unsure if she could give a blow job again. I told her that was fine. I told her that I am lucky and honored to be the first one to fuck you and pop your cherry. She laughed at my comment and said she hopes I will enjoy her Asian cherry.

I finally said, let's start your massage. Jennifer slowly unclasped her nylons from her garter belt, slowly rolled her nylons off one leg at a time exposing her beautiful painted toenails. She removed her garter belt and then her bra. She looked so adorable standing there in her lacy thong panty. Her tits were the most beautiful tits that I ever looked at. They looked firm and well-rounded with beautiful dark brown areolas. I told her that she looked amazing. She said she would leave her panty on for now if that was ok. I told her sure, that was fine.

She crawled up on the bed face down with her legs close together, unlike how I had mine. I started with Jennifer's back and applied baby oil to her back. I rubbed the oil deeply into her back and into her shoulders using my hands, knuckles, forearms. She is telling me how good it is feeling. I rub her lower back, cautiously getting near the waistband of her thong. She is softly moaning. I move lower to her butt cheeks and start rubbing and kneading her butt around her thong covered butt. She is telling me how much she is enjoying her butt being massaged. I start paying more attention to her ass giving it soft squeezes. I then start massaging the upper backside of her thighs with ample amount of oil. I am gradually able to get her to spread her legs a bit. I rub and squeeze her legs, gently and slowly creeping up to the junction of her legs almost touching her panty covered pussy lips.

I can feel the heat radiating from her pussy. The heat I feel causes my cock to get hard again. I slowly keep rubbing her inner thighs until I brush her pussy, she lets out a gasp. She doesn't seem to stop me, so I keep rubbing up and down each inner thigh intentionally touching her pussy. Jennifer keeps moaning with each touch of my hands on her pussy and I can really feel how hot her pussy is. I move back up to her butt cheeks and massage them some more. I dip my fingers under her panties to rub where they are covering her. She says please be careful not to rip the delicate lace. I ask her if I may remove her panty so that I don't ruin it and I did let her know that I would love to buy her more sexy undies if she would like me too. She said to go ahead and remove her panty carefully.