Meeting Her Boyfriend

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Soon to be cuckold has to ask for a favor.
8.3k words
4.37
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Part 1 of the 2 part series

Updated 03/10/2024
Created 01/31/2024
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sissylena
sissylena
34 Followers

Warning: This story is about a wimp husband and his frustrated wife. If stories about Cuckolds, Wife Watching, Cross Dressing or Humiliation bother you, stop reading now.

The parking lot of the bar is half full already and the band hasn't even started. It's a Friday evening in October near the Illinois/Wisconsin border, so it's cool out. It's my wife's birthday and she wants to go out to her favorite bar. It's just a dive bar that's north of town and a couple miles from our house. A sports bar with music on the weekends, it has a reputation of being a meat market with mostly twenty and early thirty something jocks and rednecks. It's on the two lane highway near the gas station a couple miles from our house and it's named after some old car or something. We recently moved from the crowded city to a community out in the country. We live in a small neighborhood that's surrounded by farms and lakes and lots of bars. Almost everyone around here drives a pickup truck or some sort of SUV, so my little Prius definitely looks out of place parked near the dumpster.

My wife Lorelai is thirty nine and I'm thirty seven. We've been married for almost two years and met on a computer dating site. Her profile said she worked for a large tech company and was in charge of a large group of techs. She described herself as outgoing and extroverted and that she likes to be in charge. She wrote that she was ready to settle down and was looking for someone sensitive and loyal who was a homebody and would treat her like a queen. I was surprised when such a beautiful dynamic woman reached out to me for the first date and thrilled when she proposed to me after only a few months of dating. She told me I was just what she was looking for in a partner and I was smitten with her from the first date.

We have a good marriage although I sometimes wonder why she settled for me. I guess they say opposites attract because she's outgoing, flirty and gorgeous. On the tall side at five foot nine and voluptuous with an great figure she keeps in shape with regular workouts and a yoga routine, Her adorable face with bright blue eyes and full lips is framed in a blonde bob hairdo that stops just above her shoulders. Long legs, full rounded hips and butt and thin hourglass waist are topped off by two enormous breasts that stick out and defy gravity. I've overheard other men talking about her being 'built just like a big busted Barbie doll'.

My mother had three daughters in a row and then had me. My father left her before I was even born, so Mom raised us on her own and worked full time while my older sisters took care of my youngest sister and me. Being on the poor side, I wore a lot of hand me downs, including my sister's panties growing up, so I got teased a lot and didn't have any close friends who were boys. The only male role models I had growing up were when Mom's or my older sister's boyfriends were over and they mostly ignored me or teased and humiliated me for not being manly enough.

We were all expected to pitch in and do the housework so I learned to clean and sew and cook. My oldest sisters, being bossy like they were, usually talked me into doing more than my share of the housework in exchange for not beating me up. Later on after they were gone and I was eighteen, my youngest sister who is a year older than me would get me to do her share by letting me peek in on her and see her in various forms of undress. She knew I had recently discovered porn so she knew I would enjoy a show. She developed into a real exhibitionist and was even a stripper for a while to pay her way through college.

I'm quite passive and quiet and not at all what one would call manly. I used to wear my hair short until I met Lorelai. She thought I would look better with longer hair, so now it's down to my shoulders and I keep it in a ponytail most of the time. Besides only being five foot six inches tall, Mother Nature couldn't decide about me when it came time for puberty. When I was in middle school and all the other boys were getting wider shoulders and muscles, my shoulders stayed narrow and my hips got wider and my butt got bigger. The other boys all grew body hair and eventually had to shave by college. I still don't shave and have very little body hair and only a small light patch of pubic hair. My breasts became very sensitive to the touch and started to sprout and darken around the nipples. They grew to full A cup and developed quarter sized areolas and large nipples that grow as long as thimbles when stimulated. It's very embarrassing and I always wear loose oversized shirts and undershirts to try to hide them. I also have a very small penis that stopped growing even before puberty. When it's hard it's only two inches and looks like a baby carrot. When it's soft it retracts into me like a turtle head, so all you can see is a little nub above the small ball sack that dangles between my legs.

From behind I'm easily mistaken for a woman and it's happened quite a few times over the years. It's been happening a lot more with my long hair. Because Lorelai is so beautiful and outgoing, men will come up and just start talking to us like we're both women before they realize I'm not, much to her and the men's amusement and my embarrassment.

Because of my physical appearance I haven't exactly been a chick magnet. My dating life was sparse to say the least. When I was nineteen I worked one summer in a small office with all women. There was a woman there named Susan who I was friends with who was divorced in her mid thirties. Susan was a little on the chunky side but she had very large breasts that she liked to show off in low cut tops. One day she caught me peeking at her cleavage and offered to show me her breasts if I drove her home. When we got to her house, she took her top off and told me to take off my pants and looked surprised when she saw my little penis. I guess my embarrassment showed because she reassured me there were other things we could do besides sexual intercourse. She told me if I would 'go down' on her, she would teach me how to please a woman with my mouth. I was a very eager student and learned quick. I started picking her up and driving her home and Susan made me suck and lick her vagina almost everyday after work all summer until I went back to college in the fall.

The few women who would date me weren't interested in me sexually, other than my oral skills, especially when they learned of my lack of equipment. When I was in my twenties and thirties I went to topless dancing bars and gentleman's clubs a lot just so I could watch the nearly naked and sometimes bare women and fantasize about them. Because of my small size and feminine build, horny older men at those clubs would eye me strangely sometimes rubbing their crotch as they leered at my body. Some even approached me to talk to me, calling me honey and sweetheart and offering to buy me drinks if I danced for them or went into the men's room with them. Didn't they know I wasn't a girl? I told them I wasn't gay, but I would come home and masturbate while fantasizing about the naked women and thinking about the big bulges in the men's pants that I'd seen. I also continued to watch a lot of porn online. I especially liked watching women being dominated by men who had big penises. I would watch them sucking off and being penetrated by big manly men with big manly penises and I would masturbate until my little penis was sore. I was then and still am a chronic masturbator, playing with my tiny penis daily or sometimes multiple times in a day.

When I turned thirty five I dared myself to sign up on an online dating sight and didn't think I would get a response. A week later I received a date request from Lorelai and we dated briefly and she proposed soon after. Soon after we married she got a big promotion at work and her job changed. She started making a lot more money than me but had to travel out of town every week for over a year. She would be gone all week and come home on the weekends. In addition to my menial office job, I started doing all the cleaning and laundry and cooking so she could recharge from her long week away. She was always so tired when she got home. She said it was because her bosses always made her work far into the night on those business trips. It pleased her that I doted on her and was so willing to do the domestic chores she hated. I didn't mind, in fact I love doing the housework and cooking for others, so I just continued doing it even after she stopped traveling.

Tonight she's wearing a tight black sort of see through top with a plunging neckline displaying a bright pink plunge bra that has her showing an enormous amount of cleavage. Under her short black skirt I think she's wearing matching pink panties. She's wearing black thigh high stockings, pink four inch stiletto heels and lots of makeup. She always dresses very suggestively when she comes here. Walking behind her watching that butt of hers swaying back and forth only makes me wish she would dress like that for me. She towers over me as I hold the door open for her. As she enters the bar she turns and looks down at me wagging her finger and with her bright pink lips rather firmly says,

"Now remember why you're here with me tonight, and don't you dare embarrass me in front of my friends."

I'm here with her tonight so I can meet her boyfriend, or as she would say, we are all here so her little wimp husband can meet the real man who's going to take care of her sexual needs. She told me I would need to ask him, in person to his face, to start having sex with her, again. I also have to tell him I'm unable to satisfy her with my useless penis.

Because it's her birthday, Lorielai got to choose where we went and what I'm wearing tonight. She bought the outfit special after she told me I needed to wear something that wasn't threatening to her new boyfriend when I meet him. Right, like I would be threatening to a guy a foot taller and a hundred pounds heavier. Tonight I'm wearing a pair of tight low cut women's leggings, a tight knit top that doesn't even come down to the top of my jeans leaving my bare midriff exposed. She let me wear a jacket originally to hide my breasts sticking out, but told me to leave it in the car. She also has me wearing my hair loose and hanging down, styled in a long curly bob instead of pulled back. Simple woman's ballet slippers complete my outfit so I look like a girl without any makeup on. I felt embarrassed even walking out of the house dressed like this but would soon learn it was only the beginning of my humiliation.

Lorelai has a lot of friends. She's still friends with a lot of past workmates and she's always telling me about them. Since she works in a male dominated business, most of them are men who she just chats with online to catch up on gossip and stuff or discuss old times. I didn't think anything of it when she mentioned a guy named John who she said was also someone she used to work with.

One day she asked me if it was okay if she and John met in person to just talk and catch up. I said it was okay with me and thought they were going to meet at the coffee shop in town. On the day they were to meet, she informed me that they were meeting at a bar so they could both have a drink and relax. I don't drink much so I was happy she had someone to drink with. After the first meeting, she started seeing him three or four nights a week while I stayed home to catch up on my housework and to watch my television shows. She also started dressing more provocatively. She started wearing low cut tops and short skirts, even stockings and high heels which she never wore for me, and always makeup, lots of makeup.

At first she said they just drank and talked about old times. Then one night after she got home from one of her dates we were lying in bed. I was naked playing with her breasts in her unbuttoned top like I love to do. She started gently stroking my penis with one finger and her thumb teasing the head while she squeezed my balls with her other hand. God, it felt so good! She looked down at me and said, "Honey, I have something I need to tell you and I hope you don't get upset."

Lorelai had a concerned look on her face and I started to worry a little. She went on to explain, "Well, tonight when John and I were saying goodbye, he took me in his arms and he kissed me and.... and I kissed him back and, well, I really liked it."

She waited for my reaction and when I didn't get upset she looked relieved. In fact when she told me about what they had done, my dick started twitching and leaking a little. She went on to reassure me, "You know I love you and would never leave you. You're a wonderful husband and perfect for me. I just have such a good time with him talking and stuff and I really want to keep seeing him, but I'll stop if you really want me to."

Lorelai always gets what she wants and I knew she would find a way to see him anyway, It also kind of turned me on hearing about how they kissed, so I reluctantly told her, "No honey, I'm glad you have old friends you can talk to and I want you to keep seeing him if you want, and besides, it's just a good night kiss."

I knew I should be jealous, and I kind of was, but my penis had other ideas and I was getting really turned on thinking about my Lorelai with another man. I then asked, "I want you to tell me honestly, does it turn you on to be with him?

She thought about it for a few seconds, "Oh yes, very much." A sly smile appeared on her face, "But I have more to tell you,"

My little dick was wet from all the excitement as she continued, "When he kissed me he pulled me tight against him and pushed the sides of my breasts together with his arms so tight my breasts were coming out of the top of my blouse, right there in front of everyone."

"I bet he liked that," I quipped, "Did he get excited?"

"I could feel his big boner rubbing against me as we kissed," she gushed.

She started stroking me lightly while I squeezed and kissed her luscious breasts. Her nipples were both swelled up and hard. I was getting more turned on than usual by our discussion. She reached under her breast and pushed it up into my face, "Honey, how would you feel if I let my boyfriend touch these, what if he wants to grope and paw me with his big strong hands?"

I pondered what she asked and the truth is, thinking about her being with other men, real men, and those real men molesting and fondling her was getting me really hot. All I could do was moan as she smiled and nodded and got that look like a lightbulb went on in her head and she seductively continued, "What if he wants to touch me other places, like down there, would that turn you on?" She started stroking me faster. "What if my new boyfriend wants me to touch him down there, do you want me to touch my boyfriend's big cock?"

The thought of my wife's little hand wrapped around another man's big penis pushed me over the edge and I dribbled all over her hand.

"Oh my, looks like someone approves of me having a boyfriend," she cooed as she fed me the cum off her hand. I told her I was good with it as long as she talked to me about what they did.

Lorelai let me know when we met that she loves having sex and has a huge appetite for it. She told me she would rather give oral than receive and loves having a penis in her vagina most of all. We used to have intercourse when we were dating and she acted like she enjoyed it, but soon after we got married she stopped letting me put my penis inside her. She complained she couldn't really feel my little boy dick inside her and that I came too quickly. I usually lasted only a couple of minutes before my dick would betray me and dribble out the little cum that would be made by my tiny little balls.

I really love to perform oral on her. I love the taste and smell and the way it feels on my mouth. I love to lick her juices and stick my tongue up in her hole. She told me she doesn't normally want men to do that to her, that she likes a penis in there. Because my penis is so small and useless, and she knows I really love sucking, she sometimes lets me go down on her. She told me she had let a lesbian roommate in college suck her and that I sucked as good as her. Lorelai's vagina gets really wet when she's excited and squirts when she has orgasms, so my face always gets wet when I eat her out.

What really gets her off is when I use a fake penis on her. It's much larger than mine and its made of rubber and is very stiff. She even bought a head harness so she could make me wear the thing on my head. She makes me lie on the bed and position the harness on my face with the dildo in it pointing up. Then she squats down over my face with her bare vagina and lowers herself until the penis is inside her. She uses her legs to raise and lower herself until she orgasms and squirts all over my face. She said it's good exercise for her legs. Most of the time I just use my hands to ram the large penis in and out of her. I love to watch how it spreads the lips of her vagina as it enters her and how she moans and thrashes about until she squirts all over my hands.

Lorelai used to suck on my penis and is really good at it. She said she didn't mind my little dick because she can get the whole thing including my little balls in her mouth. She would put it all in her mouth and run her tongue all over it and then bob her head up and down while she sucked. Her mouth is wonderful! It only took a couple minutes before I started to cum and she took it out of her mouth and let it run over my stomach. Since she started touching her boyfriend she has stopped touching and sucking my penis and has forbidden me to touch her breasts and vagina. She told me that a real man is in the picture now and that her new boyfriend doesn't want anyone else touching her without his permission. She lets me masturbate in front of her while she talks about him and when I cum I lick it up and swallow it. She says it's good protein and it pleases her to watch me do it. She tells me a good spouse should always want to please her. At first I didn't want to eat my cum, but it actually tastes kind of good and now I look forward to her making me eat it.

After the kissing story, my wife and her boyfriend started meeting every night. He even picks her up in his truck so she won't have to drive and they have more time together. He has one of those jacked up pickup trucks that she has to climb up to get into. She leaves the house wearing a skirt so short I can clearly see her panties as she climbs in. I'm sure the neighbors notice them too, as well as the redneck driver whose truck my wife eagerly climbs into and leaves in without me.

It's been two weeks since the kiss and she's been staying out later and later with him. She told me that it would please her if I greet her at the door naked when she gets home. She always remains dressed in her slutty outfits and describes in detail what they did that night while I stand naked in front of her with my hands behind me. It drives me crazy with lust and humiliation when she describes the things they do. I'm not allowed to touch her at all or touch myself without permission. The other night she told me they've started making out in the bar. Her boyfriend makes her remove her panties in his truck when they're together. She told me he'll reach up and rub her bare vagina under her skirt and sometimes insert his fingers while she rubs his penis through his pants. Sometimes he even takes his dick out of his pants when they're in his truck or at the bar if no one is around and Lorelai gives him a hand job and strokes him right there in the bar. When she tells me these stories my dicklette drips without even being touched.

Lorelai could see that I was starting to really get into this and going along with her little plan. Two nights ago when she returned from her date she said we needed to have another talk. "How would you feel if John and I started having sex again?"

sissylena
sissylena
34 Followers